TSAO-T Analogues Bearing Amino Acids at Position N-3 of Thymine: Synthesis and Anti-Human Immunodeficiency Virus Activity
2000 ◽
Vol 11
(1)
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pp. 61-69
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Keyword(s):
Anti Hiv
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Novel analogues of the anti-HIV-1 lead compound [1-[2‘,5’-bis- O-( tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine]-3‘-spiro-5’-(4“-amino-1”,2“-oxathiole-2‘,2’-dioxide) (TSAO-T) bearing different amino acids at position N-3 of thymine were prepared and evaluated as inhibitors of HIV replication. The synthesis of the target compounds was accomplished by coupling of the appropriate TSAO intermediate with a conveniently protected (L) amino acid in the presence of BOP and triethylamine, followed by depro-tection of the amino acid moiety. Several TSAO derivatives, bearing at N-3 position of the thymine base an L-amino acid retaining the free carboxylic acid, acquired activity against HIV-2, in addition to their inhibitory effect on HIV-1.
1996 ◽
Vol 7
(1)
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pp. 31-36
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Keyword(s):
1987 ◽
Vol 42
(9)
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pp. 1167-1173
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Keyword(s):
2001 ◽
Vol 75
(21)
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pp. 10479-10487
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1999 ◽
Vol 73
(4)
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pp. 2781-2789
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Keyword(s):
2001 ◽
Vol 45
(4)
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pp. 1225-1230
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1997 ◽
Vol 185
(5)
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pp. 805-816
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2002 ◽
Vol 76
(18)
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pp. 9143-9151
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Keyword(s):