Thia-, Oxa-, and Aza Heterocyclic Derivatives Based on Thiochroman- and Benzothiepine 1,1-dioxide Moieties: Syntheses, Characterization, Antimicrobial-, Antituberculosis-, and Anticancer Activity

Abstract

A series of thia-, oxa-, and aza heterocyclic derivatives based on 3,4-dihydro-1-benzothiepin-5(2H)-one 1,1-dioxide, and 2,3-dihydro-4H-thiochroman-4-one 1,1-dioxide moieties were prepared from the  diketoesters 2 and 11.  All derivatives were evaluated on a few Gram-positive and Gram-negative bacterial strains, as well as the fungal strains. It would also be noticed that the benzodiazepine derivatives 9 and 18 exhibited better antibacterial potentials than the rest. 1,2-Diphenylethane-1,2-diamine substituted thiochromeno- and benzothiepino derivatives 9 and 18 showed good inhibitory activity against MTB (H₃₇Rv) at MIC 7.0 and 6.5 µM. Compounds 9 and 18 were found to exhibit higher cytotoxic potency (15, 13 µM and 14, 12 µM) than that of doxorubicin (21 µM and 19 µM) against HeLa cell and HCT116 cell.