Synthesis and antimycobacterial activity of carbamate derivatives of 1,2-oxazine

Aseries of carbamate derivatives of 1,2-oxazine was obtained by means of [2 + 4]-cycloaddition of 1,3-dienes to C-nitroso-alkyl-N-arylcarbamates. The antimycobacterial activity of the synthesized compounds with respect to Mycobacterium tuberculosis and Mycobacterium lufu species was studied in vitro in comparison to isoniazid and dapsone. The activity of the newly synthesized compounds significantly depends on the nature and position of substituents in the oxazine nucleus and weakly depends on the nature of substituents in the carbamate moiety. Among the compounds tested, the maximum antimycobacterial activity was observed for 4,5-dimethyl-2-(p-methoxycarbonylamino)phenyl-3,6-dihydro-1,2-oxazine. __________ Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 40, No. 7, pp. 32–34, July, 2006.