Carbocyclic analogs of 5'-amino-5'deoxy- and 3'-amino-3'-deoxythymidines

Abstract

The carbocyclic analogue of 5''-amino-5''-deoxythymidine was synthesized from the carbocyclic analogue of 2,5''-O-anhydrothymidine acetate. The carbocyclic analogues of 3''-amino-3''-deoxythymidine and of 1-(3''-amino-2'',3''-dideoxylyxofuranosyl)thymidine (an all-cis structure) were synthesized from the carbocyclic analogues of 5''-O-trityl-2,3''-0-anhydrothymidine and 5''-O-trityl-3''-O-(methylsulfonyl)thymidine, respectively. The carbocyclic analogue of 5''-amino-5''-deoxythymidine inhibited cytopathogenic effects (CPE) induced by a TK+ strain of type 1 herpes simplex virus replicating in L929 (mouse connective tissue) cells, but it did not inhibit CPE in Vero cells. In contrast, the all-cis-3''-azido-3''-deoxythymidine analogue demonstrated modest inhibition of CPE in Vero cells, but not in L929 cells.