Abstract
The therapeutic potential of the majority of the marketed drugs is due to the presence of a heterocyclic nucleus, which constitutes a huge role in the field of medicinal chemistry. These heterocyclic scaffolds could act as a template in order to design potential therapeutic agents against several diseases. Benzothiazole scaffold is one of the influential heteroaromatic rings in the field of medicinal chemistry owing to its extensive pharmacological features. Herein, we have focused on the synthesis of benzothiazole-based medicinal molecules, which possess antimicrobial and anti-inflammatory activities. This review covers a systematic description of synthetic routes for biologically relevant benzothiazole derivatives in the last five years. The main aim of this study is to show the diversification of benzothiazole-based molecules into their pharmacologically more active derivatives. This review's synthetic protocols include metal-free, metal-catalyzed, and metal precursor azo dyes strategies for the development of benzothiazole derived bioactive compounds. The discussion under the various headings covers synthetic schemes and biological activities of the most potent molecules in the form of minimum inhibitory concentration.
Keywords: Benzothiazole, heterocyclic scaffolds, antimicrobial, anti-inflammatory activity, synthetic method, COX.
Graphical Abstract
[http://dx.doi.org/10.1016/j.ejmech.2016.08.062] [PMID: 27639370]
[http://dx.doi.org/10.1021/cr020033s] [PMID: 12630855]
[http://dx.doi.org/10.3390/molecules25071675] [PMID: 32260500]
[http://dx.doi.org/10.1007/BF01715638] [PMID: 9249758]
[http://dx.doi.org/10.1021/jo00031a035]
[http://dx.doi.org/10.1038/s41598-017-02489-3] [PMID: 28566733]
[http://dx.doi.org/10.4103/0250-474X.32107]
[http://dx.doi.org/10.1016/j.ejmech.2015.08.033] [PMID: 26318068]
[http://dx.doi.org/10.1038/sj.bjc.6600719] [PMID: 12569393]
[http://dx.doi.org/10.1054/bjoc.2000.1231] [PMID: 10901382]
[http://dx.doi.org/10.1016/j.ejmech.2014.07.097] [PMID: 25127150]
[http://dx.doi.org/10.1007/s00044-011-9791-1]
[http://dx.doi.org/10.1016/j.bmc.2017.07.057] [PMID: 28789907]
[http://dx.doi.org/10.1016/j.bioorg.2018.12.021] [PMID: 30599411]
[http://dx.doi.org/10.1016/j.etap.2020.103415] [PMID: 32470609]
[http://dx.doi.org/10.1007/s00044-015-1410-0]
[http://dx.doi.org/10.2174/1568026618666180206101814] [PMID: 29412109]
[http://dx.doi.org/10.1007/s11164-013-1367-x]
[http://dx.doi.org/10.1016/j.bioorg.2020.104608] [PMID: 33465668]
[http://dx.doi.org/10.1038/srep37730] [PMID: 27883048]
[http://dx.doi.org/10.1002/pola.26144]
[http://dx.doi.org/10.1016/j.ejmech.2014.10.059] [PMID: 25462241]
[http://dx.doi.org/10.3797/scipharm.1204-27] [PMID: 23264933]
[http://dx.doi.org/10.24820/ark.5550190.p010.664]
[PMID: 8624439]
[http://dx.doi.org/10.1007/s00044-012-0416-0]
[http://dx.doi.org/10.1155/2013/345198]
[http://dx.doi.org/10.1016/j.dyepig.2005.10.003]
[http://dx.doi.org/10.1136/ard.62.6.501] [PMID: 12759283]
[http://dx.doi.org/10.1016/j.bmc.2014.09.028] [PMID: 25311566]
[http://dx.doi.org/10.1016/j.molstruc.2006.11.023]
[http://dx.doi.org/10.1016/j.tetlet.2010.12.057]
[http://dx.doi.org/10.1002/ejoc.201901502]
[http://dx.doi.org/10.1021/ol400379z] [PMID: 23496117]
[http://dx.doi.org/10.1039/C6DT01063F] [PMID: 27143346]
[http://dx.doi.org/10.2174/1570179417666200117110758] [PMID: 32003698]
[http://dx.doi.org/10.1021/om401128z]
[http://dx.doi.org/10.3906/kim-1512-44]
[http://dx.doi.org/10.1039/C3RA46955G]
[http://dx.doi.org/10.1007/s11426-020-9811-6]
[http://dx.doi.org/10.1016/j.ejmech.2016.07.067] [PMID: 27494168]
[http://dx.doi.org/10.1007/s11164-016-2599-3]
[http://dx.doi.org/10.1016/j.arabjc.2011.12.006]
[http://dx.doi.org/10.1007/s11164-016-2454-6]
[http://dx.doi.org/10.1007/s00044-017-1894-x]
[http://dx.doi.org/10.1007/s00044-017-1898-6]
[http://dx.doi.org/10.1021/acs.jafc.7b04130] [PMID: 29099589]
[http://dx.doi.org/10.1002/jhet.2929]
[http://dx.doi.org/10.1002/slct.201801936]
[http://dx.doi.org/10.1016/j.bmc.2018.05.015] [PMID: 29778528]
[http://dx.doi.org/10.1016/j.molstruc.2018.07.007]
[http://dx.doi.org/10.1007/s00044-019-02420-7]
[http://dx.doi.org/10.1002/ardp.201800341] [PMID: 31245880]
[http://dx.doi.org/10.1016/j.compbiolchem.2019.01.003] [PMID: 30639681]
[http://dx.doi.org/10.1002/slct.201901312]
[http://dx.doi.org/10.1002/jhet.3624]
[http://dx.doi.org/10.1134/S1070363219090226]
[http://dx.doi.org/10.1016/j.rechem.2019.100006]
[http://dx.doi.org/10.1007/s00706-019-02399-2]
[http://dx.doi.org/10.1016/j.cdc.2020.100362]
[http://dx.doi.org/10.1016/j.jorganchem.2020.121225]
[http://dx.doi.org/10.1007/s11243-020-00435-3]
[http://dx.doi.org/10.1007/s12039-020-01844-8]
[http://dx.doi.org/10.1007/s10904-020-01632-4]
[http://dx.doi.org/10.1080/00397911.2020.1791342]
[http://dx.doi.org/10.1007/s11243-020-00439-z]
[http://dx.doi.org/10.1016/j.bioorg.2016.06.004] [PMID: 27376460]
[http://dx.doi.org/10.1016/j.bioorg.2018.09.015] [PMID: 30253336]
[http://dx.doi.org/10.1080/14756366.2018.1426573] [PMID: 29372659]
[http://dx.doi.org/10.1016/j.ejmech.2019.07.002] [PMID: 31302448]
[http://dx.doi.org/10.1002/slct.201902972]
[http://dx.doi.org/10.1016/j.molstruc.2020.128477]
[http://dx.doi.org/10.1016/j.bmcl.2020.127237] [PMID: 32386981]
[http://dx.doi.org/10.2174/2212796813666191118100520]