title: Synthesis and in vitro and in vivo anticancer activity of novel phenylmethylene bis-isoxazolo[4,5-b]azepines.
abstract: A series of novel phenylmethylene bis-isoxazolo[4,5-b]azepine derivatives (10) have been synthesized from 3-methyl-4-nitro-5-styrylisoxazoles 6. The reaction of 6 with 3,5-dimethyl-4-nitroisoxazole (7) in piperidine afforded the Michael type adducts 8, which on treatment with different substituted chalcones in the presence of piperidine gave the Michael adducts 9. Compounds 9 underwent reductive cyclization on treatment with SnCl(2)-MeOH to afford the title compounds 10. Structure of these compounds was established on the basis of IR, (1)H NMR, (13)C NMR and Mass spectral data. The title compounds 10a-j were evaluated for in vitro and in vivo anticancer activity. Compound 10j exhibited good anticancer activity as that of standard drug Cisplatin.
authors.affiliation: Department of Chemistry, Kakatiya University, Warangal 506 009, AP, India. eligeti_rajan@yahoo.co.in
authors.forename: E
authors.initials: E
authors.lastname: Rajanarendar
authors.forename: M
authors.initials: M
authors.lastname: Nagi Reddy
authors.forename: K
authors.initials: K
authors.lastname: Rama Murthy
authors.forename: P
authors.initials: P
authors.lastname: Surendar
authors.forename: R N
authors.initials: RN
authors.lastname: Reddy
authors.forename: Y N
authors.initials: YN
authors.lastname: Reddy
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000494:pharmacology*; D001381:Azepines / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002945:Cisplatin / Q000494:pharmacology; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D066298:In Vitro Techniques; D020128:Inhibitory Concentration 50; D007555:Isoxazoles / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D000432:Methanol / Q000737:chemistry; D051379:Mice; D008956:Models, Chemical; D009369:Neoplasms / Q000188:drug therapy; D013055:Spectrophotometry, Infrared / Q000379:methods; D013778:Tetrazolium Salts / Q000494:pharmacology; D013844:Thiazoles / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D001381:Azepines; D007555:Isoxazoles; D013778:Tetrazolium Salts; D013844:Thiazoles; C022616:thiazolyl blue; D002945:Cisplatin; D000432:Methanol