Preliminary SAR and biological evaluation of potent HIV-1 protease inhibitors with pyrimidine bases as novel P2 ligands to enhance activity against DRV-resistant HIV-1 variants

  • Eur J Med Chem. 2020 Jan 1;185:111866. doi: 10.1016/j.ejmech.2019.111866.
Mei Zhu  1 Ling Ma  1 Huiyu Zhou  1 Biao Dong  1 Yujia Wang  1 Zhen Wang  2 Jinming Zhou  1 Guoning Zhang  1 Juxian Wang  1 Chen Liang  2 Shan Cen  3 Yucheng Wang  4
Affiliations
  • 1. Institute of Medicinal Biotechnology, Chinese Academy of Medical Science and Peking Union Medical College, Beijing, 100050, China.
  • 2. Lady Davis Institute for Medical Research and McGill AIDS Centre, Jewish General Hospital, Montreal, Quebec, Canada.
  • 3. Institute of Medicinal Biotechnology, Chinese Academy of Medical Science and Peking Union Medical College, Beijing, 100050, China. Electronic address: [email protected].
  • 4. Institute of Medicinal Biotechnology, Chinese Academy of Medical Science and Peking Union Medical College, Beijing, 100050, China. Electronic address: [email protected].
Abstract

Introducing pyrimidine Bases, the basic components of nucleic acid, to P2 ligands might enhance the potency of Human Immunodeficiency Virus-1 (HIV-1) Protease Inhibitors because of the carbonyl and amino groups promoting the formation of extensive hydrogen bonding interactions. In this work, we provide evidence that inhibitor 10e, with N-2-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl) acetamide as the P2 ligand and a 4-methoxylphenylsulfonamide as the P2' ligand, displayed remarkable enzyme inhibitory and Antiviral activity, with the IC50 2.53 nM in vitro and a promising inhibition ratio with 68% against wild-type HIV-1 in vivo, with low cytotoxicity. This inhibitor also exhibited appreciable Antiviral activity against DRV-resistant HIV-1 variants, which was of great value for further study.

Keywords
Antiviral activity; DRV-Resistant HIV-1 variants; HIV-1 protease inhibitors; Pyrimidine bases.
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