Convenient one-pot synthesis, anti-mycobacterial and anticancer activities of novel benzoxepinoisoxazolones and pyrazolones

Eur J Med Chem. 2014 Apr 9:76:460-9. doi: 10.1016/j.ejmech.2014.02.042.

G Saidachary ¹, K Veera Prasad ¹, D Divya ², Ashita Singh ², U Ramesh ², B Sridhar ³, B China Raju ⁴

Affiliations

1 Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
2 Center for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
3 Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
4 Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. Electronic address: chinaraju@iict.res.in.

PMID: 24607876 DOI: 10.1016/j.ejmech.2014.02.042

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.

Keywords

Anti-mycobacterial activity; Anticancer activity; Benzoxepinoisoxazolones; Benzoxepinopyrazolones; Cyclocondensation.

Name
Email *

	Sorry, but the email address you supplied was invalid.