Synthesis and biological activity of several amino analogs of thymidine

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Abstract
3'',5''-Diamino-3'',5''-dideoxythymidine (7) was synthesized via a 9-step synthesis from thymidine in good overall yield. 3''-Amino-3''-deoxythymidine (8) and 5''-amino-5''-deoxythymidine (12) were prepared with a minor modification of the procedure reported by Horwitz and co-workers. Although the 5''-amino analogue 12 had potent antiviral activity relative to the 3''-amino analogue 8, the latter is a potent inhibitor of the replication of murine sarcoma 180 cells (ED50 = 5 .mu.M) and of murine L1210 cells (ED50 = 1 .mu.M) in vitro. Most unexpectedly was the finding of complete lack of antiviral or antineoplastic activity by the 3'',5''-diamino analogue 7 which appears to have acquired undesirable qualities of the 3''-amino and 5''-amino analogues of thymidine.