Discovery of macrocyclic covalent inhibitors for severe acute respiratory syndrome coronavirus 2 3CL protease

Bioorg Med Chem. 2024 Sep 1:111:117846. doi: 10.1016/j.bmc.2024.117846. Epub 2024 Jul 22.

Abstract

The coronavirus disease caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has been spread worldwide for more than 3 years. Although the hospitalization rate and mortality have decreased dramatically due to wide vaccination effort and improved treatment options, the disease is still a global health issue due to constant viral mutations, causing negative impact on social and economic activities. In addition, long COVID and complications arising from COVID-19 weeks after infection have become a concern for public health experts. Therefore, better treatments for COVID-19 are still needed. Herein, we describe a class of macrocyclic peptidomimetic compounds that are potent inhibitors of SARS-Cov-2 3CL protease (3CLpro). Significantly, some of the compounds showed a higher stability against human liver microsomes (HLM t1/2 > 180 min) and may be suitable for oral administration without the need for a pharmacokinetic (PK) boosting agent such as ritonavir.

Keywords: 3CL(pro); Covalent inhibition; Macrocyclization; SARS-CoV-2.

MeSH terms

  • Antiviral Agents* / chemical synthesis
  • Antiviral Agents* / chemistry
  • Antiviral Agents* / pharmacokinetics
  • Antiviral Agents* / pharmacology
  • COVID-19 Drug Treatment
  • Coronavirus 3C Proteases* / antagonists & inhibitors
  • Coronavirus 3C Proteases* / metabolism
  • Drug Discovery
  • Humans
  • Macrocyclic Compounds* / chemical synthesis
  • Macrocyclic Compounds* / chemistry
  • Macrocyclic Compounds* / pharmacokinetics
  • Macrocyclic Compounds* / pharmacology
  • Microsomes, Liver / metabolism
  • Peptidomimetics / chemical synthesis
  • Peptidomimetics / chemistry
  • Peptidomimetics / pharmacology
  • Protease Inhibitors / chemical synthesis
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacokinetics
  • Protease Inhibitors / pharmacology
  • SARS-CoV-2* / drug effects
  • Structure-Activity Relationship

Substances

  • Coronavirus 3C Proteases
  • Macrocyclic Compounds
  • Antiviral Agents
  • 3C-like proteinase, SARS-CoV-2
  • Peptidomimetics
  • Protease Inhibitors