SYNTHESIS AND ANTIVIRAL EVALUATION OF FLUORINATED DIPYRIDODIAZEPINONES AND DIPYRIDODIAZEPINES (NEVIRAPINE DERIVATIVES)

The synthesis of trifluoromethyldipyridodiazepinones, which are analog ues of nevirapine, one of the nonnucleoside inhibitors of the HIV-1 RT enzyme, is described. The condensation of 3-amino-2-chloro-4-trifluor omethyl pyridine with 2-chloronicotinoyl chIoride followed by a cycliz ation with cyclopropyramine provided the corresponding trifluoromethyl ated dipyridodiazepinone. Similarly, the dipyridodiazepine analogues w ere synthesized by condensation of 3-amino-2-chloro-4-trifluoromethylp yridine with the O-mesyl derivative of 2-chloro-3-pyridincarbinol foll owed by reaction with cyclopropylamine, The inhibitory effect of these compounds on the HIV-1-induced cytopathic effect in MT4 cells has bee n evaluated.