Synthesis and antiviral activity of amino acid carbamate derivatives of AZT

Article abstract of DOI:10.1080/15257770008032998

Lipophilic amino acid methyl ester and methyl amide carbamates of 3'- azido-3'-deoxythymidine (AZT) were synthesized and their anti-HIV-1 activity in PBMCs was determined. The methyl amides were more potent (EC₅₀s = 1.8 - 4.0 μM) than the methyl esters (EC₅₀s = 2.0 - 20 μM). Carbamate hydrolysis by cell lysates and liberation of AZT was not observed for representative methyl ester or methyl amide AZT carbamates. No evidence of direct inhibition of HIV reverse transcriptase or integrase was observed.

Full text of DOI:10.1080/15257770008032998

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Nucleosides, Nucleotides and Nucleic
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Synthesis and Antiviral Activity of Amino
Acid Carbamate Derivatives of AZT
Shu-Ling Chang a c , George Griesgraber a , Timothy W. Abraham a
Tullika Garg a , Heng Song b , Cheryl L. Zimmerman b & Carston R.
Wagner a c
,
a Departments of Medicinal Chemistry College of Pharmacy,
University of Minnesota, Minneapolis, MN, 55455, USA
b Departments of Pharmaceutics College of Pharmacy, University of
Minnesota, Minneapolis, MN, 55455, USA
c Departments of Program in Microbiology, Immunology and
Molecular Pathobiology College of Pharmacy, University of
Minnesota, Minneapolis, MN, 55455, USA
Version of record first published: 24 Sep 2006
To cite this article: Shu-Ling Chang, George Griesgraber, Timothy W. Abraham, Tullika Garg, Heng
Song, Cheryl L. Zimmerman & Carston R. Wagner (2000): Synthesis and Antiviral Activity of Amino
Acid Carbamate Derivatives of AZT, Nucleosides, Nucleotides and Nucleic Acids, 19:1-2, 87-100
To link to this article: http://dx.doi.org/10.1080/15257770008032998
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