Novel nitric oxide-releasing isochroman-4-one derivatives: Synthesis and evaluation of antihypertensive activity

Bioorg Med Chem. 2012 Dec 1;20(23):6848-55. doi: 10.1016/j.bmc.2012.09.043. Epub 2012 Sep 28.

Abstract

By coupling nitric oxide (NO)-donor moieties with a natural antihypertensive product (±)-7,8-dihydroxy-3-methyl-isochroman-4-one [(±)-XJP] and its analogue (±)-XJP-B, a series of novel NO-releasing isochroman-4-one derivatives were designed and synthesized. The NO-releasing assay indicated that compounds Ia, Id, IIIb and IIIe released the maximum amount of NO. The maximum reductions of blood pressure of Ia, IIIb and IIIe in SHRs were nearly 40%, which was obviously superior to that of the lead compounds and comparable to that of reference drug captopril. These results suggested that NO-donor/natural product hybrids may provide a promising approach for the discovery of novel antihypertensive agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antihypertensive Agents / chemical synthesis
  • Antihypertensive Agents / chemistry*
  • Antihypertensive Agents / therapeutic use*
  • Blood Pressure / drug effects
  • Chromones / chemical synthesis
  • Chromones / chemistry*
  • Chromones / therapeutic use*
  • Humans
  • Hypertension / drug therapy
  • Male
  • Nitric Oxide / administration & dosage*
  • Nitric Oxide / therapeutic use
  • Nitric Oxide Donors / chemical synthesis
  • Nitric Oxide Donors / chemistry*
  • Nitric Oxide Donors / therapeutic use*
  • Rats
  • Rats, Inbred SHR

Substances

  • Antihypertensive Agents
  • Chromones
  • Nitric Oxide Donors
  • Nitric Oxide