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Synthesis and anti-HIV activity of 4'-thio-2',3'-dideoxynucleosides
J A Secrist1, R M Riggs, K N Tiwari
1Kettering-Meyer Laboratory, Southern Research Institute, Birmingham, Alabama 35255-5305.
Journal of Medicinal Chemistry
|February 7, 1992
Abstract:
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.