Synthesis and blocking activities of isoindolinone- and isobenzofuranone-containing phenoxylalkylamines as potent α(1)-adrenoceptor antagonists

Chem Pharm Bull (Tokyo). 2011;59(1):96-9. doi: 10.1248/cpb.59.96.

Abstract

This paper describes the synthesis and blocking activities of twelve new isoindolinone- and isobenzofuranone-containing phenoxylalkylamines as potent α(1)-Adrenoceptor antagonists. These compounds were synthesized in moderate to good yields starting from 3,4-dimethylphenol, and characterized with (1)H-NMR, MS, IR and elemental analysis. Their blocking activities toward α(1)-Adrenoceptors were evaluated on isolated rat anococcygeus muscles. The results indicated that these compounds were very strong in blocking α(1)-Adrenoceptors, and most of them exhibited activities that were comparable to that of known potent α(1)-Adrenoceptor antagonist 1-(2,6-dimethylphenoxy)-2-(3,4-dimethoxyphenylethylamino)propane hydrochloride (DDPH).

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
  • Amines / chemistry*
  • Animals
  • Benzofurans / chemical synthesis
  • Benzofurans / chemistry*
  • Benzofurans / pharmacology
  • Isoindoles / chemical synthesis
  • Isoindoles / chemistry*
  • Isoindoles / pharmacology
  • Muscles / metabolism
  • Phenethylamines / chemistry
  • Phenethylamines / pharmacology
  • Rats
  • Receptors, Adrenergic, alpha / chemistry*
  • Receptors, Adrenergic, alpha / metabolism
  • Structure-Activity Relationship

Substances

  • Adrenergic alpha-1 Receptor Antagonists
  • Amines
  • Benzofurans
  • Isoindoles
  • Phenethylamines
  • Receptors, Adrenergic, alpha
  • 1-(2,6-dimethylphenoxy)-2-(3,4-dimethoxyphenylethylamino)propane