Synthesis, characterization, crystal structures, and anticancer activity of some new 2,3-dihydro-1,5-benzoxazepines

AbstractVarious benzoxazepine derivatives have been synthesized and characterized using IR, NMR, GC –MS, and microanalysis. The single-crystal X-ray structures of 2,2-dimethyl-4-[(E)-2-(4-methylphenyl)ethenyl]-2,3-dihydro-1,5-benzoxazepine (RS01),4-[(E)-2-(2-chlorophenyl)ethenyl] -2,2-dimethyl-2,3-dihydro-1,5-benzoxazepine (RS05),2,2,4-trimethyl-2,3-dihydrobenzothiazepine (RS11), and2,2,4-trimethyl-2,3-dihydrobenzoxazepine (RS12) have been discussed. The compounds have been evaluated for their anticancer properties in breast cancer cells.4-[(E)-2-(2-Chlorophenyl)ethenyl]-2,2-dimethyl-2,3-dihydro-1,5-benzoxazepine (RS03) andRS12 displayed potent cytotoxicity in both benign (MCF-7) and metastatic (MDA-MB-231) breast cancer cells. These compounds were more selective for the MCF-7 cells withRS03 being the most potent compound (IC50 = 15 µM) of the series. Upon further investigation, it was found thatRS03 andRS12 induced cell cycle arrest in the G2/M phase and display limited toxicity against the noncancerous breast cell line, MCF-10A.
Source: Medicinal Chemistry Research - Category: Chemistry Source Type: research