Synthesis and anti-HIV activity of 4'-thio-2',3'-dideoxynucleosides.
A series of 2',3'-dideoxy-4'-thionucleoside analogues of purines and pyrimidines, including 4'-thioddI (17), 4'-thioddC (27), and 4'-thioAZT (34), were synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV). A stereospecific synthesis of the 2,3-dideoxy-4-thioribofuranosyl carbohydrate precursor 11 starting with L-glutamic acid is described. 2',3'-Dideoxy-4'-thiocytidine (27) displayed significant, but modest activity in vitro against human immunodeficiency virus.
Secrist
J A
JA
Kettering-Meyer Laboratory, Southern Research Institute, Birmingham, Alabama 35255-5305.
Riggs
R M
RM
Tiwari
K N
KN
Montgomery
J A
JA
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006678:HIV / Q000187:drug effects*
D000998:Antiviral Agents; D015224:Dideoxynucleosides