Toward nonpeptidal substance P mimetic analogues: design, synthesis, and biological activity

Biopolymers. 1991 May;31(6):725-33. doi: 10.1002/bip.360310617.

Abstract

1,4-Piperazine and 4-hydroxyproline, two small cyclic polyfunctional systems with defined stereochemistry, were introduced as "molecular scaffolds." We define a "bioactive topology," which is a derived putative low-energy conformation obtained through theoretical conformational analysis of substance P. Substitution of these molecular scaffolds by pharmacophors characteristic of the bioactive topology of the C-terminal hexapeptide of substance P resulted in active, partially nonpeptidal substance P mimetic agonists. The study discusses the concepts and tools used to achieve this structural transformation, and points out the need to address flexibility-rigidity issues in an attempt to maintain sufficient molecular plasticity.

MeSH terms

  • Amino Acid Sequence
  • Drug Design
  • Hydroxyproline / chemistry
  • Molecular Sequence Data
  • Molecular Structure
  • Piperazine
  • Piperazines
  • Protein Conformation
  • Sequence Homology, Nucleic Acid
  • Substance P / analogs & derivatives*
  • Substance P / chemical synthesis
  • Substance P / chemistry
  • Substance P / metabolism

Substances

  • Piperazines
  • Piperazine
  • Substance P
  • Hydroxyproline