New Phosphonate Analogues of 3′-Thia-2′,3′-dideoxycytidine(BCH-189) Synthesis and Anti-HIV Evaluation

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Abstract
New phosphonate analogues of 3′-thia-2′,3′-dideoxycytidine (BCH-189) were synthesized in 5 steps via cyclocondensation of 2-mercaptoacetaldehyde di[2-methoxyethyl]acetal with 3-diethylphosphonopropionaldehyde as a key step, followed by a Lewis acid catalyst addition of the appropriate nucleic base. Anti-HIV evaluation of these analogues showed that the α-form 3b of 3′-thia-2′,3′-dideoxycytidine-4′-ethylene phosphonic acid was inactive while the β-form 3a was found to be less potent than the parent compound (BCH-189), showing that the replacement of the oxygen in position 5′ by a methylene group in the monophosphorylated intermediate diminishes the antiviral activity.

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