Novel Heterocyclic Analogues of the HIV‐1 Protease Inhibitor, Ritonavir

Abstract

Hydroxyethylene dipeptide isosteres containing chromone, coumarin, chromene, and thiochromene moieties have been prepared as novel analogues of the human immunodeficiency virus (HIV)‐1 protease inhibitor, ritonavir.

Keywords:

• Chromone
• Coumarin
• Chromene
• Thiochromene
• HIV‐1 protease inhibitors

Acknowledgments

The authors thank the National Research Foundation (NRF)/Foundation for Research Development (FRD) for bursaries (to A. T. N. and X. W. N.), Rhodes University and the NRF/FRD for generous financial support and Mr A. Soper for assistance with NMR spectra.

Notes

^aAs determined by scoring different conformations of each compound to obtain the van der Waals protein–ligand interaction energies.

^bCompound 11 has also been obtained in 94% yield by alkaline hydrolysis of the nitrile 12; see Ref.27.