Design and synthesis of novel sulfonamide-containing bradykinin hB(2) receptor antagonists. Synthesis and structure-relationships of α,α-tetrahydropyranylglycine

Bioorg Med Chem. 2012 Mar 15;20(6):2091-100. doi: 10.1016/j.bmc.2012.01.036. Epub 2012 Jan 30.

Abstract

A series of α,α-cycloalkylglycine sulfonamide compounds of general formula 1 has previously been identified by our group as selective human B(2)(hB(2)) receptor antagonists. Here we report the in vitro and in vivo BK antagonist activity of a further evolution of the series, consisting in compounds of the general formula 2, containing either an alkyl piperazine or a 4-alkyl piperidine ring bearing various positively charged groups (R'). These studies unexpectedly revealed quite a flat nanomolar/subnanomolar SAR for the binding affinity, while differences were seen in the in vitro functional activities. We propose that variations in the residence time may explain these results.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bradykinin / metabolism
  • Bradykinin B2 Receptor Antagonists*
  • Bronchoconstriction / drug effects
  • CHO Cells
  • Cricetinae
  • Glycine / analogs & derivatives*
  • Glycine / chemical synthesis
  • Glycine / pharmacology*
  • Guinea Pigs
  • Humans
  • Hypotension / drug therapy
  • Receptor, Bradykinin B2 / metabolism
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacology*

Substances

  • Bradykinin B2 Receptor Antagonists
  • Receptor, Bradykinin B2
  • Sulfonamides
  • Bradykinin
  • Glycine