Identification and optimization of novel 2-(4-oxo-2-aryl-quinazolin-3(4H)-yl)acetamide vasopressin V3 (V1b) receptor antagonists

Bioorg Med Chem Lett. 2010 Sep 15;20(18):5394-7. doi: 10.1016/j.bmcl.2010.07.118. Epub 2010 Aug 1.

Abstract

The discovery, synthesis, and preliminary structure-activity relationship (SAR) of a novel class of vasopressin V3 (V1b) receptor antagonists is described. Compound 1, identified by high throughput screening of a diverse, three million-member compound collection, prepared using ECLiPS technology, had good activity in a V3 binding assay (IC50=0.20 microM), but less than desirable physicochemical properties. Optimization of compound 1 yielded potent analogs 19 (IC50=0.31 microM) and 24 (IC50=0.12 microM) with improved drug-like characteristics.

MeSH terms

  • Acetamides / chemical synthesis
  • Acetamides / chemistry*
  • Acetamides / pharmacology*
  • Animals
  • Antidiuretic Hormone Receptor Antagonists*
  • Depressive Disorder / drug therapy
  • Humans
  • Quinazolines / chemical synthesis
  • Quinazolines / chemistry*
  • Quinazolines / pharmacology*
  • Rats
  • Receptors, Vasopressin / metabolism*
  • Structure-Activity Relationship

Substances

  • Acetamides
  • Antidiuretic Hormone Receptor Antagonists
  • Quinazolines
  • Receptors, Vasopressin
  • acetamide