2-(Alkyl/Aryl)Amino-6-Benzylpyrimidin-4(3<i>H</i>)-ones as Inhibitors of Wild-Type and Mutant HIV-1: Enantioselectivity Studies

Abstract

The single enantiomers of two pyrimidine-based HIV-1 non-nucleoside reverse transcriptase inhibitors, <b>1</b> (MC1501) and <b>2</b> (MC2082), were tested in both cellular and enzyme assays. In general, the <i>R</i> forms were more potent than their <i>S</i> counterparts and racemates and (<i>R</i>)-<b>2</b> was more efficient than (<i>R</i>)-<b>1</b> and the reference compounds, with some exceptions. Interestingly, (<i>R</i>)-<b>2</b> displayed a faster binding to K103N RT with respect to WT RT, while (<i>R</i>)-<b>1</b> showed the opposite behavior