Synthesis and evaluation of new potential HIV-1 non-nucleoside reverse transcriptase inhibitors. New analogues of MKC-442 containing Michael acceptors in the C-6 …

L Petersen, CH Jessen, EB Pedersen…

Index: Petersen, Lene; Jessen, Carsten H.; Pedersen, Erik B.; Nielsen, Claus Organic and Biomolecular Chemistry, 2003 , vol. 1, # 20 p. 3541 - 3545

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Citation Number: 9

Abstract

Analogues of MKC-442 capable of undergoing Michael addition reactions were synthesised in order to investigate the activity against the HIV-1 mutant (Y181C). An improved activity was postulated on the basis of a possible covalent binding to the mercapto group of Cys181. Lithiation of the C-6 position of 1-ethoxymethyl-5-ethyl-1H-pyrimidine-2, 4-dione (5) was followed by reaction with α, β-unsaturated aldehydes and oxidation of the alcohols formed ...