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

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'-di-deoxylyxofuranosyl)thymine (an all-cis structure) were synthesized from the carbocyclic analogues of 5'-O-trityl-2,3'-O-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.