α-Adrenoceptor antagonistic and hypotensive properties of novel arylpiperazine derivatives of pyrrolidin-2-one

Bioorg Med Chem. 2015 May 1;23(9):2104-11. doi: 10.1016/j.bmc.2015.03.009. Epub 2015 Mar 9.

Abstract

This study focused on a series of pyrrolidin-2-one derivatives connected via two or four methylene units to arylpiperazine fragment. The compounds obtained for α₁- and α₂-adrenoceptors were assessed. The compound with highest affinity for the α₁-adrenoceptors was 1-{4-[4-(2-chloro-phenyl)-piperazin-1-yl]-butyl}-pyrrolidin-2-one (10 h) with pKi=7.30. Compound with pKi (α₁) ⩾6.44 were evaluated in functional bioassays for intrinsic activity at α₁A- and α₁B-adrenoceptors. All compounds tested were antagonists of the α₁B-adrenoceptors. Additionally, compounds 10e and 10h were α₁A-adrenoceptors antagonist. The dual α₁A-/α₁B-adrenoceptors antagonists, compounds 10e and 10h were also tested in vivo for their hypotensive activity in rats. These compounds, when dosed of 1.0 mg/kg iv in normotensive, anesthetized rats, significantly decreased systolic and diastolic pressure and their hypotensive effects lasted for longer than one hour.

Keywords: Hypotensive activity; Long-chain arylpiperazines; Pyrrolidin-2-one derivatives; α-Adrenoceptors antagonists.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adrenergic alpha-1 Receptor Antagonists / chemical synthesis
  • Adrenergic alpha-1 Receptor Antagonists / chemistry*
  • Adrenergic alpha-1 Receptor Antagonists / pharmacology*
  • Animals
  • Dose-Response Relationship, Drug
  • Hypotension / chemically induced*
  • Male
  • Molecular Structure
  • Piperazines / chemical synthesis
  • Piperazines / chemistry
  • Piperazines / pharmacology*
  • Pyrrolidinones / chemistry*
  • Pyrrolidinones / pharmacology*
  • Rats
  • Rats, Wistar
  • Receptors, Adrenergic, alpha-1 / metabolism*
  • Structure-Activity Relationship

Substances

  • Adrenergic alpha-1 Receptor Antagonists
  • Piperazines
  • Pyrrolidinones
  • Receptors, Adrenergic, alpha-1