Synthesis and blocking activities of a new class of α₁-adrenoceptor antagonists

Chem Biol Drug Des. 2010 Dec;76(6):505-10. doi: 10.1111/j.1747-0285.2010.01040.x. Epub 2010 Oct 13.

Abstract

Finding effective chemotherapeutic agents for clinical use is a long-lasting goal in medicinal chemistry. In this study, we report a new class of α₁-adrenoceptor (α₁-AR) antagonists. Specifically, we describe the synthesis and the blocking activities toward α₁-AR of 7-(2-hydroxypropoxy)-3,4-dihydroisoquinolin-1(2H)-one 1 and its structurally perturbed analogs 2-11 that were designed according to the principle of bioisosterism. Their structures were identified with IR, (1) H NMR, MS, HRMS and elemental analysis. The blocking activities of compounds 1-11 were evaluated on isolated rat anococcygeus muscles. The results indicated that these compounds showed moderate to good activities. Among them, compound 1 exhibited the highest activity that was comparable to those of known α₁-AR antagonists tamsulosin and DDPH (1-(2,6-dimethylphenoxy)-2-(3,4-di- methoxyphenylethylamino)propane hydrochloride) and thus may be exploitable as a lead compound for the discovery of promising α₁-AR 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
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Isoquinolines / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Muscle Contraction / drug effects*
  • Rats

Substances

  • 7-(2-hydroxypropoxy)-3,4-dihydroisoquinolin-1(2H)-one
  • Adrenergic alpha-1 Receptor Antagonists
  • Isoquinolines