Abstract
Quinoline derivatives are an important class of heterocyclic compounds and possess various applications in synthetic organic chemistry, medicinal chemistry, material chemistry and natural product chemistry. This review article describes the different quinoline derivatives having antimalarial, analgesic, anti-inflammatory, antineoplastic, antibacterial, antifungal, antiviral, anthelmintic, antiprotozoal, cardiovascular, CNS and other useful bioactivities. We have delineated the general synthetic routes for the synthesis of many bioactive quinoline based heterocycles. In addition to this, we have also discussed the crucial synthetic routes as well as their mechanistic paths for the formation of bioactive quinoline derivatives. The study shows that substitution at the 4 and 8- position of quinoline is more crucial for bioactivity as compared to other positions.
Keywords: Quinoline, Heterocycles, Bioactive, Synthesis, antimalarial Quinoline, antimalarial
Graphical Abstract
[http://dx.doi.org/10.1016/bs.aihch.2020.01.001]
[PMID: 23190035]
[PMID: 22365088]
[http://dx.doi.org/10.1021/cr60095a007]
[http://dx.doi.org/10.1021/jo952103j]
[http://dx.doi.org/10.1016/S0223-5234(00)01175-2] [PMID: 11137230]
[http://dx.doi.org/10.1021/jm0100335] [PMID: 11428933]
[http://dx.doi.org/10.1021/ol006321x] [PMID: 11009360]
[http://dx.doi.org/10.2174/138955709791012247] [PMID: 20088783]
[http://dx.doi.org/10.1016/S0968-0896(03)00439-5] [PMID: 12927852]
[http://dx.doi.org/10.1016/S0960-894X(02)00173-7] [PMID: 11992775]
[http://dx.doi.org/10.1351/pac199062071303]
[http://dx.doi.org/10.1021/jm00367a019] [PMID: 6361258]
[http://dx.doi.org/10.1021/jm0400193] [PMID: 15214793]
[http://dx.doi.org/10.1021/jm00213a024] [PMID: 845876]
[http://dx.doi.org/10.1039/b009171p] [PMID: 11827390]
[http://dx.doi.org/10.3329/bmrcb.v35i2.2564] [PMID: 20120779]
[http://dx.doi.org/10.1016/S0968-0896(02)00046-9] [PMID: 11937327]
[http://dx.doi.org/10.1016/j.bmcl.2005.07.051] [PMID: 16139502]
[http://dx.doi.org/10.1016/j.ejmech.2007.01.004] [PMID: 17331623]
[http://dx.doi.org/10.3390/molecules13112880] [PMID: 19020473]
[http://dx.doi.org/10.1016/S0223-5234(02)01355-7] [PMID: 12008057]
[http://dx.doi.org/10.1016/S0960-894X(98)00201-7] [PMID: 9871745]
[http://dx.doi.org/10.1021/jm00040a003] [PMID: 8035419]
[http://dx.doi.org/10.1016/j.bmcl.2004.03.005] [PMID: 15109635]
[http://dx.doi.org/10.1021/jm980043e] [PMID: 9667973]
[http://dx.doi.org/10.1038/nrd1660] [PMID: 15729361]
[http://dx.doi.org/10.1248/cpb.55.894] [PMID: 17541188]
[http://dx.doi.org/10.1016/j.bmcl.2007.01.038] [PMID: 17276057]
[http://dx.doi.org/10.1146/annurev.bi.54.070185.003313] [PMID: 2992360]
[http://dx.doi.org/10.1093/jac/dkn136] [PMID: 18390884]
[http://dx.doi.org/10.1007/s00044-008-9092-5]
[http://dx.doi.org/10.1023/B:JCAM.0000004622.13865.4f] [PMID: 14703120]
[http://dx.doi.org/10.1021/jm9509408] [PMID: 8978845]
[http://dx.doi.org/10.1021/jm100329q] [PMID: 20545360]
[http://dx.doi.org/10.1002/med.21703] [PMID: 32729169]
[http://dx.doi.org/10.3390/molecules26113374] [PMID: 34204857]
[http://dx.doi.org/10.1039/C4RA01814A]
[http://dx.doi.org/10.1002/anie.200200569] [PMID: 14613157]
[http://dx.doi.org/10.1039/C5OB01379H] [PMID: 26278395]
[http://dx.doi.org/10.1016/j.ejmech.2014.02.005] [PMID: 24583357]
[http://dx.doi.org/10.1002/14356007.a22_465]
[http://dx.doi.org/10.1021/jm0010670] [PMID: 11448225]
[http://dx.doi.org/10.4103/0976-500X.77119] [PMID: 21701651]
[http://dx.doi.org/10.1016/j.jfluchem.2009.01.002]
[http://dx.doi.org/10.1007/s10562-007-9127-4]
[http://dx.doi.org/10.2174/157017808783330261]
[http://dx.doi.org/10.1016/j.tetlet.2008.09.097]
[http://dx.doi.org/10.1016/j.bioorg.2019.103406] [PMID: 31718889]
[http://dx.doi.org/10.1016/j.tet.2008.12.039]
[http://dx.doi.org/10.1055/s-0030-1259065]
[http://dx.doi.org/10.1016/j.ultsonch.2010.07.020] [PMID: 20719553]
[http://dx.doi.org/10.1021/jo1017525] [PMID: 20936825]
[http://dx.doi.org/10.1055/s-0028-1087340]
[http://dx.doi.org/10.1021/jm101340q] [PMID: 21405128]
[http://dx.doi.org/10.1021/jo801678n] [PMID: 18937410]
[http://dx.doi.org/10.1016/j.bmc.2006.02.039] [PMID: 16524734]
[http://dx.doi.org/10.1021/ol8016726] [PMID: 18722456]
[http://dx.doi.org/10.1021/jo9026116] [PMID: 20088585]
[http://dx.doi.org/10.1021/jo902603v] [PMID: 20099928]
[http://dx.doi.org/10.1016/j.bioorg.2021.104639] [PMID: 33618829]
[http://dx.doi.org/10.1016/j.bmc.2009.08.003] [PMID: 19703776]
[http://dx.doi.org/10.1016/0006-2952(96)00306-1] [PMID: 8759027]
[http://dx.doi.org/10.1016/j.bmcl.2007.07.049] [PMID: 17768052]
[http://dx.doi.org/10.1021/jm100911f] [PMID: 21141892]
[http://dx.doi.org/10.1007/s00044-010-9397-z]
[http://dx.doi.org/10.1016/j.bmc.2005.05.053] [PMID: 16002298]
[http://dx.doi.org/10.1016/j.bmcl.2008.10.065] [PMID: 18974001]
[http://dx.doi.org/10.1007/s00044-010-9522-z]
[http://dx.doi.org/10.1016/j.bmcl.2008.12.046] [PMID: 19112018]
[http://dx.doi.org/10.1016/j.bmcl.2008.12.097] [PMID: 19144517]
[http://dx.doi.org/10.1016/j.bmcl.2008.11.037] [PMID: 19041240]
[http://dx.doi.org/10.1016/j.bmcl.2008.11.078] [PMID: 19095449]
[http://dx.doi.org/10.1016/j.bmc.2009.02.026] [PMID: 19285414]
[http://dx.doi.org/10.1016/j.bmc.2009.01.013] [PMID: 19188070]
[http://dx.doi.org/10.1021/jm900003c] [PMID: 19271749]
[http://dx.doi.org/10.1016/j.ejmech.2010.04.022] [PMID: 20537437]
[http://dx.doi.org/10.1016/j.bmc.2007.08.009] [PMID: 17765545]
[http://dx.doi.org/10.1007/s00044-010-9463-6]
[http://dx.doi.org/10.1007/s00044-008-9138-8]
[http://dx.doi.org/10.1016/j.bioorg.2021.105117] [PMID: 34214752]
[http://dx.doi.org/10.1016/j.ijantimicag.2008.05.001] [PMID: 18674886]
[http://dx.doi.org/10.1016/j.bmc.2009.01.038] [PMID: 19217787]
[http://dx.doi.org/10.1016/j.bmc.2003.09.007] [PMID: 14604664]
[http://dx.doi.org/10.22270/jddt.v12i4.5561]
[http://dx.doi.org/10.1016/j.bmcl.2005.07.044] [PMID: 16165359]
[http://dx.doi.org/10.1016/j.bmc.2007.08.044] [PMID: 17851082]
[http://dx.doi.org/10.1016/1043-6618(90)90729-W] [PMID: 2367281]
[http://dx.doi.org/10.1016/j.bmc.2008.12.048] [PMID: 19162487]
[http://dx.doi.org/10.1016/j.bmc.2007.03.013] [PMID: 17391964]
[http://dx.doi.org/10.1016/j.bmcl.2008.12.005] [PMID: 19117759]
[http://dx.doi.org/10.1016/S0960-894X(00)00354-1] [PMID: 10969979]
[http://dx.doi.org/10.1016/j.bmcl.2009.01.045] [PMID: 19195882]
[http://dx.doi.org/10.1021/jm101501b] [PMID: 21395312]
[http://dx.doi.org/10.1016/j.bmcl.2003.12.090] [PMID: 15006407]
[http://dx.doi.org/10.1002/ardp.202000291] [PMID: 33283901]