Conformational preferences of non-nucleoside HIV-1 reverse transcriptase inhibitors

The non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTI) are a class of compounds that present a common butterfly-like conformation. In the present study, the intramolecular factors that contribute to this conformation were studied. Hydrogen bonds have been analysed by geometric and electrostatic criteria. Only the former allow the elucidation of the relative intensity of hydrogen bonds. The interaction between aromatic rings may contribute to the preferential conformation. For some other NNRTI, it is not possible to explain the butterfly-like conformation on the basis of hydrogen bond and aromatic interactions.