Discovery and Pre-Clinical Characterization of Third-Generation 4-H Heteroaryldihydropyrimidine (HAP) Analogues as Hepatitis B Virus (HBV) Capsid Inhibitors

J Med Chem. 2017 Apr 27;60(8):3352-3371. doi: 10.1021/acs.jmedchem.7b00083. Epub 2017 Apr 5.

Abstract

Described herein are the discovery and structure-activity relationship (SAR) studies of the third-generation 4-H heteroaryldihydropyrimidines (4-H HAPs) featuring the introduction of a C6 carboxyl group as novel HBV capsid inhibitors. This new series of 4-H HAPs showed improved anti-HBV activity and better drug-like properties compared to the first- and second-generation 4-H HAPs. X-ray crystallographic study of analogue 12 (HAP_R01) with Cp149 Y132A mutant hexamer clearly elucidated the role of C6 carboxyl group played for the increased binding affinity, which formed strong hydrogen bonding interactions with capsid protein and coordinated waters. The representative analogue 10 (HAP_R10) was extensively characterized in vitro (ADMET) and in vivo (mouse PK and PD) and subsequently selected for further development as oral anti-HBV infection agent.

MeSH terms

  • Animals
  • Capsid / drug effects*
  • Crystallography, X-Ray
  • Drug Discovery
  • Hep G2 Cells
  • Hepatitis B virus / drug effects*
  • Humans
  • Mass Spectrometry
  • Mice
  • Proton Magnetic Resonance Spectroscopy
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacokinetics
  • Pyrimidines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Pyrimidines