Biphenyl/diphenyl ether renin inhibitors: filling the S1 pocket of renin via the S3 pocket

Bioorg Med Chem Lett. 2011 Aug 15;21(16):4836-43. doi: 10.1016/j.bmcl.2011.06.043. Epub 2011 Jun 17.

Abstract

Structure-based design led to the discovery of a novel class of renin inhibitors in which an unprecedented phenyl ring filling the S1 site is attached to the phenyl ring filling the S3 pocket. Optimization for several parameters including potency in the presence of human plasma, selectivity against CYP3A4 inhibition and improved rat oral bioavailability led to the identification of 8d which demonstrated antihypertensive efficacy in a transgenic rat model of human hypertension.

MeSH terms

  • Animals
  • Antihypertensive Agents / chemical synthesis
  • Antihypertensive Agents / chemistry
  • Antihypertensive Agents / pharmacology*
  • Biological Availability
  • Crystallography, X-Ray
  • Cytochrome P-450 CYP3A / blood
  • Cytochrome P-450 CYP3A Inhibitors
  • Disease Models, Animal
  • Dose-Response Relationship, Drug
  • Drug Discovery
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Hypertension / drug therapy
  • Models, Molecular
  • Molecular Conformation
  • Phenyl Ethers / chemical synthesis
  • Phenyl Ethers / chemistry
  • Phenyl Ethers / pharmacology*
  • Rats
  • Rats, Transgenic
  • Recombinant Proteins / antagonists & inhibitors
  • Recombinant Proteins / isolation & purification
  • Renin / antagonists & inhibitors*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antihypertensive Agents
  • Cytochrome P-450 CYP3A Inhibitors
  • Enzyme Inhibitors
  • Phenyl Ethers
  • Recombinant Proteins
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human
  • Renin