Design, synthesis, in vitro antimicrobial and anticancer activity of novel methylenebis-isoxazolo[4,5-b]azepines derivatives

A series of novel methylene bis-isoxazolo[4,5-b]azepines have been synthesized by reaction of 3,5-dimethyl-4-nitroisoxazole 6 with an appropriate methylene bis-chalcones 7 to obtain various Michael adducts 8a–i, which on treatment with SnCl2–MeOH underwent reductive cyclization to afford the title compounds 9a–i. Structure of these compounds were established on the basis of IR, 1H NMR, 13C NMR and mass spectral data. The title compounds 9a–i were evaluated for their in vitro antimicrobial and anticancer activities. Compounds 9h and 9i exhibited potent antimicrobial and anticancer activities as that of standard drugs.

Graphical abstractSynthesis, in vitro antimicrobial and anticancer activity of novel methylene bis- isoxazolo[4,5-b]azepines (9a–i) have been reported.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Methylene-bis-isoxazolo[4,5-b]azepines have been synthesized from 3,5-dimethy-4-nitrolisoxazole by simple synthetic strategy. ► The title compounds have been evaluated for antimicrobial and anticancer activities. ► The tested compounds showed potent antimicrobial and anticancer activities as that of standard drugs.