Abstract
Among heterocyclic compounds, quinoline is one of the best ubiquitous heterocyclic rings for medicinal chemistry purposes. Quinoline appears to be a powerful chemical structure to develop new drug entities. The quinoline derivatives own a wide array of biological activities such as anticancer, antimalarial, antimicrobial, anti-inflammatory, anti-leishmanial, etc. Because of the wide spectrum of bioactivities, the scientific communities are still looking for more efficient synthetic routes to form quinoline derivatives. Therefore, the primary focus of this review is to provide a thorough and inclusive, updated report on quinoline analogs that may pave the way for more efficient drug development.
Keywords: Quinoline, Synthesis, Anti-inflammatory, Anticancer, Antibacterial, Antimalarial.
(b) Balasubramanian, M. Comprehensive Heterocyclic Chemistry II; eds.,, 1996.
[http://dx.doi.org/10.1039/C4RA01814A]
[http://dx.doi.org/10.2174/138955709791012247] [PMID: 20088783]
[http://dx.doi.org/10.1016/j.jsps.2012.03.002] [PMID: 23960814]
[http://dx.doi.org/10.1016/j.ejmech.2023.115549] [PMID: 37321110]
[http://dx.doi.org/10.1016/j.ejmech.2021.113865] [PMID: 34655985]
[PMID: 35240965]
[http://dx.doi.org/10.1021/cm9504753];
(b) Jenekhe, S.A.; Lu, L.; Alam, M.M. New Conjugated Polymers with Donor−Acceptor Architectures: Synthesis and photophysics of carbazole−quinoline and phenothiazine−quinoline copolymers and oligomers exhibiting large intramolecular charge transfer. Macromolecules, 2001, 34(21), 7315-7324.
[http://dx.doi.org/10.1021/ma0100448]
[http://dx.doi.org/10.1021/cr60111a001]
[http://dx.doi.org/10.1002/cber.188201502219]
[http://dx.doi.org/10.1002/anie.198102081];
(b) Gladiali, S.; Chelucci, G.; Mudadu, M.S.; Gastaut, M.A.; Thummel, R.P. Friedländer synthesis of chiral alkyl-substituted 1,10-phenanthrolines. J. Org. Chem., 2001, 66(2), 400-405.
[http://dx.doi.org/10.1021/jo0009806] [PMID: 11429806];
(c) De, S.K.; Gibbs, R.A. A mild and efficient one-step synthesis of quinolines. Tetrahedron Lett., 2005, 46(10), 1647-1649.
[http://dx.doi.org/10.1016/j.tetlet.2005.01.075]
[http://dx.doi.org/10.1021/jo901101v] [PMID: 19572501];
(b) Kulkarni, A.; Török, B. Microwave-assisted multicomponent domino cyclization–aromatization: an efficient approach for the synthesis of substituted quinolines. Green Chem., 2010, 12(5), 875-978.
[http://dx.doi.org/10.1039/c001076f]
[http://dx.doi.org/10.1070/RC1967v036n09ABEH001680]
[http://dx.doi.org/10.1016/j.tet.2008.12.059]
[http://dx.doi.org/10.1002/cber.188702001215]
[http://dx.doi.org/10.1002/prac.18850330110]
[http://dx.doi.org/10.1023/B:COHC.0000028623.41308.e5]
[http://dx.doi.org/10.1080/00397910500184719]
[http://dx.doi.org/10.1021/co500047w] [PMID: 25314670]
[http://dx.doi.org/10.1016/j.tetlet.2014.12.016]
[http://dx.doi.org/10.1039/C7GC01380A]
[http://dx.doi.org/10.3762/bjoc.14.229] [PMID: 30344776]
[http://dx.doi.org/10.1021/acs.joc.7b03198] [PMID: 29345932]
[http://dx.doi.org/10.1021/acs.joc.9b01343] [PMID: 31327228]
[http://dx.doi.org/10.1021/acs.joc.0c01819] [PMID: 33174416]
[http://dx.doi.org/10.1021/acs.orglett.1c03934] [PMID: 34928166]
[http://dx.doi.org/10.1021/acs.joc.1c02708] [PMID: 35076229]
[http://dx.doi.org/10.1021/acs.joc.2c03034] [PMID: 36821870]
[http://dx.doi.org/10.1021/acs.joc.2c02757] [PMID: 36753732]
[http://dx.doi.org/10.1021/acs.joc.3c02152] [PMID: 38044560]
[http://dx.doi.org/10.1128/AAC.42.3.682] [PMID: 9517951]
[http://dx.doi.org/10.1016/S1471-4922(03)00005-9] [PMID: 12643993];
(b) Kevin Baird, J.; Fryauff, D.J.; Hoffman, S.L. Primaquine for prevention of malaria in travelers. Clin. Infect. Dis., 2003, 37(12), 1659-1667.
[http://dx.doi.org/10.1086/379714] [PMID: 14689349]
[http://dx.doi.org/10.1073/pnas.88.11.4786] [PMID: 2052558]
[http://dx.doi.org/10.1016/0006-2952(87)90038-4] [PMID: 3297064]
[http://dx.doi.org/10.1016/0166-6851(86)90095-2] [PMID: 3515180]
[http://dx.doi.org/10.1073/pnas.54.2.521] [PMID: 5324393];
(b) Meshnick, S.R. Chloroquine as intercalator: a hypothesis revived. Parasitol. Today, 1990, 6(3), 77-79.
[http://dx.doi.org/10.1016/0169-4758(90)90215-P] [PMID: 15463303]
[http://dx.doi.org/10.1016/S1286-4579(01)01523-4] [PMID: 11880047]
[http://dx.doi.org/10.1016/j.bmcl.2012.07.028] [PMID: 22850213]
[http://dx.doi.org/10.1016/j.ejmech.2013.08.046] [PMID: 24077524]
[http://dx.doi.org/10.1016/j.bmcl.2012.10.094] [PMID: 23195733]
[http://dx.doi.org/10.1016/j.ejmech.2013.05.023] [PMID: 23792317]
[http://dx.doi.org/10.1021/jm400656s] [PMID: 23837878]
[http://dx.doi.org/10.1021/jm301076q] [PMID: 23102258]
[http://dx.doi.org/10.1021/jm8006905] [PMID: 18774792]
[http://dx.doi.org/10.1073/pnas.0804338105] [PMID: 18987321]
[http://dx.doi.org/10.1021/jm970401y] [PMID: 9371235];
(b) Domarle, O.; Blampain, G.; Agnaniet, H.; Nzadiyabi, T.; Lebibi, J.; Brocard, J.; Maciejewski, L.; Biot, C.; Georges, A.J.; Millet, P. In vitro antimalarial activity of a new organometallic analog, ferrocene-chloroquine. Antimicrob. Agents Chemother., 1998, 42(3), 540-544.
[http://dx.doi.org/10.1128/AAC.42.3.540] [PMID: 9517929];
(c) Dubar, F.; Khalife, J.; Brocard, J.; Dive, D.; Biot, C. Ferroquine, an ingenious antimalarial drug: thoughts on the mechanism of action. Molecules, 2008, 13(11), 2900-2907.
[http://dx.doi.org/10.3390/molecules13112900] [PMID: 19020475]
[http://dx.doi.org/10.1021/jm100117e] [PMID: 20443628]
[http://dx.doi.org/10.1016/j.bmc.2005.02.037] [PMID: 15809160]
[http://dx.doi.org/10.1021/ml4001084] [PMID: 24900724]
[http://dx.doi.org/10.1021/jm0108707] [PMID: 12408708]
[http://dx.doi.org/10.1021/jm030796n] [PMID: 14584944]
[http://dx.doi.org/10.1021/jm061002i] [PMID: 17228883]
[http://dx.doi.org/10.1021/jm00089a025] [PMID: 1597862]
[http://dx.doi.org/10.1016/S0960-894X(02)00475-4] [PMID: 12182868]
[http://dx.doi.org/10.1021/jm060399n] [PMID: 16942036];
(b) Burgess, S.J.; Kelly, J.X.; Shomloo, S.; Wittlin, S.; Brun, R.; Liebmann, K.; Peyton, D.H. Synthesis, structure-activity relationship, and mode-of-action studies of antimalarial reversed chloroquine compounds. J. Med. Chem., 2010, 53(17), 6477-6489.
[http://dx.doi.org/10.1021/jm1006484] [PMID: 20684562]
[http://dx.doi.org/10.3390/molecules21070909] [PMID: 27428939]
[http://dx.doi.org/10.1016/j.bmcl.2015.04.014] [PMID: 25920564]
[http://dx.doi.org/10.1111/cbdd.12321] [PMID: 24803084]
[http://dx.doi.org/10.1016/j.molstruc.2022.134016]
[http://dx.doi.org/10.1016/j.cbi.2023.110379] [PMID: 36738914]
[http://dx.doi.org/10.1080/00397911.2024.2364848]
[http://dx.doi.org/10.1016/j.molstruc.2024.138882]
[http://dx.doi.org/10.1039/D4RA01804D] [PMID: 38867738]
[http://dx.doi.org/10.1517/17425255.1.2.219] [PMID: 16922638]
[http://dx.doi.org/10.2174/1389450033347064] [PMID: 12528988]
[http://dx.doi.org/10.1023/A:1006372102543] [PMID: 10665475]
[http://dx.doi.org/10.1016/j.bmcl.2009.10.065] [PMID: 19879135]
[http://dx.doi.org/10.1002/jhet.749]
[PMID: 21036704]
[http://dx.doi.org/10.1021/ja9106572] [PMID: 20131899]
[http://dx.doi.org/10.1002/anie.200804890] [PMID: 19090514]
[http://dx.doi.org/10.1002/anie.200804107] [PMID: 19097126]
[http://dx.doi.org/10.1021/jm201251c] [PMID: 22206487]
[http://dx.doi.org/10.1021/jm101340q] [PMID: 21405128]
[http://dx.doi.org/10.1016/j.bmcl.2008.04.024] [PMID: 18457950]
[http://dx.doi.org/10.1016/j.bmc.2013.04.013] [PMID: 23628470]
[http://dx.doi.org/10.1016/j.bmc.2013.06.026] [PMID: 23838381]
[http://dx.doi.org/10.1021/jm060712l] [PMID: 17125278]
[http://dx.doi.org/10.1016/j.bmc.2011.12.001] [PMID: 22202437]
[http://dx.doi.org/10.1021/jm8013822] [PMID: 19170519]
[http://dx.doi.org/10.1002/cmdc.201300319] [PMID: 24039190]
[http://dx.doi.org/10.1111/j.1349-7006.1997.tb00320.x] [PMID: 9414662]
[http://dx.doi.org/10.1002/1522-2675(200207)85:7<2214::AID-HLCA2214>3.0.CO;2-W];
(b) Chen, I.L.; Chen, Y.L.; Tzeng, C.C. Chemical constituents from Dehaasia triandra. III. Bisbenzylisoquinoline alkaloids from the leaves and their conformational analysis. Chung Kuo Yao Hsueh Tsa Chih, 2003, 55, 35-47.;
(c) Huang, Y.T.; Huang, D.M.; Guh, J.H.; Chen, I.L.; Tzeng, C.C.; Teng, C.M. CIL-102 interacts with microtubule polymerization and causes mitotic arrest following apoptosis in the human prostate cancer PC-3 cell line. J. Biol. Chem., 2005, 280(4), 2771-2779.
[http://dx.doi.org/10.1074/jbc.M408850200] [PMID: 15536083]
[http://dx.doi.org/10.1016/j.ejmech.2005.04.003] [PMID: 15913847]
[http://dx.doi.org/10.1016/j.bmc.2007.12.028] [PMID: 18180162]
[http://dx.doi.org/10.1021/jm1005447] [PMID: 20662543]
[http://dx.doi.org/10.1021/jm200046z] [PMID: 21599000]
[http://dx.doi.org/10.1016/j.ejmech.2012.11.027] [PMID: 23237975]
[http://dx.doi.org/10.1007/s00044-013-0855-2]
[http://dx.doi.org/10.1016/j.ejmech.2018.11.048] [PMID: 30496987]
[http://dx.doi.org/10.1016/j.ejmech.2018.12.060] [PMID: 30599418]
[http://dx.doi.org/10.1002/ardp.202000086] [PMID: 32537757]
[http://dx.doi.org/10.1111/cbdd.13997] [PMID: 34873844]
[http://dx.doi.org/10.1016/j.ejmech.2022.114434] [PMID: 35551038]
[http://dx.doi.org/10.1016/j.molstruc.2022.133599]
[http://dx.doi.org/10.1021/acs.jmedchem.2c01769] [PMID: 36692906]
[http://dx.doi.org/10.1021/acs.jmedchem.3c00455] [PMID: 37335602]
[PMID: 8387788];
(b) Suzuki, M.; Miura, S.; Mori, M.; Kai, A.; Suzuki, H.; Fukumura, D.; Suematsu, M.; Tsuchiya, M. Rebamipide, a novel antiulcer agent, attenuates Helicobacter pylori induced gastric mucosal cell injury associated with neutrophil derived oxidants. Gut, 1994, 35(10), 1375-1378.
[http://dx.doi.org/10.1136/gut.35.10.1375] [PMID: 7959190];
(c) Hahm, K.B.; Park, I.S.; Kim, Y.S.; Kim, J.H.; Cho, S.W.; Lee, S.I.; Youn, J.K. Role of rebamipide on induction of heat-shock proteins and protection against reactive oxygen metabolite-mediated cell damage in cultured gastric mucosal cells. Free Radic. Biol. Med., 1997, 22(4), 711-716.
[http://dx.doi.org/10.1016/S0891-5849(96)00406-6] [PMID: 9013134];
(d) Hong, W.S.; Jung, H.Y.; Yang, S.K.; Myung, S.J.; Kim, J.H.; Min, Y.I.; Chung, M.H.; Lee, H.S.; Kim, H.W. The antioxidant effect of rebamipide on oxygen free radical production by H. pylori -activated human neutrophils: in comparison with N-acetylcysteine, ascorbic acid and glutathione. Pharmacol. Res., 2001, 44(4), 293-297.
[http://dx.doi.org/10.1006/phrs.2001.0839] [PMID: 11592863]
[http://dx.doi.org/10.1021/jm00164a010] [PMID: 2153816]
[http://dx.doi.org/10.1248/cpb.37.110] [PMID: 2720842]
[http://dx.doi.org/10.1016/S0014-2999(00)00920-1] [PMID: 11137875]
[http://dx.doi.org/10.1159/000028361] [PMID: 10754453]
[http://dx.doi.org/10.1021/jm00096a018] [PMID: 1326634]
[http://dx.doi.org/10.1021/jm00088a021] [PMID: 1316968]
[http://dx.doi.org/10.1248/cpb.43.693] [PMID: 7600619]
[http://dx.doi.org/10.1007/BF02976537] [PMID: 10230503]
[http://dx.doi.org/10.5012/bkcs.2004.25.7.1091]
[http://dx.doi.org/10.1016/S0960-894X(03)00356-1] [PMID: 12798320]
[http://dx.doi.org/10.5152/eurasianjmed.2018.0010] [PMID: 30002579]
[http://dx.doi.org/10.1016/j.bmc.2008.09.052] [PMID: 18835721]
[http://dx.doi.org/10.1002/ardp.200700182] [PMID: 18389515]
[http://dx.doi.org/10.1016/S0968-0896(03)00439-5] [PMID: 12927852]
[http://dx.doi.org/10.1016/j.bmc.2003.10.051] [PMID: 14723957]
[http://dx.doi.org/10.1016/j.bmc.2006.02.039] [PMID: 16524734]
[http://dx.doi.org/10.1002/ardp.201000016] [PMID: 20938950]
[http://dx.doi.org/10.1016/j.bmc.2009.05.084] [PMID: 19560931]
[http://dx.doi.org/10.1016/j.bmcl.2003.10.052] [PMID: 14698178]
[http://dx.doi.org/10.1016/j.ejmech.2012.07.029] [PMID: 22846796]
[http://dx.doi.org/10.1021/acsmedchemlett.7b00545] [PMID: 29541375]
[http://dx.doi.org/10.1016/j.molstruc.2020.128305]
[http://dx.doi.org/10.1002/slct.202002345]
[http://dx.doi.org/10.1016/j.bioorg.2021.105557] [PMID: 34952242]
[http://dx.doi.org/10.1039/D2OB00661H] [PMID: 35579116]
[http://dx.doi.org/10.1016/j.ejmech.2012.12.034] [PMID: 23321259]
[http://dx.doi.org/10.1016/j.ejmech.2009.06.031] [PMID: 19647905]
[http://dx.doi.org/10.1016/j.ejmech.2010.04.022] [PMID: 20537437]
[http://dx.doi.org/10.1016/j.bmcl.2013.05.082] [PMID: 23787100]
[http://dx.doi.org/10.1021/jm200370y] [PMID: 21751791]
[http://dx.doi.org/10.1016/j.bmcl.2013.03.047] [PMID: 23566517]
[http://dx.doi.org/10.1016/j.ejmech.2011.02.060] [PMID: 21444131]
[http://dx.doi.org/10.3390/antibiotics8040239] [PMID: 31795101]
[http://dx.doi.org/10.1016/j.bioorg.2019.103406] [PMID: 31718889]
[http://dx.doi.org/10.1002/ardp.202000277] [PMID: 33078877]
[http://dx.doi.org/10.1038/s41598-022-21435-6] [PMID: 36216981]
[http://dx.doi.org/10.1021/acsomega.2c06871] [PMID: 36643421]
[http://dx.doi.org/10.1016/j.ejmech.2008.04.014] [PMID: 18538452]
[http://dx.doi.org/10.1007/s00044-017-1846-5]
[http://dx.doi.org/10.1016/j.ejmech.2018.05.014] [PMID: 29793211]
[http://dx.doi.org/10.1016/j.bioorg.2018.10.053] [PMID: 30469145]
[http://dx.doi.org/10.1016/j.bioorg.2018.12.025] [PMID: 30605884]
[http://dx.doi.org/10.1016/j.biopha.2021.111857] [PMID: 34323702]
[http://dx.doi.org/10.1021/acs.jmedchem.9b00628] [PMID: 31124675]
[http://dx.doi.org/10.1016/j.ejmech.2023.115863] [PMID: 37837672]
[http://dx.doi.org/10.1021/ml300464h] [PMID: 23930152]
[http://dx.doi.org/10.1016/j.bmc.2011.10.009] [PMID: 22047799]
[http://dx.doi.org/10.1021/jm025553u] [PMID: 12570367]
[http://dx.doi.org/10.2174/1573406410666140526151254] [PMID: 24875825]
[http://dx.doi.org/10.3390/ph16091222] [PMID: 37765030]
[http://dx.doi.org/10.1016/j.bioorg.2018.01.025] [PMID: 29421703]
[http://dx.doi.org/10.1016/j.bmc.2019.07.035] [PMID: 31378594]
[http://dx.doi.org/10.1038/s41598-023-50130-3] [PMID: 38123716]
[http://dx.doi.org/10.1002/open.202400014] [PMID: 38506589]
[http://dx.doi.org/10.1016/j.bioorg.2016.06.001] [PMID: 27289559]
[http://dx.doi.org/10.1021/jm900859q] [PMID: 19663388]
[http://dx.doi.org/10.1021/jm960214k] [PMID: 8765507]
[http://dx.doi.org/10.1016/j.ccr.2023.215453]
[http://dx.doi.org/10.1016/j.inoche.2023.110712]
[http://dx.doi.org/10.1016/j.jinorgbio.2023.112152] [PMID: 36736244]
[http://dx.doi.org/10.1021/acsomega.1c06205] [PMID: 35155932]
[http://dx.doi.org/10.1039/C6MD00251J]
[http://dx.doi.org/10.1021/acs.jmedchem.6b00250] [PMID: 27976900]
[http://dx.doi.org/10.1002/ejic.201601120]