title: Convenient one-pot synthesis, anti-mycobacterial and anticancer activities of novel benzoxepinoisoxazolones and pyrazolones.
abstract: Series of new benzoxepinoisoxazolones 4a-d and pyrazolones 6a-t were prepared by the cyclocondensation of substituted (E)-ethyl 3-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates 3a-d with hydroxylamine hydrochloride and phenylhydrazine hydrochlorides 5a-k. Synthesized compounds were screened for their in vitro anti-mycobacterial activity and anticancer activity. Ten compounds displayed good anti-mycobacterial activity, among these; compound 4d and 6b found to be potent when compared to standard drug isoniazid. Eleven compounds displayed good anticancer activity and compounds 4b-d displayed equipotent activity on HeLa cell lines when compared to standard drug doxorubicin. Activation of caspase-3 and caspase-9 has been measured for compounds 4b-d on HeLa cell lines (apoptosis). This is the first report assigning in vitro anti-mycobacterial, anticancer and structure-activity relationship for this new class of benzoxepinoisoxazolones and pyrazolones.
authors.affiliation: Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: G
authors.initials: G
authors.lastname: Saidachary
authors.affiliation: Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: K
authors.initials: K
authors.lastname: Veera Prasad
authors.affiliation: Center for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: D
authors.initials: D
authors.lastname: Divya
authors.affiliation: Center for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: Ashita
authors.initials: A
authors.lastname: Singh
authors.affiliation: Center for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: U
authors.initials: U
authors.lastname: Ramesh
authors.affiliation: Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: B
authors.initials: B
authors.lastname: Sridhar
authors.affiliation: Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. Electronic address: chinaraju@iict.res.in.
authors.forename: B
authors.initials: B
authors.lastname: China Raju
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001584:Benzoxepins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D047069:Pyrazolones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
chemical_list: D000970:Antineoplastic Agents; D000995:Antitubercular Agents; D001584:Benzoxepins; D047069:Pyrazolones
keywords: Anti-mycobacterial activity; Anticancer activity; Benzoxepinoisoxazolones; Benzoxepinopyrazolones; Cyclocondensation