141684-47-1Relevant articles and documents
Synthesis of 3' '-substituted TSAO derivatives with anti-HIV-1 and anti-HIV-2 activity through an efficient palladium-catalyzed cross-coupling approach.
Lobaton, Esther,Rodriguez-Barrios, Fatima,Gago, Federico,Perez-Perez, Maria-Jesus,De Clercq, Erik,Balzarini, Jan,Camarasa, Maria-Jose,Velazquez, Sonsoles
, p. 3934 - 3945 (2002)
Various synthetic studies for the introduction of several functional groups at position 3' ' of the spiro moiety of TSAO derivatives have been explored. Among them, Stille cross-coupling of 3' '-iodo-TSAO derivatives with different stannanes provided an e
3'-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors: Synthesis and antiviral activity of [2',5'-bis-O-(tert- butyldimethylsilyl)-β-D-xylo- and -ribofuranose]-3'-spiro-5''-[4''-amino- 1'',2''-oxathiole 2'',2''-dioxide] (TSAO) pyrimidine nucleosides
Camarasa,Perez-Perez,San-Felix,Balzarini,De Clercq
, p. 2721 - 2727 (2007/10/02)
A series of 3'-spiro nucleosides have been synthesized and evaluated as anti-HIV-1 agents. Reaction of O-mesyl-cyanohydrins of furanos-3'-ulosyl nucleosides with base afforded [1,[2',5'-bis-O-(tert-butyldimethylsilyl)-β- D-xylo- and -ribofuranosyl]]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole 2'',2''-dioxide] derivatives of thymine, uracil and 4-N-acetylcytosine 11 and 12. Desilylation of 11 and 12 gave the full deprotected 3'-spiro xylo- and ribofuranosyl nucleosides 13 and 14 or the partially 5'-O-deprotected-3'- spiro β-D-xylo- and -ribo-nucleosides 15 and 16, or 2'-O-deprotected-3'- spiro β-D-ribo-nucleoside 17. 2'-Deoxygenation of 17 afforded 2'-deoxy-3'- spiro β-D-erythro-pentofuranosyl derivative 18. These 3'-spiro derivatives were evaluated for their anti-HIV-1 activity. All 3'-spiro nucleosides having a xylo configuration did not show any anti-HIV-1 activity. 3'-Spiro ribo- nucleosides with none or only one silyl group at C-2' or C-5' or the 2'-deoxy derivative were also inactive at subtoxic concentrations. However, 3'-spiro ribo-nucleosides having two silyl groups at C-2' and C-5' were potent and selective inhibitors of HIV-1. None of the nucleoside analogues that showed anti-HIV-1 activity proved inhibitory to the replication of HIV-2 or SIV.