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Synthesis 2004(11): 1874-1878
DOI: 10.1055/s-2004-829137
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
Further Information
Publication History
Received
2 April 2004
Publication Date:
01 July 2004 (online)


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