Effects of Aryl Substituents on the Anti-HIV Activity of the Arylphosphoramidate Derivatives of Stavudine-Reference-Cited by-同舟云学术

Effects of Aryl Substituents on the Anti-HIV Activity of the Arylphosphoramidate Derivatives of Stavudine

Published:2002-06 Issue:3 Volume:13 Page:197-203
ISSN:2040-2066
Container-title:Antiviral Chemistry and Chemotherapy
language:en
Short-container-title:Antivir Chem Chemother

Author:

Uckun Fatih M¹,Samuel P²,Qazi S³,Chen C²,Pendergrass S¹,Venkatachalam TK⁴

Affiliation:

1. Department of Virology, Parker Hughes Cancer Center, Parker Hughes Institute St. Paul, Minn., USA

2. Department of Pharmaceutical Sciences, Parker Hughes Cancer Center, Parker Hughes Institute St. Paul, Minn., USA

3. Department of Bioinformatics, Parker Hughes Cancer Center, Parker Hughes Institute St. Paul, Minn., USA

4. Departments of Chemistry, Drug Discovery Program, Parker Hughes Cancer Center, Parker Hughes Institute St. Paul, Minn., USA

Abstract

We compared the anti-HIV activity of 13 phenyl phosphate derivatives of stavudine (2′,3′-didehydro-2′,3′-dideoxythymidine/d4T) by examining their ability to inhibit HIV-1 replication in human peripheral blood mononuclear cells. Our results show that the introduction of electron-withdrawing substituents enhances the activity of these phosphoramidate derivatives. The rate of chemical hydrolysis under alkaline conditions (but not the lipophilicity) predicted the potency of the compounds.

Publisher

SAGE Publications

Link

http://journals.sagepub.com/doi/pdf/10.1177/095632020201300306

Reference8 articles.

1. The Molecular Biology of Human Immunodeficiency Virus Type 1 Infection

2. Probing the Mechanism of Action and Decomposition of Amino Acid Phosphomonoester Amidates of Antiviral Nucleoside Prodrugs

3. AIDS — The First 20 Years

4. Design and Synthesis of Lipophilic Phosphoramidate d4T-MP Prodrugs Expressing High Potency Against HIV in Cell Culture: Structural Determinants for in Vitro Activity and QSAR

Cited by 17 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. With DBU-activated N-bromophthalimide as potential N-sources to achieve P–N cross-coupling of P(O)–H compounds;Tetrahedron Letters;2016-06

2. Iodine catalyzed solvent-free cross-dehydrogenative coupling of arylamines and H-phosphonates for the synthesis of N-arylphosphoramidates under atmospheric conditions;Tetrahedron Letters;2014-02

3. Copper-catalyzed aerobic oxidative cross-coupling of arylamines and dialkylphosphites leading to N-arylphosphoramidates;Tetrahedron Letters;2013-11

4. WITHDRAWN: Efficient transformation of nitroarenes into dialkyl N-arylphosphoramidates in one step under microwave conditions;Tetrahedron;2012-10

5. Practical and reliable synthesis of dialkyl N-arylphosphoramidates with nitroarenes as substrates;Tetrahedron Letters;2009-12