5-Alkyl- and 5-alkenyl-uracil and -cytidine nucleoside derivs. - prepd. e.g. by reaction of 5'-chloro-5'-deoxy cpds. with ammonia

摘要

New 5-alkyl- and 5-alkenyl-pyrinidine nucleoside derivs. are cpds. of formula (I): (where R is NH2 or OH, R1 is 2-8C alkyl or alkenyl opt. substd. by an F, Cl, Br or I atom, R2 is H or Cl, R3 is H or OH, R4 is OH, NH2 or -O-NO2, R5 is -OH, -OSO2-NH2, -NH2, -NH-SO3H, -NHR' or -NH-CX-NHR2, R' is 3-6C alkyl, X is O or S, and R2 is 1-6C alkyl, F or Cl). ( Cpds. in which R is NH2 may be prepd. from corresponding N-protected 5-alkyl-cytidine derivs. by (a) reaction with SOCl2 to give the 5'-chloro-5'-deoxy cpds., and (b) either reaction of the 5'-chloro cpds. with NH2 or reaction of the 5'-chloro cpds. with an azide and reduction of the resulting 5'-azido-5'-deoxy cpd. Cpds. in which R4 is -ONO2 may be prepd. by reaction of corresponding hydroxy cpds. with nitric acid. (I) have virustatic activity and also have marked cytostatic activity. Thus, (I) strongly inhibit the development of Ehrlich ascites tumour in mice. (I) may be administered orally, parenterally or locally.