Abstract
Heterocyclic compounds are fundamental building blocks for developing novel bioactive compounds. Due to their extensive uses in both industrial and synthetic organic chemistry, quinoline and benzimidazole have recently become important heterocycles. Clinical trials have investigated quinoline and benzimidazole analogues to treat a variety of illnesses, including cancer, bacterial and fungal infection, DNA damage, etc. Medicinal chemists are paying attention to nitrogen-containing hybrid heterocyclic compounds that have a wide range of therapeutical potential with lesser adverse effects. Many efforts have been made to find new and more efficient ways to synthesize these molecules. However, microbial resistance is becoming a major threat to the scientific community; hence, the necessity for the discovery and development of novel antimicrobial drugs with novel modes of action is becoming highly significant. One strategy to overcome this problem is to produce hybrid molecules by combining two or more bioactive heterocyclic moieties in a single molecular platform. Based on established research data on quinoline- bearing benzimidazole derivatives, it can be concluded that both moieties are used for the synthesis of promising therapeutically active agents. This present review comprises the synthetic approaches of biologically active quinolines containing benzimidazole derivatives with their structure-activity relationship studies to provide an overview of the work done on quinoline derivatives to the medicinal chemist for future research.
Graphical Abstract
[http://dx.doi.org/10.1039/D0RA03763J] [PMID: 35517753]
[http://dx.doi.org/10.1016/j.arabjc.2016.10.009]
[http://dx.doi.org/10.1016/j.bmc.2020.115973] [PMID: 33444846]
[http://dx.doi.org/10.1002/slct.202002790]
[http://dx.doi.org/10.5539/ijc.v12n1p99]
[http://dx.doi.org/10.1016/j.bioorg.2020.104612] [PMID: 33476869]
[http://dx.doi.org/10.1039/C6NJ03913H]
[http://dx.doi.org/10.1016/j.bioorg.2020.104419] [PMID: 33142228]
[http://dx.doi.org/10.1002/ardp.202000086] [PMID: 32537757]
[http://dx.doi.org/10.2174/092986711795328382] [PMID: 21428893]
[http://dx.doi.org/10.1007/s11164-016-2794-2]
[http://dx.doi.org/10.1002/slct.201803078]
[http://dx.doi.org/10.1016/j.ejmech.2010.01.060] [PMID: 20153559]
[http://dx.doi.org/10.2174/1871523018666190115092215] [PMID: 30648525]
[http://dx.doi.org/10.1016/S0968-0896(01)00116-X] [PMID: 11504637]
[http://dx.doi.org/10.2174/092986710791163966] [PMID: 20377510]
[http://dx.doi.org/10.1021/acs.jmedchem.7b00738] [PMID: 29215279]
[http://dx.doi.org/10.1016/j.trstmh.2004.01.013] [PMID: 15550254]
[http://dx.doi.org/10.1016/j.bmcl.2015.02.025] [PMID: 25754489]
[http://dx.doi.org/10.1248/bpb.27.1683] [PMID: 15467220]
[http://dx.doi.org/10.1039/C5RA08778C]
[http://dx.doi.org/10.3109/14756366.2013.845820] [PMID: 24156743]
[http://dx.doi.org/10.3109/14756366.2012.755622] [PMID: 23327639]
[http://dx.doi.org/10.1016/j.bmc.2011.01.047] [PMID: 21371895]
[http://dx.doi.org/10.1016/j.ejmech.2021.113220] [PMID: 33609889]
[http://dx.doi.org/10.3390/molecules23030672] [PMID: 29547522]
[http://dx.doi.org/10.1016/j.ejmech.2019.03.030] [PMID: 30939352]
[http://dx.doi.org/10.32471/exp-oncology.2312-8852.vol-41-no-1.12414] [PMID: 30932417]
[http://dx.doi.org/10.1016/j.bmcl.2010.10.116] [PMID: 21071221]
[http://dx.doi.org/10.1021/jm900003c] [PMID: 19271749]
[http://dx.doi.org/10.1016/S0968-0896(02)00094-9] [PMID: 12057669]
[http://dx.doi.org/10.2174/138945006777709557] [PMID: 16842215]
[http://dx.doi.org/10.1078/094471103321659924] [PMID: 12725575]
[http://dx.doi.org/10.22270/jddt.v6i3.1234]
[http://dx.doi.org/10.1080/10406638.2021.1942933]
[http://dx.doi.org/10.46624/ajptr.2019.v9.i3.021]
[http://dx.doi.org/10.1002/slct.201904832]
[http://dx.doi.org/10.1016/j.bioorg.2017.08.015] [PMID: 28881255]
[http://dx.doi.org/10.5772/intechopen.90758]
[http://dx.doi.org/10.4172/2161-0444.1000498]
[http://dx.doi.org/10.1111/cbdd.12442] [PMID: 25283264]
[http://dx.doi.org/10.1016/j.jscs.2011.03.005]
[http://dx.doi.org/10.3390/cancers11122042] [PMID: 31861153]
[http://dx.doi.org/10.1016/j.apsb.2015.05.003] [PMID: 26579464]
[http://dx.doi.org/10.1016/j.ejmech.2014.01.030] [PMID: 24602792]
[http://dx.doi.org/10.1016/j.ejmech.2010.01.029] [PMID: 20133024]
[http://dx.doi.org/10.1016/j.bmc.2010.09.019] [PMID: 20888242]
[http://dx.doi.org/10.1016/j.bmcl.2008.05.009] [PMID: 18486471]
[http://dx.doi.org/10.1080/00397911.2020.1725057]
[http://dx.doi.org/10.1002/ardp.201700205] [PMID: 29356105]
[http://dx.doi.org/10.1007/s11094-019-01976-3]
[http://dx.doi.org/10.1016/j.bmc.2014.06.043] [PMID: 25082514]
[http://dx.doi.org/10.1016/j.ejbas.2017.09.002]
[http://dx.doi.org/10.2174/2213335606666190429124745]
[http://dx.doi.org/10.1007/s00044-016-1570-6]
[http://dx.doi.org/10.1186/s13065-019-0579-6] [PMID: 31384813]
[http://dx.doi.org/10.1039/C9NJ01948K]
[http://dx.doi.org/10.1080/10406638.2018.1441877]
[http://dx.doi.org/10.1080/14756366.2016.1190711] [PMID: 27250919]
[http://dx.doi.org/10.2174/1871520616666151103113412] [PMID: 26526461]
[http://dx.doi.org/10.1039/c3md00193h]
[http://dx.doi.org/10.1016/j.ejmech.2018.07.066] [PMID: 30092368]
[http://dx.doi.org/10.1016/j.bmc.2011.09.002] [PMID: 21964184]
[http://dx.doi.org/10.1016/j.jinorgbio.2019.110816] [PMID: 31518868]
[http://dx.doi.org/10.1016/j.poly.2020.114369]
[http://dx.doi.org/10.1016/j.bmc.2013.10.035] [PMID: 24238902]
[http://dx.doi.org/10.1039/C8NJ00416A]
[http://dx.doi.org/10.1080/14756366.2018.1533822] [PMID: 30422010]
[http://dx.doi.org/10.1016/j.cdc.2020.100556]
[http://dx.doi.org/10.1002/ardp.202100074] [PMID: 34346099]
[http://dx.doi.org/10.1016/j.bmcl.2017.07.051] [PMID: 28789894]
[http://dx.doi.org/10.1016/j.ejmech.2019.111845] [PMID: 31718941]
[http://dx.doi.org/10.1016/j.ejmech.2014.07.071] [PMID: 25064347]
[http://dx.doi.org/10.1016/j.ejmech.2017.07.027] [PMID: 28753517]
[http://dx.doi.org/10.1016/j.ejmech.2010.02.022] [PMID: 20207049]
[http://dx.doi.org/10.1021/jm070876h] [PMID: 17935309]
[http://dx.doi.org/10.1016/j.bmcl.2006.03.059] [PMID: 16603354]
[http://dx.doi.org/10.1016/j.bmc.2018.12.016] [PMID: 30563725]
[http://dx.doi.org/10.1016/j.molstruc.2017.07.020]
[http://dx.doi.org/10.1016/j.ejmech.2012.05.027] [PMID: 22732060]
[http://dx.doi.org/10.1016/j.ejmech.2016.01.052] [PMID: 26871658]
[http://dx.doi.org/10.46624/ajphr.2018.v6.i12.004]
[http://dx.doi.org/10.1007/s00044-012-0322-5]
[http://dx.doi.org/10.1016/j.ejmech.2017.05.064] [PMID: 28623814]
[http://dx.doi.org/10.1007/s13369-021-05749-7]
[http://dx.doi.org/10.1002/cmdc.201700739] [PMID: 29512892]
[http://dx.doi.org/10.1016/j.bmcl.2009.05.019] [PMID: 19477639]
[http://dx.doi.org/10.1007/s00044-010-9388-0]
[http://dx.doi.org/10.1016/j.bmcl.2019.01.006] [PMID: 30655213]
[http://dx.doi.org/10.1007/BF02291946]
[http://dx.doi.org/10.1007/s10593-011-0673-8]
[http://dx.doi.org/10.1021/acs.jmedchem.0c01129] [PMID: 32787113]
[http://dx.doi.org/10.1016/j.ejmech.2020.112694] [PMID: 32861176]
[http://dx.doi.org/10.1016/j.ejmech.2019.06.069] [PMID: 31301563]
[http://dx.doi.org/10.14233/ajchem.2019.22061]
[http://dx.doi.org/10.1021/acsomega.8b01476] [PMID: 30411010]
[http://dx.doi.org/10.1016/j.jfluchem.2014.02.012]