Pyrrolidine-5,5-trans-lactams. 2. The use of X-ray crystal structure data in the optimization of P3 and P4 substituents

Org Lett. 2002 Dec 12;4(25):4479-82. doi: 10.1021/ol027014p.

Abstract

[reaction: see text] In this, the second of two letters, we describe the elaboration of the pyrrolidine-5,5-trans-lactam template to delineate the requirements for optimal substitution of the pyrrolidine and lactam nitrogen atoms. Central to the strategy is the use of rapid iterative synthesis in conjunction with X-ray crystal structure determination of ligand-protein complexes.

MeSH terms

  • Cell Line
  • Crystallography, X-Ray
  • Drug Design*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Hepacivirus / drug effects
  • Hepacivirus / enzymology
  • Inhibitory Concentration 50
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Lactams / pharmacology
  • Models, Molecular
  • Molecular Structure
  • Protein Conformation
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Pyrrolidines / pharmacology
  • Viral Nonstructural Proteins / antagonists & inhibitors*
  • Viral Nonstructural Proteins / chemistry*
  • Viral Nonstructural Proteins / metabolism

Substances

  • Enzyme Inhibitors
  • Lactams
  • NS3 protein, hepatitis C virus
  • Pyrrolidines
  • Viral Nonstructural Proteins