Synthesis, Anti-HIV Activity and Stability Studies of 3′-Azido-2′,3′-dideoxythymidine-5′-fluorophosphate

• Published in: Nucleosides & nucleotides Vol. 18; no. 4-5; pp. 983 - 984
• Main Authors: Egron, D., Arzumanov, A. A., Dyatkina, N. B., Krayevsky, A., Imbach, J-L., Aubertin, A-M., Gosselin, G., Périgaud, C.
• Format: Journal Article
• Language: English
• Published: United States Taylor & Francis Group 01.04.1999
• Subjects: AIDS/HIV; Anti-HIV Agents - chemical synthesis; Anti-HIV Agents - chemistry; Anti-HIV Agents - pharmacology; Cell Line; Dideoxynucleotides; Fluorine - chemistry; HIV-1 - drug effects; HIV-1 - physiology; Humans; Thymine Nucleotides - chemical synthesis; Thymine Nucleotides - chemistry; Thymine Nucleotides - pharmacology; Virus Replication - drug effects; Zidovudine - analogs & derivatives; Zidovudine - chemical synthesis; Zidovudine - chemistry; Zidovudine - pharmacology
• ISSN: 0732-8311; 2332-3892
• DOI: 10.1080/15257779908041621

The synthesis, in vitro anti-HIV activity, and stability studies of AZT 5′-fluorophosphate (F-AZTMP) are reported. The present results demonstrate that such compound is a bioprecursor of its parent 5′-mononucleotide (AZTMP) but its biotransformation does not allow its selective intracellular delivery. Moreover, several attempts were carried out in order to improve the biological activity of this compound by the use of a SATE prodrug strategy.