Abstract
Due to their diverse applications in industrial and synthetic organic chemistry, quinoline and 1,3,4-oxadiazole have become important heterocyclic compounds. Quinoline and 1,3,4- oxadiazole compounds have been developed for various medical conditions such as anti-cancer, anti-bacterial, anti-fungal, antimalarial, antioxidants, anti-HIV, anticonvulsant, antiviral, etc. The current review includes synthetic protocols for biologically active 1,3,4-oxadiazole incorporating quinoline hybrids with their structure-activity relationship to explore work (Mainly from 2010 to 2021) based on 1,3,4-oxadiazole-quinoline hybrids to the medicinal chemist for further research in the development of the molecule.
Keywords: Oxadiazole, Quinoline, Oxadiazole-quinoline hybrids, Synthetic Approaches, Biological Activity, Structure-Activity Relationship
Graphical Abstract
[http://dx.doi.org/10.1016/j.bioorg.2021.104639] [PMID: 33618829]
[http://dx.doi.org/10.1002/jhet.3907]
[http://dx.doi.org/10.1016/j.radphyschem.2021.109471]
[PMID: 23190035]
[http://dx.doi.org/10.1016/j.bmc.2020.115973] [PMID: 33444846]
[http://dx.doi.org/10.2174/092986711795328382] [PMID: 21428893]
[http://dx.doi.org/10.1002/slct.202002790]
[http://dx.doi.org/10.1021/co500002s] [PMID: 24749663]
[http://dx.doi.org/10.1016/j.arabjc.2016.10.009]
[http://dx.doi.org/10.1002/jbt.22260] [PMID: 30431695]
[http://dx.doi.org/10.1002/ardp.201800355] [PMID: 31081954]
[http://dx.doi.org/10.1016/j.cdc.2020.100423]
[http://dx.doi.org/10.1016/j.bmcl.2010.09.018] [PMID: 20947350]
[http://dx.doi.org/10.1016/j.molstruc.2017.11.118]
[http://dx.doi.org/10.1111/j.1747-0285.2011.01255.x] [PMID: 21985632]
[http://dx.doi.org/10.1016/j.ejmech.2008.07.010] [PMID: 18752871]
[http://dx.doi.org/10.3390/molecules24030548] [PMID: 30717338]
[http://dx.doi.org/10.1002/ardp.202000232] [PMID: 33210348]
[http://dx.doi.org/10.1016/j.molstruc.2021.131217]
[http://dx.doi.org/10.1016/j.bmcl.2015.04.014] [PMID: 25920564]
[http://dx.doi.org/10.1016/j.bmc.2014.12.018] [PMID: 25593097]
[http://dx.doi.org/10.1016/j.biopha.2014.10.007] [PMID: 25458785]
[http://dx.doi.org/10.1002/jhet.3241]
[http://dx.doi.org/10.1002/jhet.3031]
[http://dx.doi.org/10.1002/ardp.201800382] [PMID: 31021468]
[http://dx.doi.org/10.1002/ardp.201900045] [PMID: 31274223]
[http://dx.doi.org/10.1039/C4OB02247E] [PMID: 25503645]
[http://dx.doi.org/10.1186/s42358-020-00134-8] [PMID: 32517786]
[http://dx.doi.org/10.3390/molecules22061001] [PMID: 28621733]
[http://dx.doi.org/10.1039/C5MD00280J]
[http://dx.doi.org/10.1016/j.bioorg.2018.01.025] [PMID: 29421703]
[http://dx.doi.org/10.1039/C5RA08778C]
[http://dx.doi.org/10.1016/j.bmc.2020.115511] [PMID: 32336669]
[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/10.3390/molecules23030672] [PMID: 29547522]
[http://dx.doi.org/10.1016/j.ejmech.2021.113220] [PMID: 33609889]
[http://dx.doi.org/10.2174/138955712801264800] [PMID: 22512560]
[http://dx.doi.org/10.3390/molecules170910192] [PMID: 22926303]
[http://dx.doi.org/10.1080/00397911.2013.879901]
[http://dx.doi.org/10.3390/ijms21228692] [PMID: 33217987]
[http://dx.doi.org/10.1021/acsomega.0c05718] [PMID: 33490827]
[http://dx.doi.org/10.1016/j.bmcl.2012.08.061] [PMID: 22967765]
[http://dx.doi.org/10.1016/j.bmc.2019.115097] [PMID: 31540826]
[http://dx.doi.org/10.1016/j.ejmech.2011.12.013] [PMID: 22204901]
[http://dx.doi.org/10.1016/j.bioorg.2021.104873] [PMID: 33845381]
[http://dx.doi.org/10.32628/IJSRST207234]
[http://dx.doi.org/10.3390/ph14050438] [PMID: 34066442]
[http://dx.doi.org/10.1016/j.molstruc.2020.128357]
[http://dx.doi.org/10.3390/ijms22136979] [PMID: 34209520]
[http://dx.doi.org/10.1111/j.1747-0285.2011.01316.x] [PMID: 22212247]
[http://dx.doi.org/10.1016/j.cdc.2020.100431]
[http://dx.doi.org/10.1016/j.ejmech.2020.112886] [PMID: 33032083]
[http://dx.doi.org/10.1016/j.bmcl.2016.02.043] [PMID: 26920799]
[PMID: 28137242]
[http://dx.doi.org/10.1007/s12154-016-0153-9] [PMID: 27493696]
[http://dx.doi.org/10.1016/j.ejmech.2012.10.007] [PMID: 23149297]
[http://dx.doi.org/10.1016/j.bmc.2021.116330] [PMID: 34333395]
[http://dx.doi.org/10.1016/j.molstruc.2020.128705]
[http://dx.doi.org/10.1016/j.bmc.2015.06.053] [PMID: 26164624]
[http://dx.doi.org/10.1016/j.bioorg.2018.10.025] [PMID: 30339863]
[http://dx.doi.org/10.1016/j.bioorg.2021.105046] [PMID: 34126575]
[http://dx.doi.org/10.1016/j.arabjc.2020.03.009]
[http://dx.doi.org/10.1002/ardp.201900342] [PMID: 32319117]
[http://dx.doi.org/10.1007/s11164-016-2794-2]
[http://dx.doi.org/10.1039/C5NJ02566D]
[http://dx.doi.org/10.1016/j.jscs.2011.09.005]
[http://dx.doi.org/10.1016/j.arabjc.2012.04.018]
[http://dx.doi.org/10.1016/j.bioorg.2021.104920] [PMID: 33910078]
[http://dx.doi.org/10.1002/jhet.653]
[http://dx.doi.org/10.1016/j.bmcl.2010.10.111] [PMID: 21074427]
[http://dx.doi.org/10.1002/jhet.1005]
[http://dx.doi.org/10.1016/j.ejmech.2007.03.013] [PMID: 17521777]
[http://dx.doi.org/10.1039/C4RA04456H]
[http://dx.doi.org/10.1016/j.ejmech.2011.04.035] [PMID: 21689870]
[http://dx.doi.org/10.2174/1570180814666170823163540]
[http://dx.doi.org/10.1002/jccs.201600199]
[http://dx.doi.org/10.1016/j.ejps.2019.104966] [PMID: 31233865]
[http://dx.doi.org/10.1016/j.arabjc.2011.05.004]
[http://dx.doi.org/10.1016/j.cdc.2021.100716]
[http://dx.doi.org/10.1002/jhet.2529]
[http://dx.doi.org/10.3390/ph14050399] [PMID: 33922361]
[http://dx.doi.org/10.31788/RJC.2020.1315593]
[http://dx.doi.org/10.2174/157340611797928334] [PMID: 22313306]
[http://dx.doi.org/10.14233/ajchem.2019.22061]
[http://dx.doi.org/10.1016/j.ejmech.2020.112672] [PMID: 32798790]
[http://dx.doi.org/10.1016/j.ejmech.2012.11.039] [PMID: 23279864]
[http://dx.doi.org/10.3390/molecules24071274] [PMID: 30986908]
[http://dx.doi.org/10.1080/14756366.2019.1605364] [PMID: 31072147]
[http://dx.doi.org/10.1002/slct.201902797]
[http://dx.doi.org/10.3390/ph13110393] [PMID: 33203182]
[http://dx.doi.org/10.1155/2014/491492] [PMID: 25177693]
[http://dx.doi.org/10.1016/j.ejmech.2019.111867] [PMID: 31757525]
[http://dx.doi.org/10.1021/acs.jmedchem.8b01938] [PMID: 30897325]
[http://dx.doi.org/10.3390/molecules21070909] [PMID: 27428939]
[http://dx.doi.org/10.1016/j.bioorg.2017.02.005] [PMID: 28228228]
[http://dx.doi.org/10.1080/10426507.2017.1394302]
[http://dx.doi.org/10.1002/ardp.201500238] [PMID: 26435294]
[http://dx.doi.org/10.1021/acsomega.8b01476] [PMID: 30411010]