Journal of Pharmacy And Bioallied Sciences
Journal of Pharmacy And Bioallied Sciences Login  | Users Online: 4269  Print this pageEmail this pageSmall font sizeDefault font sizeIncrease font size 
    Home | About us | Editorial board | Search | Ahead of print | Current Issue | Past Issues | Instructions | Online submission

Year : 2010  |  Volume : 2  |  Issue : 2  |  Page : 64-71 Table of Contents     

Structural modifications of quinoline-based antimalarial agents: Recent developments

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi-110 062, India

Date of Submission18-May-2010
Date of Decision19-May-2010
Date of Acceptance14-Jun-2010
Date of Web Publication2-Aug-2010

Correspondence Address:
Sandhya Bawa
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi-110 062
Login to access the Email id

Source of Support: None, Conflict of Interest: None

DOI: 10.4103/0975-7406.67002

Rights and Permissions

Antimalarial drugs constitute a major part of antiprotozoal drugs and have been in practice for a long time. Antimalarial agents generally belong to the class of quinoline which acts by interfering with heme metabolism. The recent increase in development of chloroquine-resistant strains of Plasmodium falciparum and failure of vaccination program against malaria have fuelled the drug discovery program against this old and widespread disease. Quinoline and its related derivative comprise a class of heterocycles, which has been exploited immensely than any other nucleus for the development of potent antimalarial agents. Various chemical modifications of quinoline have been attempted to achieve analogs with potent antimalarial properties against sensitive as well as resistant strains of Plasmodium sp., together with minimal potential undesirable side effects. This review outlines essentially some of the recent chemical modifications undertaken for the development of potent antimalarial agents based on quinoline.

Keywords: Antimalarial activity, chemical modifications, quinoline

How to cite this article:
Bawa S, Kumar S, Drabu S, Kumar R. Structural modifications of quinoline-based antimalarial agents: Recent developments. J Pharm Bioall Sci 2010;2:64-71

How to cite this URL:
Bawa S, Kumar S, Drabu S, Kumar R. Structural modifications of quinoline-based antimalarial agents: Recent developments. J Pharm Bioall Sci [serial online] 2010 [cited 2022 Dec 7];2:64-71. Available from:

Malaria is one of the most widespread diseases in the world besides tuberculosis and AIDS. It is estimated by World Health Organization (WHO) that about 40% of the world's population presently lives under malarial threat and approximately 300-500 million cases of malaria occur annually, leading to 1-3 million deaths. Mortality is particularly high for children under the age of 5 years, accounting for about 25% of childhood deaths in Africa. [1],[2],[3] Malaria is caused by different species of Plasmodium, of which Plasmodium falciparum is the most virulent human malarial parasite and others include Plasmodium vivax, Plasmodium malariae and Plasmodium ovale. A major reason for the continued severity of the worldwide malarial problem is the increasing resistance of malarial parasites to the available antimalarial drugs such as chloroquine (CQ). Although continued attempts to develop a vaccine for malaria are ongoing, drugs continue to be the only treatment option available.

Quinoline containing compounds have long been used for the treatment of malaria, beginning with quinine. Systematic modification of quinine led to the potent and inexpensive 4-aminoquinoline drug, CQ, and other related drugs [Figure 1]. After the worldwide development of drug resistance to CQ, rational approach in chemistry and screening efforts produced mefloquine, another quinoline containing compound that was highly active against the CQ-resistant (CQR) strains of P. falciparum. Since the development of mefloquine, there have been several reports of new potent quinoline compounds. Most of these contain the 7-chloroquinoline nucleus of CQ and vary in the length and nature of their basic amine side chain. Currently, compounds such as amodiaquine (AQ) and AQ-13 are promising leads for the development of new drugs. [4],[5]

With a chemical structure significantly different from that of quinoline-based drugs, the natural product artemisinin and its derivatives have attracted the attention of many different groups. The mechanism of action of artemisinin antimalarials is reported to be devoid of significant clinical resistance, with its 1, 2, 4-trioxane as active motif. 1, 2, 4-trioxane as active motif of artemisinin has served as a template for the design of synthetic peroxide-containing drugs. [6],[7]

In drug designing programs, an essential component of the search for new lead is the synthesis of molecules which are novel, yet resemble known biologically active molecules by virtue of the presence of critical structural features essential for desired pharmacologic effect. In this review, we have highlighted some of the antimalarial drug discovery efforts related to quinoline nucleus, which are currently being developed at universities, research institutions, and pharmaceutical companies worldwide.

   Quinoline Chalcones Top

The antimalarial activity of chalcones was first noted when licochalcone A 1 , a natural product isolated from Chinese liquorice roots, was reported to exhibit potent antimalarial activity. Later on, it was observed that good antimalarial effects were exerted by alkoxylated chalcones with polar B rings, in particular, those substituted with electron withdrawing groups or those incorporating quinoline rings. [8] Since then, a number of chalcone derivatives containing quinoline and other heteroaryl moiety have been synthesized and evaluated for potential antimalarial activity. Charris et al. [9],[10] have reported a series of E-2-quinolinylbenzocycloalcanones 2 and evaluated their activity to inhibit β-hematin formation and the hydrolysis of hemoglobin in vitro and their efficacy in rodent Plasmodium berghei. Inhibition of β-hematin formation was minimal when a hydrogen or methoxy groups were present on the position 8 of the quinoline and position 4′ of the indanone ring. The study was further elaborated by synthesizing quinolinyl chalcones having dimethoxy group 3, 4. [11] Similarly, Liu et al. [12] have synthesized multi alkoxylated chalcones 5 on ring B and evaluated their in vitro action against P. falciparum (K1) in a [3H] hypoxanthine uptake assay. Trimethoxy, dimethoxy and methoxy analogs showed good in vitro activities (IC 50 < 5 μM).

[Additional file 1]

   Bisquinoline Derivatives Top

Antimalarial drug containing bisquinoline was first synthesized in the 1960s (piperaquine) and used extensively in China as a prophylactic and for treatment against malaria during that era. With the development of piperaquine-resistant strains of P. falciparum and the emergence of the artemisinin derivatives, its use declined during the 1980s. [13] Recently, various laboratories all over the world have again focused on developing potential antimalarial agents having bisquinoline structure. Ayad et al. [14] synthesized a series of novel bisquinoline compounds 6 comprising 4-(4-diethylamino-1-methylbutyl)aminoquinoline units joined through the 2-position by a (CH 2 )n linker and evaluated their ability to inhibit the growth of both CQ-sensitive (CQS) (D10) and CQR (K1) strains of P. falciparum, the hydrogen peroxide-mediated pathway for decomposition of heme and the conversion of heme to β-hematin. Results of the study revealed that the most active compound (n = 12) exhibited effects similar to CQ in three of the assays. However, it was even more active against the resistant strain [IC 50 , 17 nM (K1); 43 nM (D10)], much superior to CQ (IC 50 , 540 nM) and slightly better than mefloquine (IC 50 , 30 nM).

[Additional file 2]

A series of bisquinoline derivatives 7 have been synthesized and screened in vitro for methemoglobin (MetHb) formation and methemoglobin reductase activity by Srivastava et al., [15] with promising antimalarial activity. N,N-bis(7-chloroquinolin-4-yl)heteroalkanediamines 8 were synthesized and screened in vitro against P. falciparum and P. berghei in vivo by Vennerstrom et al. [16] These bisquinolines showed IC 50 values in the range of 1-100 nM against P. falciparum (in vitro) while they were potent inhibitors of hematin polymerization with IC 50 values falling in the narrow range of 5−20 μM.

[Additional file 3]

   Chloroquine Analogs Top

CQ, N'-(7-chloroquinolin-4-yl)-N,N-diethyl-pentane-1,4-diamine was discovered in 1934 by Hans Andersag and coworkers at the Bayer laboratories, who named it "Resochin". It was ignored for a decade because it was considered too toxic for human use. During World War II, the United States government-sponsored clinical trials for antimalarial drug development showed unequivocally that CQ has a significant therapeutic value as an antimalarial drug. It was introduced into clinical practice in 1947 for the prophylactic treatment of malaria. Until the emergence of CQR strains of P. falciparum, this drug was treated as panacea against the malaria disease. In the last few decades, there has been a tremendous amount of research activity directed toward the development of potent antimalarials based on chloroquine.

Faruk Khan et al. [17] reported a semirigid analog of the antimalarial drug CQ by incorporating isoquinuclidine (2-azabicyclo[2.2.2]octane) 9 , 10 ring system which may be viewed as a semirigid boat form of the piperidine ring and, when properly substituted, a scaffold for rigid analogs of biologically active ethanolamines and propanolamines. All the analogs were tested in vitro against P. falciparum strains and Leishmania donovani promastigote cultures and some of them displayed potent antimalarial activity against both CQ-susceptible D6 and the CQR W2 strains of P. falciparum. Similarly, Solomon et al. [18] reported a series of CQ analogs containing guanyl and tetramethylguanyl moieties 11 and tested in vitro against CQS strain of P. falciparum and CQR N-67 strain of P. yoelii in vivo. All the analogs were found to form strong complex with hematin and inhibit the β-hematin formation in vitro and this suggests that these compounds act on heme polymerization.

[Additional file 4]

They also synthesized a new series of side chain modified, i.e., 4-aminoquinolines 2-(substituted phenyl)-2,3-dihydro-4H-1,3-benzothiazin-4-one incorporated, CQ derivatives 12 with potent antimalarial activity against P. falciparum in vitro and P. yoelli in vivo.[19] A series of (trifluoromethyl-1H-pyrazol-1-yl) analogs incorporating CQ motif were designed and synthesized by Cunico et al. [20] and compound 13 showed significant activity in vitro and emerged to be a promising new class of antimalarial drug. The transformation of freely rotatable N,N-diethyl-pentane-1,4-diamine chain of CQ into semirigid structure using pyrrolizidinylalkyl 14 motif has been reported by Sparatore et al. [21] and tested in vitro against CQS and CQR strains of P. falciparum and in vivo in a P. berghei mouse model of infection. Both the compounds exhibited excellent activity in all tests and low toxicity against mammalian cells. Development of novel metal-based chemotherapeutic agent has become an area of interest against many tropical diseases. Navarro et al. [22] prepared a number of new Au(I) and Au(III) complexes of CQ 15 , 16 and evaluated them in vitro against several strains of P. falciparum. All the complexes displayed in vitro activity against CQS and CQR strains of P. falciparum. The highest activity for this series was obtained for complex Au(I), which is 5 times more active than chloroquine diphosphate (CQDP) against the CQR strain FcB1. Ray and coworkers designed two lead molecules, 17 and 18 , with promising in vitro therapeutic efficacy, improved Absorption Distribution Metabolism Excretion and Toxicity (ADMET) properties, low risk for drug−drug interactions, and desirable pharmacokinetic profiles. Both the derivatives exhibited highly potent antimalarial activity, with IC 50 values of 5.6 and 17.3 nM, respectively, against the W2 (CQR) strain of P. falciparum (for CQ, IC 50 = 382 nM). [23]

[Additional file 5]

Based on the fact that incorporation of an intermolecular hydrogen-bonding motif in the side chain of 4-aminoquinolines enhanced the activity against drug-resistant P. falciparum, a series of 116 compounds 19 , 20 containing four different alkyl linkers and various aromatic substitutions with hydrogen bond accepting capability were synthesized by Madrid et al. [24] Compounds showed broad potency against the drug-resistant W2 strain of P. falciparum and, in particular, a novel series containing variations of the a-aminocresol motif gave compounds with IC 50 values more potent than 5 nM against the W2 strain.

[Additional file 6]

Design and synthesis of antimalarials based on novel structural pharmacophores has become an important approach for developing potential antimalarial agent in recent times. Antimalarials based on a polyaromatic pharmacophore were designed by Gemma et al. [25],[26] using hybrid molecules with clotrimazole-like pharmacophore with a polyarylmethyl group 21 , 22 . These compounds were found to be selective in interacting with free heme and interfering with P. falciparum heme metabolism. The reason for this interaction appeared to be a combination of the polyarylmethyl system, which enables to form and stabilize radical intermediates, with the iron-complexing and conjugation-mediated electron transfer properties of the 4(9)-aminoquinoline(acridine). Among the compounds tested, 21 exhibited in vivo potent activity against P. chabaudi and P. berghei after oral administration and possessed promising pharmacokinetic properties. It was selected for further preclinical development. To overcome the development of resistance against CQ, a class of hybrid molecules, which we term "reversed chloroquines" (RCQs), 23 was designed by Burgess et al. [27] A prototype molecule, N'-(7-chloroquinolin-4-yl)-N-[3-(10,11-dihydrodibenzo[b,f]azepin-5-yl)propyl]-N-methylpropane-1,3-diamine 24 was found to be effective at low nanomolar concentrations against both CQS and CQR strains of P. falciparum.

[Additional file 7]

Combination of two pharmacophores in a single matrix with synergistic effect is one of the approaches in drug design for the development of potent bioactive molecules. 1, 2, 4-trioxane as an active motif of artemisinin, a naturally occurring potent antimalarial, has resulted in the development of newer class of synthetic peroxide-containing drugs as antimalarials. Opsenica et al. [28] have synthesized chimeric molecules consisting of two pharmacophores, tetraoxane and 7-chloro-4-aminoquinoline, and showed relatively potent in vitro antimalarial activities, with IC 90 values for the P. falciparum strain W2 in the range of 2.26-12.44 nM. Compound 25 exhibited potent in vivo activity in cured mice. Likewise, a series of hybrid molecules 2-[3-(7-chloro-quinolin-4-ylamino)-alkyl]-1-(substitutedphenyl)-2, 3, 4, 9-tetrahydro-1H-b-carbolines 26 have been synthesized by Gupta et al. [29] and screened for their in vitro antimalarial activity. Some of derivatives showed minimum inhibitory concentration MIC in the range of 0.05-0.11 μM and were several folds more active than CQ in vitro. A series of new 7-chloroquinolinyl thiourea 27 derivatives derived from the corresponding 4,7-dichloroquinoline isothiocyanate were prepared and evaluated for in vitro antimalarial and anticancer activity. The most active compound from the series displayed an inhibitory IC 50 value of 1.2 μM against the D10 strain of P. falciparum.[30]

[Additional file 8]

   Piperazine Incorporated Chloroquine Analogs Top

A variety of piperazine incorporated chloroquinie analogs have been designed and synthesized to improve its efficacy and its effectiveness against CQR strains. Flipo et al. [31] reported a new class of piperazine incorporated CQ analog as an inhibitor of PfA-M1, a neutral zinc aminopeptidase of P. falciparum, a new potential target for the discovery of new antimalarial agents, and compound 28 showed an IC 50 of 854 nM. Likewise, Ryckebusch et al. reported a series of N1 -(7-chloro-4-quinolyl)-1,4-bis(3-aminopropyl)piperazine derivatives 29 and evaluated their antimalarial activity against a CQR strain of P. falciparum.[32]

[Additional file 9]

A series of 4-aminoquinoline-containing 2, 4, 5-trisubstituted aminoxazoles 30 and piperazine/morpholine were synthesized and screened in vitro against two strains of the P. falciparum parasite by Musonda et al. A number of compounds exhibited significantly more potent activity than the standard drug CQ. [33]

[Additional file 10]

   Amodiaquine Analog Top

AQ is a 4-aminoquinoline, structurally related to CQ in which N,N-diethyl-pentane-1,4-diamine chain is replaced by 2-[(diethylamino)methyl]phenol and was found to be more effective against CQR parasites. But its use is compromised by its hepatotoxicity and its ability to cause agranulocytosis. Pharmacologic studies have revealed that a regioisomer of AQ, in which the positions of the groups on the hydroxyl aniline ring have been swapped, cannot be oxidized to the quinone imine and was comparatively less hepatotoxic. Further optimization led to the discovery of N-t-butyl-isoquine 31 , which is now being transitioned toward antimalarial clinical trials. [34],[35]

[Additional file 11] Casagrande et al. [36] designed a new class of antimalarial agents by replacing the phenolic ring of AQ, tebuquine, and isoquine with other aromatic nuclei and reported that several compounds containing pyrrole analogs 32 , 33 displayed high activity against both D10 (CQS) and W-2 (CQR) strains of P. falciparum. Similarly, Sandrine et al. [37] studied the significance of the 4′-phenolic group in the antimalarial activity and/or cytotoxicity of AQ and synthesized newer analogs of AQ in which the phenolic group was either shifted or modified. Among the compounds tested, new amino derivative 34 displayed the greatest selectivity index toward the most CQR strain and was active in mice infected by P. berghei. A series of new AQ derivatives bearing modified lateral basic chains as new agents 35 with both antimalarial and antileishmanial activities were reported by Guglielmo et al. Most of the compounds displayed antileishmanial activity in low micromolar range and were cytotoxic with a narrow therapeutic window. [38]

[Additional file 12]

   8-Aminoquinoline Analogs Top

8-aminoquinoline is another class of quinoline-based antimalarial drug that contains three members, primaquine, tafenoquine and pamaquine, which are used in the treatment of malaria. They may be used to eradicate malarial hypnozoites from the liver and have been used for malarial prophylaxis. Pamaquine is no longer available, but primaquine is still used routinely worldwide as a part of the treatment of P. vivax and P. ovale malaria. Tafenoquine is currently in Phase III clinical trials and is still not available for prescription.

[Additional file 13]

The structural exploitation of this class is still going on and numerous reports are available on recent developments based on this phrmacophore. Jain et al. [39] reported a series of 8-quinolinamines related to 2-tert-butylprimaquine and evaluated them for their in vitro antimalarial activity. Among the compound tested, analog 36 was found to exhibit curative antimalarial activity at a dose of 25 mg/kg/day Χ 4 in a P. berghei infected mice model, and produced suppressive activity at a lower dose of 10 mg/kg/day Χ 4. The research group further studied the antimalarial activity of amino acid, e.g., alanine, lysine, ornithine and valine conjugated to primaquine and other 8-quinolinamine 37 . The results of this study represent a development of highly potent 8-quinolinamine derivatives for antimalarial activity. Compound N1 -[4-(5-butoxy-4-ethyl-6-methoxy-8-quinolylamino)pentyl]-(2S)-2,6-diaminohexanamide that showed curative activity at 5 mg/kg in the P. berghei test emerged as the most effective compound and compound N1 -[4-(4-ethyl-5-hexoxy-6-methoxy-8-quinolylamino)pentyl]-(2S)-2,6-diaminohexanamide exhibited curative activity at 50 mg/kg against P. yoelii nigeriensis in mice and was found to be most potent analog against multidrug resistant strain. [40]

Imidazolidin-4-one derivatives of primaquine were synthesized as potential double prodrugs of the parent drug by Araϊjo et al. [41] and the derivatives were found to inhibit the development of the sporogonic cycle of P. berghei, affecting the appearance of oocysts in the midguts of the mosquitoes. These imidazolidin-4-one derivatives 38 of primaquine represent novel transmission-blocking antimalarials. To avoid the unwanted metabolic pathway of the quinoline ring of primaquine has results in development of new stearically hindered derivative of primaquine where C-2 position of drug is blocked by metabolically stable bulky alkyl group [R = C(CH 3 ) 3 ]. This compound 39 showed excellent antimalarial efficacy against P. berghei in vivo and was highly potent against multidrug resistant P. yoelii nigeriensis strain. This study describes the discovery of a highly potent blood-schizontocidal antimalarial analog 2 , completely devoid of MetHb toxicity. [42]

[Additional file 14]

[Additional file 15]

   Acridine and Quinoline Fused Analog Top

Quinacrine is an acridine-based antiprotozoal which has been used as an antimalarial agent. It is also used in other protozoal infections which include giardiasis, where quinacrine is indicated as a primary agent for patients with metronidazole-resistant giardiasis and for patients who should not receive or cannot tolerate metronidazole. Many useful structural modifications of acridine and its derivatives are in progress to generate potential antimalarial drugs based on this nucleus. Guetzoyan et al. [43] reported a series of acridine derivatives 40, 41 and their in vitro antimalarial activity evaluation against one CQ-susceptible strain (3D7) and three CQR strains (W2, Bre1 and FCR3) of P. falciparum. Structure activity relationship SAR of compounds showed that two positives charges as well as 6-chloro and 2-methoxy substituents on the acridine ring were required to exert a good antimalarial activity and compounds possessing these features inhibited the growth of the CQ-susceptible strain with an IC 50 ≤ 0.07 μM, close to that of CQ, and better than CQ against CQR strains with IC 50 ≤ 0.3 μM. Among them, compound 9-(6-ammonioethylamino)-6-chloro-2-methoxyacridinium dichloride displayed a promising antimalarial activity in vitro with a quite good selectivity index

versus mammalian cell on the CQ-susceptible strain and promising selectivity on other strains. A series of bis(9-amino-6-chloro-2-methoxyacridine) derivatives 42 in which acridine moieties were joined by alkanediamines, polyamines, or polyamines substituted by a side chain, were synthesized and tested for their antimalarial activity by Girault et al. [44] The results of the study revealed the importance of the nature of the linker and its side chain for antiparasitic activity, cytotoxicity, and cellular localization. Some of the compounds displayed IC 50 values ranging from 8 to 18 nM against different P. falciparum strains while three others totally inhibited Trypanosoma brucei at 1.56 μM.

[Additional file 16]

[Additional file 17]

In another study, a series N2-acrydinylhydrazones 43 were synthesized and tested for their antimalarial properties. These compounds showed remarkable in vitro anti-plasmodial activity, especially against CQR strains. [45] Joshi et al. designed and synthesized a series of novel 5-substituted amino-2,4-diamino-8-chloropyrimido- [4,5-b]quinolines 44 based on the pharmacophore developed for potent antimalarial activity, using Chem-X and MOE softwares. The compounds were evaluated by Rane's test for blood schizonticidal activity in mice infected by P. berghei. Based on the Mean Survival Time (MST) data of the nine compounds evaluated, three were found to have curative potential when compared with CQ. [46] On the basis of the original lead neocryptolepine or 5-methyl-5H-indolo [2,3-b]quinoline, an alkaloid from Cryptolepis sanguinolenta, derivatives were prepared using a biradical cyclization methodology and screened for their antimalarial activity and cytotoxicity on human MRC-5 cells. 2-Bromoneocryptolepine 45 was the most selective compound with an IC 50 value against CQR P. falciparum of 4.0 μM. 2-bromoneocryptolepine showed a low affinity for DNA and no inhibition of human topoisomerase II, in contrast to cryptolepine. [47]

[Additional file 18]

   Organometallic Ferrocene Analog of Quinoline Top

This is one of the recent approaches evolved for the design and development of newer potent derivatives for malarial chemotherapy. In these molecules, which are generally analogs of CQ, a ferrocene nucleus (dicyclopentadienyl iron) is localized at different sites of molecule and then evaluated for antimalarial activity. [48] Based on this approach, a new series of organic and organometallic dual drugs 46 were designed as potential antimalarial agents by Wenzel et al. [49] Several compounds not only showed a marked antimalarial activity with IC 50 and IC 90 values in the low nanomolar range, but also showed a high cytotoxicity against mammalian cells. The newly designed compounds revealed high DNA binding properties, especially for the GC-rich domains. Altogether, these dual drugs seem to be more appropriate to be developed as antiproliferative agents against mammalian cancer cells than Plasmodium parasites. Similarly, easily accessible ferrocenic quinoline derivatives were synthesized by Biot et al. [50] from triazacyclononane and were evaluated for their antiplasmodial properties against CQS (HB3) and CQR (Dd2) P. falciparum. Compound 7-chloro-4-[4-(7-chloro-4-quinolyl)-7-ferrocenylmethyl-1, 4, 7-triazacyclononan-1-yl]quinoline 47 showed potent antimalarial activity in vitro against the CQR strain Dd2. Dubar et al. [51] carried out the derivatization of the fluoroquinolone, ciprofloxacin, with a ferrocene nucleus (dicyclopentadienyl iron) resulting in new achiral compounds 48 which were found to be 10- to 100-fold more active than ciprofloxacin against P. falciparum CQ-susceptible and CQR strains. These achiral derivatives killed parasites more rapidly than ciprofloxacin. These derivatives appeared to be promising new leads and creating a new family of antimalarial agents.

[Additional file 19]

   References Top

1.WHO Expert Committee on Malaria. Technical Report Series. 20 th Report, Geneva: World Health Organization; 2000.   Back to cited text no. 1      
2.Snow RW, Guerra CA, Noor AM, Myint HY, Hay SI. The global distribution of clinical episodes of Plasmodium falciparum malaria. Nature 2005;434:214-7.  Back to cited text no. 2      
3.Bathurst I, Hentschel C, Medicines for Malaria Venture: Sustaining antimalarial drug development. Trends Parasitology 2006;22:301-7.   Back to cited text no. 3      
4.Gelb MG. Drug discovery for malaria: A very challenging and timely endeavor. Curr Opin Chem Biol 2007;11:440-5.   Back to cited text no. 4      
5.Rosenthal PJ. Antimalarial drug discovery: Old and new approaches. J Exp Biol 2003;206:3735-44.  Back to cited text no. 5      
6.Robert A, Benoit-Vical F, Dechy-Cabaret O, Meunier B. From classical antimalarial drugs to new compounds based on the mechanism of action of artemisinin. Pure Appl Chem 2001;73:1173-88.   Back to cited text no. 6      
7.Coslιdan F, Fraisse L, Pellet A, Guillou F, Mordmόller B, Kremsner PG, et al. Selection of a trioxaquine as an antimalarial drug candidate. Proc Natl Acad Sci U S A 2008;105:17579-84.  Back to cited text no. 7      
8.Chen M, Theander TG, Christensen BS, Hviid L, Zhai L, Kharazmi A. Licochalcone A, a new antimalarial agent, inhibits in vitro growth of the human malaria parasite Plasmodium falciparum and protects mice from P. yoelii infection. Antimicrob Agents Chemothe, 1994;38:1470-5.   Back to cited text no. 8      
9.Charris JE, Domνnguez JN, Gamboa N, Rodrigues JR, Angel JE. Synthesis and antimalarial activity of E-2-quinolinylbenzocycloalcanones. Eur J Med Chem 2005;40:875-81.   Back to cited text no. 9      
10.Domνnguez JN, Charris JE, Lobo G, Gamboa-Domνnguez N, Moreno MM, Riggione F, et al. Synthesis of quinolinyl chalcones and evaluation of their antimalarial activity. Eur J Med Chem 2001;36:555-60.   Back to cited text no. 10      
11.Charris JE, Lobo GM, Camacho J, Ferrer R, Barazarte A, Domνnguez JN, et al. Synthesis and Antimalarial Activity of (E) 2-(2΄-Chloro-3΄- Quinolinylmethyl idene)-5,7-Dimethoxyindanones. Lett Drug Des Discovery 2007;4:49-54.   Back to cited text no. 11      
12.Liu M, Wilairat P, Go M-L. Antimalarial Alkoxylated and Hydroxylated Chalones: Structure−Activity Relationship Analysis. J Med Chem 2001;44:4443-52.  Back to cited text no. 12      
13.Davis TM, Hung TY, Sim IK, Karunajeewa HA, Ilett KF. Piperaquine: A Resurgent Antimalarial Drug. Drugs 2005;65:75-87.  Back to cited text no. 13      
14.Ayad F, Tilley L, Deady LW. Synthesis, antimalarial activity and inhibition of haem detoxification of novel bisquinolines. Bioorg Med Chem 2001;11:2075-7.  Back to cited text no. 14      
15.Srivastava S, Tewari S, Chauhan PM, Puri SK, Bhaduri AP, Pandey VC. Synthesis of bisquinolines and their in vitro ability to produce methemoglobin in canine hemolysate. Bioorg Med Chem Lett 1999;09:653-8.  Back to cited text no. 15      
16.Vennerstrom JL, Jr Ager AL, Dorn A, Andersen SL, Gerena L, Ridley RG, et al. Bisquinolines. 2. Antimalarial N,N-Bis(7-chloroquinolin-4-yl)heteroalkanediamines. J Med Chem 1998;41:4360-4.  Back to cited text no. 16      
17.Faruk Khan MO, Levi MS, Tekwani BL, Wilson NH, Borne RG. Synthesis of isoquinuclidine analogues of chloroquinie: Antimalarial and antileishmanial activity. Bioorg Med Chem 2007;15:3919-25.  Back to cited text no. 17      
18.Solomon VR, Puri SK, Srivastava K, Katti SB. Design and synthesis of new antimalarial agents from 4-aminoquinoline. Bioorg Med Chem 2005;13:2157-65.  Back to cited text no. 18      
19.Solomon VR, Haq W, Srivastava K, Puri SK, Katti SB. Synthesis and Antimalarial Activity of Side Chain Modified 4-Aminoquinoline Derivatives. J Med Chem 2007;50:394-8.  Back to cited text no. 19      
20.Cunico W, Cechinel CA, Bonacorso HG, Martins MAP, Zanatta N, De Souza MV, et al. Antimalarial activity of 4-(5-trifluoromethyl-1H-pyrazol-1-yl)-chloroquine analogues. Bioorg Med Chem Lett 2006;16:649-53.  Back to cited text no. 20      
21.Sparatore A, Basilico N, Casagrande M, Parapini S, Taramelli D, Brun R, et al. Antimalarial activity of novel pyrrolizidinyl derivatives of 4-aminoquinoline. Bioorg Med Chem Lett 2008;18:3737-40.  Back to cited text no. 21      
22.Navarro M, Vαsquez S, Sαnchez-Delgado RA, Pιrez H, Sinou V, Schrιvel J. Toward a Novel Metal-Based Chemotherapy against Tropical Diseases. 7. Synthesis and in vitro Antimalarial Activity of New Gold−Chloroquine Complexes. J Med Chem 2004;47:5204-9.   Back to cited text no. 22      
23.Ray S, Madrid PB, Catz P, LeValley SE, Furniss MJ, Rausch LL, et al. Development of a New Generation of 4-Aminoquinoline Antimalarial Compounds Using Predictive Pharmacokinetic and Toxicology Models. J Med Chem 2010;53:3685-95.   Back to cited text no. 23      
24.Madrid PB, Liou AP, DeRisi JL, Guy KR. Incorporation of an Intramolecular Hydrogen-Bonding Motif in the Side Chain of 4-Aminoquinolines Enhances Activity against Drug-Resistant P. falciparum. J Med Chem 2006;49:4535-43.   Back to cited text no. 24      
25.Gemma S, Campiani G, Butini S, Joshi BP, Kukreja G, Coccone SS, et al Combining 4-Aminoquinoline- and Clotrimazole-Based Pharmacophores toward Innovative and Potent Hybrid Antimalarials. J Med Chem 2009;52:502-13.  Back to cited text no. 25      
26.Gemma S, Campiani G, Butini S, Joshi BP, Kukreja G, Coccone SS, et al. Clotrimazole Scaffold as an Innovative Pharmacophore Towards Potent Antimalarial Agents: Design, Synthesis, and Biological and Structure-Activity Relationship Studies. J Med Chem 2008;51:1278-94.   Back to cited text no. 26      
27.Burgess SJ, Selzer A, Kelly JX, Smilkstein MJ, Riscoe MK, Peyton DH. A Chloroquine-like Molecule Designed to Reverse Resistance in Plasmodium falciparum. J Med Chem 2006;49:5623-5.  Back to cited text no. 27      
28.Opsenica I, Opsenica D, Lanteri CA, Anova L, Milhous WK, Smith KS, et al. New Chimeric Antimalarials with 4-Aminoquinoline Moiety Linked to a Tetraoxane Skeleton. J Med Chem 2008;51:6216-9.   Back to cited text no. 28      
29.Gupta L, Srivastava K, Singh S, Puri SK, Chauhan PMS. Synthesis of 2-[3-(7-Chloro-quinolin-4-ylamino)-alkyl]-1-(substituted phenyl)-2,3,4,9-tetrahydro-1H-b-carbolines as a new class of antimalarial agents. Bioorg. Med. Chem. Lett., 2008; 18: 3306-3309.  Back to cited text no. 29      
30.Mahajan A, Yeh S, Nell M, Van Rensburg CE, Chibale K. Synthesis of new 7-chloroquinolinyl thiourea and their biological investigation as potential antimalarial and anticancer agents. Bioorg Med Chem Lett 2007;17:5683-5.  Back to cited text no. 30      
31.Flipo M, Florent I, Grellier P, Sergheraert C, Deprez-Poulain R. Design, synthesis and antimalarial activity of novel, quinoline-based, zinc metallo-aminopeptidase inhibitor. Bioorg Med Chem Lett 2003;13:2659-62.  Back to cited text no. 31      
32.Ryckebusch A, Debreu-Fontaine M-A, Mouray E, Grellier P, Sergheraert C, Melnyk P. Synthesis and antimalarial evaluation of N1 -(7-chloro-4-quinolyl)-1,4-bis(3-aminopropyl) Piperazine derivatives. Bioorg Med Chem Lett 2005;15:297-302.   Back to cited text no. 32      
33.Musonda CC, Little S, Yardley V, Chibale K. Application of multicomponant reaction to antimalarial drug discovery. Part 3: Discovery of aminoxazole 4-aminoquinolines with potent antiplasmodial activity in vitro. Bioorg Med Chem Lett 2007;17:4733-6.   Back to cited text no. 33      
34.O'Neill PM, Park BK, Shone AE, Maggs JL, Roberts P, Stocks PA, et al. Candidate Selection and Preclinical Evaluation of N-tert-Butyl Isoquine (GSK369796), An Affordable and Effective 4-Aminoquinoline Antimalarial for the 21 st Century. J Med Chem 2009;52:1408-15.   Back to cited text no. 34      
35.O'Neill PM, Mukhtar A, Stocks PA, Randle LE, Hindley S, Ward SA, et al. Isoquine and Related Amodiaquine Analogues: A New Generation of Improved 4-Aminoquinoline Antimalarials. J Med Chem 2003;46:4933-45.  Back to cited text no. 35      
36.Casagrande M, Basilico N, Parapini S, Romeo S, Taramelli D, Sparatore A. Novel amodiaquine congeners as potent antimalarial agent. Bioorg Med Chem 2008;16:6813-23.  Back to cited text no. 36      
37.Sandrine D-C, Paunescu E, Maes L, Mouray E, Sergheraert C, Grellier p, et al. Synthesis and antimalarial activity of new analogues of amodiaquine. Eur J Med Chem 2008;43:252-60.  Back to cited text no. 37      
38.Guglielmo S, Bertinaria M, Rolando B, Crosetti M, Fruttero R, Yardley V, et al. A new series of amodiaquine analogues modified in the basic side chain with in vitro antileishmanial and antiplasmodial activity. Eur J Med Chem 2009;44:5071-9.  Back to cited text no. 38      
39.Jain M, Khan SI, Tekwani BL, Jacob MR, Singh S, Jain R, et al. Synthesis, antimalarial, antileishmanial and antimicrobial activities of some 8-quinolinamine analogues. Bioorg Med Chem 2005;13:4458-66.  Back to cited text no. 39      
40.Vangapandu S, Sachdeva S, Jain M, Singh S, Singh PP, Jain R, et al. Quinolinamine conjugated with amino acids are exhibiting potent blood-schizontocidal antimalarial activities. Bioorg Med Chem 2004;12:239-47.   Back to cited text no. 40      
41.Araϊjo MJ, Bom J, Capela R, Casimiro C, Chambel P, Gomes P, et al. Imidazolidin-4-one Derivatives of Primaquine as Novel Transmission-Blocking Antimalarials. J Med Chem 2005;48:888-92.  Back to cited text no. 41      
42.Jain M, Vangapandu S, Sachdeva S, Singh S, Singh PP, Jena GB, et al. Discovery of a Bulky 2-tert-Butyl Group Containing Primaquine Analogue That Exhibits Potent Blood-Schizontocidal Antimalarial Activities and Complete Elimination of Methemoglobin Toxicity. J Med Chem 2004;47:285-7.  Back to cited text no. 42      
43.Guetzoyan L, Yu X-M, Ramiandrasoa F, Pethe S, Rogier C, Pradines B, et al. Antimalarial acridines: Synthesis, in vitro activity against P. falciparum and interaction with hematin. Bioorg Med Chem 2009;17:8032-9.   Back to cited text no. 43      
44.Girault S, Grellier P, Berecibar A, Maes L, Mouray E, Lemiθre P, et al. Antimalarial, Antitrypanosomal, and Antileishmanial Activities and Cytotoxicity of Bis(9-amino-6-chloro-2-methoxyacridines): Influence of the Linker. J Med Chem 2000;43:2646-54.   Back to cited text no. 44      
45.Gemma S, Kukreja G, Fattorusso C, Persico M, Romano MP, Altarelli M, et al. Synthesis of N1-arylidene-N2-quinolyl- and N2-acridinylhydrazones as potent antimalarial agents active against CQ-resistant P. falciparum strains. Bioorg Med Chem Lett 2006;16:5384-8   Back to cited text no. 45      
46.Joshi AA, Narkhede SS, Viswanathan CL. Design, synthesis and evaluation of 5-substituted amino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines as novel antimalarials. Bioorg Med Chem Lett 2005;15:73-6.   Back to cited text no. 46      
47.Jonckers TH, Miert S, Cimanga K, Bailly C, Colson P, De Pauw-Gillet M-C, et al. Synthesis, Cytotoxicity, and Antiplasmodial and Antitrypanosomal Activity of New Neocryptolepine Derivatives. J Med Chem 2002;45:3497-508.  Back to cited text no. 47      
48.Domarle O, Blampain G, Agnaniet H, Nzadiyabi T, Lebibi J, Brocard J, et al. In vitro Antimalarial Activity of a New Organometallic Analog, Ferrocene-Chloroquine. Antimicrob Agents Chemother 1998;42:540-4.   Back to cited text no. 48      
49.Wenzel NI, Chavain N, Wang Y, Friebolin W, Maes L, Pradines B, et al. Antimalarial versus Cytotoxic Properties of Dual Drugs Derived From 4-Aminoquinolines and Mannich Bases: Interaction with DNA. J Med Chem 2010;53:3214-26.  Back to cited text no. 49      
50.Biot C, Dessolin J, Ricard I, Dive D. Easily synthesized antimalarial ferrocene triazacyclononane quinoline conjugates. J Organomet Chem 2004;689:4678-82.   Back to cited text no. 50      
51.Dubar F, Anquetin G, Pradines B, Dive D, Khalife J, Biot C. Enhancement of the Antimalarial Activity of Ciprofloxacin Using a Double Prodrug/Bioorganometallic Approach. J Med Chem 2009;52:7954-7.  Back to cited text no. 51      


  [Figure 1]

This article has been cited by
1 A study of structure–activity relationship and anion-controlled quinolinyl Ag(I) complexes as antimicrobial and antioxidant agents as well as their interaction with macromolecules
Adesola A. Adeleke, Sizwe J. Zamisa, Md. Shahidul Islam, Kolawole Olofinsan, Veronica F. Salau, Chunderika Mocktar, Bernard Omondi
BioMetals. 2022;
[Pubmed] | [DOI]
2 Punica granatum pericarp extract catalyzed green chemistry approach for synthesizing novel ligand and its metal(II) complexes: Molecular docking/DNA interactions
G.T. Vidyavathi, B. Vinay Kumar, Anjanapura V. Raghu, T. Aravinda, U. Hani, H.C. Ananda Murthy, A.H. Shridhar
Journal of Molecular Structure. 2022; 1249: 131656
[Pubmed] | [DOI]
3 Spectroscopic investigations, DFT calculations, molecular docking and MD simulations of 3-[(4-Carboxyphenyl) carbamoyl]-4-hydroxy-2-oxo-1, 2-dihydroxy quinoline-6-carboxylic acid
P.K. Ranjith, Angel Ignatious, C. Yohannan Panicker, B. Sureshkumar, Stevan Armakovic, Sanja J. Armakovic, C. Van Alsenoy, P.L. Anto
Journal of Molecular Structure. 2022; : 133315
[Pubmed] | [DOI]
4 A review on synthetic investigation for quinoline- recent green approaches
Ashish Patel, Stuti Patel, Meshwa Mehta, Yug Patel, Rushi Patel, Drashti Shah, Darshini Patel, Umang Shah, Mehul Patel, Swayamprakash Patel, Nilay Solanki, Tushar Bambharoliya, Sandip Patel, Afzal Nagani, Harnisha Patel, Jitendra Vaghasiya, Hirak Shah, Bijal Prajapati, Mrudangsinh Rathod, Bhargav Bhimani, Riddhisiddhi Patel, Vashisth Bhavsar, Brijesh Rakholiya, Maitri Patel, Prexa Patel
Green Chemistry Letters and Reviews. 2022; 15(2): 336
[Pubmed] | [DOI]
5 Synthesis and Cytotoxicity Screening of Some Synthesized Coumarin and Aza-Coumarin Derivatives as Anticancer Agents
Ibrahim M. El-Deen, Manar A. El-Zend, Mohamed A. Tantawy, Lamiaa A. A. Barakat
Russian Journal of Bioorganic Chemistry. 2022; 48(2): 380
[Pubmed] | [DOI]
6 Styrylquinolines Derivatives: SAR Study and Synthetic Approaches
Monika Saini, Rina Das, Dinesh Kumar Mehta, Samrat Chauhan
Medicinal Chemistry. 2022; 18(8): 859
[Pubmed] | [DOI]
7 A Review of Modifications of Quinoline Antimalarials: Mefloquine and (hydroxy)Chloroquine
Dawid J. Kucharski, Michalina K. Jaszczak, Przemyslaw J. Boratynski
Molecules. 2022; 27(3): 1003
[Pubmed] | [DOI]
8 Domino Nitro Reduction-Friedländer Heterocyclization for the Preparation of Quinolines
Kwabena Fobi, Richard A. Bunce
Molecules. 2022; 27(13): 4123
[Pubmed] | [DOI]
9 Computational Study on Molecular Structure, UV-Visible and Vibrational Spectra and Frontier Molecular Orbital Analysis of (E)-7-((2-Chloroquinolin-3-yl)methylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one
Vishnu A. Adole, Abhijit R. Bukane, Ravindra H. Waghchaure, Rohit S. Shinde, Bapu S. Jagdale
Research Journal of Pharmacy and Technology. 2022; : 1101
[Pubmed] | [DOI]
10 In silico Analysis of Novel Azetidinone substituted benzotriazole and benzimidazole derivatives as Plasmodium falciparum Glutamate Dehydrogenase Inhibitors
Sandip N. Badeliya, Pankaj P. Kapupara, Ankit B. Chaudhary
Research Journal of Pharmacy and Technology. 2022; : 1431
[Pubmed] | [DOI]
11 Identification of Drug Candidates for Breast Cancer Therapy Through Scaffold Repurposing: A Brief Review
Jubie Selvaraj, Thangavelu Prabha, Neetu Yadav
Current Drug Research Reviews. 2021; 13(1): 3
[Pubmed] | [DOI]
12 Eco-Friendly Synthesis, Biological Evaluation, and In Silico Molecular Docking Approach of Some New Quinoline Derivatives as Potential Antioxidant and Antibacterial Agents
Ahmed M. El-Saghier, Mohamed El-Naggar, Abdel Haleem M. Hussein, Abu-Bakr A. El-Adasy, M. Olish, Aboubakr H. Abdelmonsef
Frontiers in Chemistry. 2021; 9
[Pubmed] | [DOI]
13 Quinoline Antimalarials Increase the Antibacterial Activity of Ampicillin
Olajumoke A. Olateju, Chinedum P. Babalola, Olujide O. Olubiyi, Olayinka A. Kotila, David A. Kwasi, Anderson O. Oaikhena, Iruka N. Okeke
Frontiers in Microbiology. 2021; 12
[Pubmed] | [DOI]
14 An Overview of the Medicinally Important Plant Type III PKS Derived Polyketides
Renu Bisht, Aniket Bhattacharyya, Ankita Shrivastava, Priti Saxena
Frontiers in Plant Science. 2021; 12
[Pubmed] | [DOI]
15 Hybrid Quinoline-Thiosemicarbazone Therapeutics as a New Treatment Opportunity for Alzheimer’s Disease?Synthesis, In Vitro Cholinesterase Inhibitory Potential and Computational Modeling Analysis
Sumera Zaib, Rubina Munir, Muhammad Tayyab Younas, Naghmana Kausar, Aliya Ibrar, Sehar Aqsa, Noorma Shahid, Tahira Tasneem Asif, Hashem O. Alsaab, Imtiaz Khan
Molecules. 2021; 26(21): 6573
[Pubmed] | [DOI]
16 Synthesis and Antimalarial Activity of 4-Methylaminoquinoline Compounds against Drug-Resistant Parasite
Vinay Shankar Tiwari, Prince Joshi, Kanchan Yadav, Anamika Sharma, Sushobhan Chowdhury, Ashan Manhas, Niti Kumar, Renu Tripathi, Wahajul Haq
ACS Omega. 2021; 6(20): 12984
[Pubmed] | [DOI]
17 The antimicrobial potential and pharmacokinetic profiles of novel quinoline-based scaffolds: synthesis and in silico mechanistic studies as dual DNA gyrase and DHFR inhibitors
Mohamed H. El-Shershaby, Kamal M. El-Gamal, Ashraf H. Bayoumi, Khaled El-Adl, Mohamed Alswah, Hany E. A. Ahmed, Ahmed A. Al-Karmalamy, Hamada S. Abulkhair
New Journal of Chemistry. 2021; 45(31): 13986
[Pubmed] | [DOI]
18 A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines
Santanu Ghora, Chinnabattigalla Sreenivasulu, Gedu Satyanarayana
Synthesis. 2021;
[Pubmed] | [DOI]
19 Site-Selective C8-Alkylation of Quinoline N-Oxides with Maleimides under Rh(III) Catalysis
Won An, Suk Hun Lee, Dayoung Kim, Harin Oh, Suho Kim, Youjung Byun, Hyun Jin Kim, Neeraj Kumar Mishra, In Su Kim
The Journal of Organic Chemistry. 2021; 86(11): 7579
[Pubmed] | [DOI]
20 Copper-Catalyzed Formal [3 + 3] Annulations of Arylketoximes and o-Fluorobenzaldehydes: An Entry to Quinoline Compounds
Zhenhua Xu, Hongbiao Chen, Guo-Jun Deng, Huawen Huang
Organic Letters. 2021; 23(3): 936
[Pubmed] | [DOI]
21 Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents
Fostino R.B. Bokosi, Richard M. Beteck, Mziyanda Mbaba, Thanduxolo E. Mtshare, Dustin Laming, Heinrich C. Hoppe, Setshaba D. Khanye
Bioorganic & Medicinal Chemistry Letters. 2021; 38: 127855
[Pubmed] | [DOI]
22 An efficient excited-state proton transfer fluorescence quenching based probe (7-hydroxyquinoline) for sensing trivalent cations in aqueous environment
Mohan Singh Mehata
Journal of Molecular Liquids. 2021; 326: 115379
[Pubmed] | [DOI]
23 Exploration of Anti-plasmodial Activity of Prunus cerasoides Buch.-Ham. ex D. Don (family: Rosaceae) and Its Wood Chromatographic Fractions
Cheryl Sachdeva, Sandeep Kumar, Naveen K. Kaushik
Acta Parasitologica. 2021; 66(1): 205
[Pubmed] | [DOI]
24 Quinolinyl-pyrazoles: synthesis and pharmacological evolution in the recent decennial
Vrushabendra Basavanna, Srikantamurthy Ningaiah, Manasa Chandramouli, Anjali Sobha, Shridevi Doddamani
Journal of the Iranian Chemical Society. 2021; 18(7): 1479
[Pubmed] | [DOI]
25 Quinoline Derivative Enhances Human Sperm Motility and Improves the Functional Competence
Sandhya Kumari, Sujith Raj Salian, Arpitha Rao, Shilpa M. Somagond, Ravindra R. Kamble, Aravind Nesaragi, Jyotirekha Das, G. K. Rajanikant, Srinivas Mutalik, Shamprasad Varija Raghu, Satish Kumar Adiga, Guruprasad Kalthur
Reproductive Sciences. 2021; 28(5): 1316
[Pubmed] | [DOI]
26 Microwave prompted solvent-free synthesis of new series of heterocyclic tagged 7-arylidene indanone hybrids and their computational, antifungal, antioxidant, and cytotoxicity study
Vishnu A. Adole, Rahul A. More, Bapu S. Jagdale, Thansing B. Pawar, Santosh S. Chobe, Rahul A. Shinde, Sunil L. Dhonnar, Prashant B. Koli, Arun V. Patil, Abhijit R. Bukane, Rajesh N. Gacche
Bioorganic Chemistry. 2021; 115: 105259
[Pubmed] | [DOI]
27 Synthesis, antimicrobial evaluation, DNA gyrase inhibition, and in silico pharmacokinetic studies of novel quinoline derivatives
Mohamed H. El-Shershaby, Kamal M. El-Gamal, Ashraf H. Bayoumi, Khaled El-Adl, Hany E. A. Ahmed, Hamada S. Abulkhair
Archiv der Pharmazie. 2021; 354(2): 2000277
[Pubmed] | [DOI]
28 Activity prediction of aminoquinoline drugs based on deep learning
Wenle Wang, Jinquan Chen, Yujie Zhu, Feng Feng
Biotechnology and Applied Biochemistry. 2021; 68(4): 927
[Pubmed] | [DOI]
29 Straightforward Construction and Functionalizations of Nitrogen-Containing Heterocycles Through Migratory Insertion of Metal-Carbenes/Nitrenes
Satabdi Bera, Aniruddha Biswas, Rajarshi Samanta
The Chemical Record. 2021;
[Pubmed] | [DOI]
30 Synthesis and in silico ADME/Tox profiling studies of heterocyclic hybrids based on chloroquine scaffolds with potential antimalarial activity
Hegira Ramírez, Esteban Fernandez-Moreira, Juan R. Rodrigues, Michael R. Mijares, Jorge E. Ángel, Jaime E. Charris
Parasitology Research. 2021;
[Pubmed] | [DOI]
31 Synthesis and biological activities of nitro-hydroxy-phenylquinolines; validation of antibiotics effect over DNA gyrase inhibition and antimicrobial activity
J D. Bilavendran, Alagumuthu Manikandan, Ponnusamy Thangarasu, K Sivakumar
Journal of Heterocyclic Chemistry. 2020; 57(3): 1143
[Pubmed] | [DOI]
32 Synthesis and Antibacterial Activity of New N-Substituted Hexahydroquinolinone Derivatives and X-Ray Crystallographic Studies
Nangagoundan Vinoth, Chinnasamy Kalaiarasi, Poomani Kumaradhas, Pullar Vadivel, Appaswami Lalitha
ChemistrySelect. 2020; 5(9): 2696
[Pubmed] | [DOI]
33 Graphene Oxide Catalyzed One-pot Synthesis of Pyrimido[4,5-b]quinolinone-2,4-diones and their Biological Evaluation
Rabindranath Singha, Puja Basak, Malay Bhattacharya, Pranab Ghosh
ChemistrySelect. 2020; 5(21): 6514
[Pubmed] | [DOI]
34 Rhodium-Catalyzed Selective C-H Bond Functionalization of Quinolines
Ankit K. Dhiman, Ankita Thakur, Rakesh Kumar, Upendra Sharma
Asian Journal of Organic Chemistry. 2020; 9(10): 1502
[Pubmed] | [DOI]
35 Synthesis of 1,8-dioxooctahydroxanthene derivatives using ionic liquids, quantum chemical studies and anticancer activity
Reetu Sangwan, Monika Saini, Ruchi Verma, Saurabh Kumar, Monisha Banerjee, Sudha Jain
Journal of Molecular Structure. 2020; 1208: 127786
[Pubmed] | [DOI]
36 Advancements in the synthesis of fused tetracyclic quinoline derivatives
Ramadan A. Mekheimer, Mariam A. Al-Sheikh, Hanadi Y. Medrasi, Kamal U. Sadek
RSC Advances. 2020; 10(34): 19867
[Pubmed] | [DOI]
37 Solvent-free grindstone synthesis of four new (E)-7-(arylidene)-indanones and their structural, spectroscopic and quantum chemical study: a comprehensive theoretical and experimental exploration
Vishnu A. Adole, Ravindra H. Waghchaure, Sandip S. Pathade, Manohar R. Patil, Thansing B. Pawar, Bapu S. Jagdale
Molecular Simulation. 2020; 46(14): 1045
[Pubmed] | [DOI]
38 Novel Quinazolin-2,4-Dione Hybrid Molecules as Possible Inhibitors Against Malaria: Synthesis and in silico Molecular Docking Studies
Aboubakr Haredi Abdelmonsef, Mahmoud Eldeeb Mohamed, Mohamed El-Naggar, Hussain Temairk, Ahmed Mohamed Mosallam
Frontiers in Molecular Biosciences. 2020; 7
[Pubmed] | [DOI]
39 Mesoporous Aluminosilicates in the Synthesis of N-Heterocyclic Compounds
N. G. Grigor’eva, M. R. Agliullin, S. A. Kostyleva, S. V. Bubennov, V. R. Bikbaeva, A. R. Gataulin, N. A. Filippova, B. I. Kutepov, Nama Narender
Kinetics and Catalysis. 2019; 60(6): 733
[Pubmed] | [DOI]
40 Catalyst and Additive-Free Diastereoselective 1,3-Dipolar Cycloaddition of Quinolinium Imides with Olefins, Maleimides, and Benzynes: Direct Access to Fused N,N'-Heterocycles with Promising Activity against a Drug-Resistant Malaria Parasite
Rakesh Kumar, Sandeep Chaudhary, Rohit Kumar, Pooja Upadhyay, Dinkar Sahal, Upendra Sharma
The Journal of Organic Chemistry. 2018; 83(19): 11552
[Pubmed] | [DOI]
41 Preparation and nanoformulation of new quinolone scaffold-based anticancer agents: Enhancing solubility for better cellular delivery
Nehal H. Elghazawy,Amr Hefnawy,Nada K. Sedky,Ibrahim M. El-Sherbiny,Reem K. Arafa
European Journal of Pharmaceutical Sciences. 2017; 105: 203
[Pubmed] | [DOI]
42 Convenient synthesis, antimicrobial evaluation and molecular modeling of some novel quinoline derivatives
Wafaa S. Hamama,Mona E. Ibrahim,Aya A. Gooda,Hanafi H. Zoorob
Synthetic Communications. 2017; 47(3): 224
[Pubmed] | [DOI]
43 Synthesis of 4-azo-butenolides
Ana Paula da Rocha Pissurno,Rosangela da Silva de Laurentiz
Synthetic Communications. 2017;
[Pubmed] | [DOI]
44 L-Proline catalyzed three component synthesis of pyrano[2,3-c]pyrazole-5-carbonitrile derivatives and in vitro antimalarial evaluation
Kailasam Saravana Mani,Subramaniam Parameshwaran Rajendran
Synthetic Communications. 2017;
[Pubmed] | [DOI]
45 Aryl-alkyl-lysines: small molecular membrane-active antiplasmodial agents
Chandradhish Ghosh,Shweta Chaubey,Utpal Tatu,Jayanta Haldar
Med. Chem. Commun.. 2017;
[Pubmed] | [DOI]
46 A highly selective and sensitive fluorescent chemosensor for Zn2+ based on a diarylethene derivative
Erting Feng,Yayi Tu,Congbin Fan,Gang Liu,Shouzhi Pu
RSC Adv.. 2017; 7(79): 50188
[Pubmed] | [DOI]
47 Catalyst and solvent-free alkylation of quinoline N-oxides with olefins: A direct access to quinoline-substituted a-hydroxy carboxylic derivatives
Rakesh Kumar,Inder Kumar,Ritika Sharma,Upendra Sharma
Org. Biomol. Chem.. 2016; 14(9): 2613
[Pubmed] | [DOI]
48 Experimental and theoretical study of hydroxyquinolines: hydroxyl group position dependent dipole moment and charge-separation in the photoexcited state leading to fluorescence
Mohan Singh Mehata,Ajay K Singh,Ravindra Kumar Sinha
Methods and Applications in Fluorescence. 2016; 4(4): 045004
[Pubmed] | [DOI]
49 Convergent Synthesis of 2-Aryl-Substituted Quinolines by Gold-Catalyzed Cascade Reaction
Hirofumi Ueda,Minami Yamaguchi,Hidetoshi Tokuyama
[Pubmed] | [DOI]
50 One-pot synthesis of quinoline derivatives using choline chloride/tin (II) chloride deep eutectic solvent as a green catalyst
Dana Shahabi,Hossein Tavakol
Journal of Molecular Liquids. 2016; 220: 324
[Pubmed] | [DOI]
51 Nano KF/Clinoptilolite: An Effective Heterogeneous Base Nanocatalyst for Synthesis of Substituted Quinolines in Water
Hadi Sajjadi-Ghotbabadi,Shahrzad Javanshir,Faramarz Rostami-Charati
Catalysis Letters. 2016; 146(2): 338
[Pubmed] | [DOI]
52 Synthesis and Biological Evaluation of Ferrocenylquinoline as a Potential Antileishmanial Agent
Md Yousuf,Debarati Mukherjee,Abhishek Pal,Somaditya Dey,Supratim Mandal,Chiranjib Pal,Susanta Adhikari
ChemMedChem. 2015; 10(3): 546
[Pubmed] | [DOI]
53 Synthesis and Antiplasmodial Activity of Novel Chloroquine Analogues with Bulky Basic Side Chains
Bruno Tasso,Federica Novelli,Michele Tonelli,Anna Barteselli,Nicoletta Basilico,Silvia Parapini,Donatella Taramelli,Anna Sparatore,Fabio Sparatore
ChemMedChem. 2015; 10(9): 1570
[Pubmed] | [DOI]
54 A review on anticancer potential of bioactive heterocycle quinoline
Obaid Afzal,Suresh Kumar,Md Rafi Haider,Md Rahmat Ali,Rajiv Kumar,Manu Jaggi,Sandhya Bawa
European Journal of Medicinal Chemistry. 2015; 97: 871
[Pubmed] | [DOI]
55 Synthesis, spectral analysis (FT-IR, 1H NMR, 13C NMR and UV–visible) and quantum chemical studies on molecular geometry, NBO, NLO, chemical reactivity and thermodynamic properties of novel 2-amino-4-(4-(dimethylamino)phenyl)-5-oxo-6-phenyl-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile
Shaheen Fatma,Abha Bishnoi,Anil Kumar Verma
Journal of Molecular Structure. 2015; 1095: 112
[Pubmed] | [DOI]
56 Synthesis of 3-Sulfonylamino Quinolines from 1-(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion
Yalla Kiran Kumar,Gadi Ranjith Kumar,Thota Jagadeshwar Reddy,Balasubramanian Sridhar,Maddi Sridhar Reddy
Organic Letters. 2015; 17(9): 2226
[Pubmed] | [DOI]
57 Vibrational spectroscopic investigation (FT-IR and FT-Raman) using ab initio (HF) and DFT (B3LYP) calculations of 3-ethoxymethyl-1,4-dihydroquinolin-4-one
Jamelah S. Al-Otaibi,Reem I. Al-Wabli
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2015; 137: 7
[Pubmed] | [DOI]
58 Groove binding mediated structural modulation and DNA cleavage by quinoline appended chalcone derivative
Himank Kumar,Vinod Devaraji,Rangaraj Prasath,Manojkumar Jadhao,Ritika Joshi,Purushothaman Bhavana,Sujit Kumar Ghosh
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2015; 151: 605
[Pubmed] | [DOI]
59 Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine
Gordana Tasic,Veselin Maslak,Suren Husinec,Nina Todorovic,Vladimir Savic
Tetrahedron Letters. 2015; 56(19): 2529
[Pubmed] | [DOI]
60 Metal-free domino one-pot protocols for quinoline synthesis
Jaideep B. Bharate,Ram A. Vishwakarma,Sandip B. Bharate
RSC Adv.. 2015; 5(52): 42020
[Pubmed] | [DOI]
61 Recent advances in the synthesis of quinolines: a review
Shraddha M. Prajapati,Kinjal D. Patel,Rajesh H. Vekariya,Shyamali N. Panchal,Hitesh D. Patel
RSC Advances. 2014; 4(47): 24463
[Pubmed] | [DOI]
62 Potential anti-bacterial agents: montmorillonite clay-catalyzed synthesis of novel 2-(3,5-substituted-1H-pyrazol-1-yl)-3-substituted quinolines and their in silico molecular docking studies
Pasupala Pavan,R. Subashini,K. R. Ethiraj,Fazlur-Rahman Nawaz Khan
RSC Adv.. 2014; 4(101): 58011
[Pubmed] | [DOI]
63 Synthesis and Antitubercular Screening of [(2-Chloroquinolin-3-yl)methyl] Thiocarbamide Derivatives
Suresh Kumar,Neeraj Upmanyu,Obaid Afzal,Sandhya Bawa
Chemical Biology & Drug Design. 2014; 84(5): 522
[Pubmed] | [DOI]
64 The development and validation of an LC-MS/MS method for the determination of a new anti-malarial compound (TK900D) in human whole blood and its application to pharmacokinetic studies in mice
Efrem T Abay, Jan H van der Westhuizen, Kenneth J Swart, Liezl Gibhard, Matshawandile Tukulula, Kelly Chibale, Lubbe Wiesner
Malaria Journal. 2014; 13(1)
[Pubmed] | [DOI]
65 Synthesis of chiral chloroquine and its analogues as antimalarial agents
Manish Sinha,Vasanth R. Dola,Awakash Soni,Pooja Agarwal,Kumkum Srivastava,Wahajul Haq,Sunil K. Puri,Seturam B. Katti
Bioorganic & Medicinal Chemistry. 2014;
[Pubmed] | [DOI]
66 Synthesis and evaluation of new diaryl ether and quinoline hybrids as potential antiplasmodial and antimicrobial agents
Amita Mishra,Harikrishna Batchu,Kumkum Srivastava,Pratiksha Singh,Pravin K. Shukla,Sanjay Batra
Bioorganic & Medicinal Chemistry Letters. 2014; 24(7): 1719
[Pubmed] | [DOI]
67 Synthesis, characterization and antimalarial activity of quinoline–pyrimidine hybrids
Stefan I. Pretorius,Wilma J. Breytenbach,Carmen de Kock,Peter J. Smith,David D. N’Da
Bioorganic & Medicinal Chemistry. 2013; 21(1): 269
[Pubmed] | [DOI]
68 Synthesis of Alkyl and Aryl Substituted Benzo[h]Naphtho[1,2-b][1,6]naphthyridines
K. Prabha,K. J. Rajendra Prasad
Synthetic Communications. 2012; 42(15): 2277
[Pubmed] | [DOI]


    Similar in PUBMED
   Search Pubmed for
   Search in Google Scholar for
 Related articles
    Access Statistics
    Email Alert *
    Add to My List *
* Registration required (free)  

  In this article
    Quinoline Chalcones
    Bisquinoline Der...
    Chloroquine Analogs
    Piperazine Incor...
    Amodiaquine Analog
    Acridine and Qui...
    Organometallic F...
    Article Figures

 Article Access Statistics
    PDF Downloaded858    
    Comments [Add]    
    Cited by others 68    

Recommend this journal