Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles

Abstract

Using molecular simplification and molecular hybridization approaches, a series of 2-(benzylthio)-1H-benzo[d]imidazoles was synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (M. tuberculosis) growth. Compounds 6p and 6z were considered the lead compounds from this series of molecules, with minimal inhibitory concentration (MIC) values of 6.9 and 3.8 μM against M. tuberculosis H37Rv, respectively. Additionally, the leading compounds were active against multidrug-resistant strains and were devoid of apparent toxicity to Vero and HepG2 cells, from 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and neutral red assays. Finally, the compounds presented good aqueous solubility and high plasma stability. These data together indicate that this class of molecules may furnish new anti-tuberculosis drug candidates for future development.

DBU-Promoted Deaminative Thiolation of 1H-Benzo[d]imidazol-2-amines and Benzo[d]oxazol-2-amines

“…1 H -Benzo­[ d ]­imidazoles and benzo­[ d ]­oxazoles are important N-heterocyclic compounds as key structural units of synthetic intermediates, pharmaceuticals, agrochemicals, and natural products. , Among the two abovementioned N-heterocycles known, 2-thio-1 H -benzo­[ d ]­imidazoles and 2-thiobenzo­[ d ]­oxazoles play a central role as privileged pharmacophores in various bioactive molecules . For example, compound ( I ) and compound ( II ) are used as antiprotozoal and antihelminthic agents in the field of antiparasitic infections, respectively (Figure ).…”