Synthesis of benzo[b][1,4]oxazin-3(4H)-ones via smiles rearrangement for antimicrobial activity

Medicinal Chemistry Research (Impact Factor: 1.4). 07/2011; 20(6):670-677. DOI: 10.1007/s00044-010-9360-z


The benzo[b][1,4]oxazin-3(4H)-one derivs., e.g., I (R=-CH2Ph,cyclohexyl,hexyl) carrying F, Br, and Cl on the benzene ring, or benzyl, cyclohexyl, n-hexyl, and tetrafuryl methylene groups attached to nitrogen atom were synthesized via Smiles rearrangement and assayed in vitro for their antimicrobial activity against Gram-pos., Gram-neg. bacteria, and fungi. The antimicrobial activity of the benzo[b][1,4]oxazin-3(4H)-ones showed, on the whole, potency toward all the tested Gram-pos. and Gram-neg. microorganism (MIC ranging from 16 to 64 micro g/mL), whereas weak effectiveness was exhibited against fungi. Data obtained suggest that fluorine atom in the compds., I (R=-CH2Ph,cyclohexyl,hexyl) plays an important role in enhancing the antimicrobial properties of this class of compds. These observations provide some predictions to design further antimicrobial active compds. prior to their synthesis according to mol. modeling studies.

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