Uncharged AZT and D4T Derivatives of Phosphonoformic and Phosphonoacetic Acids as Anti-HIV Pronucleosides
- 29 May 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 47 (14), 3606-3614
- https://doi.org/10.1021/jm0310176
Abstract
Two series of new lipophilic phosphonoformate and phosphonoacetate derivatives of AZT and d4T were synthesized and evaluated as anti-HIV agents. The efficacy of some of the synthesized compounds in cell cultures infected with HIV-1 was higher than that of the parent nucleosides and only slightly correlated to their stability in the phosphate buffer and human blood serum. The synthesized phosphonates are most probably prodrug forms of the corresponding nucleosides.Keywords
This publication has 11 references indexed in Scilit:
- Synthesis and Antiherpetic Activity of Acyclovir PhosphonatesNucleosides, Nucleotides and Nucleic Acids, 2003
- Ether Phospholipid-AZT Conjugates Possessing Anti-HIV and Antitumor Cell Activity. Synthesis, Conformational Analysis, and Study of Their Thermal Effects on Membrane BilayersJournal of Medicinal Chemistry, 2001
- Cyclosaligenyl-2′,3′-didehydro-2′,3′-dideoxythymidine Monophosphate: Efficient Intracellular Delivery of d4TMPMolecular Pharmacology, 2000
- Pronucleotides: Toward thein vivo delivery of antiviral and anticancer nucleotidesMedicinal Research Reviews, 2000
- Synthesis and anti-HIV activity of some novel arylphosphate and H-phosphonate derivatives of 3′-azido-2′,3′-dideoxythymidine and 2′,3′-didehydro-2′,3′-dideoxythymidineAntiviral Research, 1999
- Antiviral Activity and Resistance Profile of Phosphazid - A Novel Prodrug of AZTNucleosides, Nucleotides and Nucleic Acids, 1999
- 5′-Phosphonates of Ribonucleosides and 2′-Deoxyribonucleosides: Synthesis and Antiviral ActivityNucleosides and Nucleotides, 1993
- Synthesis of N-thietan-3-yl-.alpha.-oxo nitrogen heterocycles from iminothioethers. A novel transformationThe Journal of Organic Chemistry, 1992
- Synthesis and antiviral activity of phosphonoacetic and phosphonoformic acid esters of 5-bromo-2'-deoxyuridine and related pyrimidine nucleosides and acyclonucleosidesJournal of Medicinal Chemistry, 1989
- Synthesis of esters of phosphonoformic acid and their antiherpes activityJournal of Medicinal Chemistry, 1983