Journal of Heterocyclic Chemistry p. 177 - 185 (1994)
Update date:2022-09-26
Topics:
Pan
Chen
Piras
Dutschman
Rowe
Cheng
Chu -
6-Arylthio and 6-arylselenoacyclonucleosides was synthesized and tested for the ability to inhibit replication of HIV-1. Lithiation of acyclonucleosides with LDA followed by reaction with the electrophiles phenyl disulfide, diphenyl diselenide, 2,2'-dipyrdyl disulfide or 2,2'-dipyridyl diselenide afforded 6-(arylthio or arylseleno)acyclonucleosides 5a-c, 6, 7, 9, 15a-c, 17a-c. Compounds 19a-c and 20a-c were obtained by deprotection of corresponding TBDMS derivatives. Dehydrated products 16a, and 18a-c were also formed during the reactions. 5-Ethyl-6-(α-pyridylthio or α-pyridylseleno) disubstituted acyclouracils 6 and 7 were more active against HIV-1 in both MT-2 and CEM-IW cell lines than AZT, DDC, DDI or D4T. The EC50 of 6 against HIV-1 in CEM-IW cell was in the nanomolar range with a therapeutic index of 1100.
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