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Synthesis 2004(11): 1874-1878  
DOI: 10.1055/s-2004-829137
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-1-Alkylated 6-Benzyluracil-5-carboxylic Esters as Potential Non-Nucleoside Reverse Transcriptase Inhibitors

Janus S. Larsena, Erik B. Pedersen*a, Claus Nielsenb
a Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, Campusvej 55, 5230 Odense M, Denmark
Fax: +4566158780; e-Mail: ebp@chem.sdu.dk ;
b Retrovirus Laboratory, Department of Virology, State Serum Institute, Artillerivej 5, 2300 Copenhagen, Denmark
Further Information

Publication History

Received 2 April 2004
Publication Date:
01 July 2004 (online)

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Abstract

A series of N-1-alkylated 6-benzyluracil-5-carboxylic esters 4a-h were synthesized by reacting imines of 3-oxo-4-phenylbutyrates with N-(chlorocarbonyl) isocyanate. An N-1-(4-methoxybenzyl) group could be removed in a dealkylation reaction to give the ethyl and allyl esters 5a and 5b, respectively. They were N-1-alkylated with chloromethyl ethyl ether or dialloxymethane. Unfortunately no biological activity against HIV-1 and HSV was observed for any of the synthesized compounds.

Key words

HIV-1 - HSV - non-nucleoside reverse transcriptase inhibitors - uracil-5-carboxylic esters - Emivirine

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