Synthesis of AZT/d4T boranophosphates as anti-HIV prodrug candidates
AZT/d4T phosphonates were synthesized by sequential condensation of AZT/ d4T with the corresponding alcohols or 5′-DMT-thymidine in the presence of pivaloyl chloride. Sequential silylation, boronation, and hydrolysis in ammonium hydroxide of these phosphonates led to anti-HIV prodrug candidates AZT/d4T boranophosphates.
Lin, Changxue,Fu, Hua,Tu, Guangzhong,Zhao, Yufen
p. 509 - 516
(2007/10/03)
One-pot synthesis of hydrogen phosphonate derivatives of d4T and AZT.
A simple and one-pot route for the synthesis of d4T or AZT hydrogen phosphonate derivatives via reaction of d4T or AZT with phosphorus trichloride, then alcoholysis and dealkylation in the presence of the corresponding alcohol is described.
Sun, Xiao Bin,Kang, Jian Xun,Zhao, Yu Fen
p. 2414 - 2415
(2007/10/03)
P-(Alkyl)-nucleoside 5′-hydrogenphosphonates as depot forms of antiviral nucleotide analogues
P-(Alkyl)esters of AZT 5′-hydrogenphosphonate were synthesized and their stabilities in the phosphate buffer and human serum were evaluated. The esters bearing residues of primary and secondary alcohols were degraded to give AZT, whereas those containing tertiary alkyl groups yielded AZT 5′-hydrogenphosphonate. The corresponding derivatives of d2A and d2T showed the same properties.