Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor

Bioorg Med Chem Lett. 2008 Mar 15;18(6):1926-30. doi: 10.1016/j.bmcl.2008.01.127. Epub 2008 Feb 7.

Abstract

A series of novel acylsulfonamide, acylsulfamide, and sulfonylurea bioisosteres of carboxylic acids were prepared as CXCR2 antagonists. Structure-activity relationships are reported for these series. One potent orally bioavailable inhibitor had excellent PK properties and was active in a lung injury model in hyperoxia-exposed newborn rats.

MeSH terms

  • Administration, Oral
  • Animals
  • Animals, Newborn
  • Biological Availability
  • Bronchoalveolar Lavage
  • Carboxylic Acids / chemistry*
  • Carboxylic Acids / pharmacokinetics
  • Carboxylic Acids / pharmacology*
  • Chemotaxis / drug effects
  • Cytochrome P-450 Enzyme System / metabolism
  • Humans
  • Hyperoxia
  • Lung / drug effects*
  • Lung / metabolism
  • Lung Injury
  • Molecular Structure
  • Neutrophils / metabolism
  • Rabbits
  • Rats
  • Receptors, Interleukin-8B / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Sulfonamides / chemistry*
  • Sulfonic Acids / chemistry*
  • Sulfonylurea Compounds / chemistry*

Substances

  • Carboxylic Acids
  • Receptors, Interleukin-8B
  • Sulfonamides
  • Sulfonic Acids
  • Sulfonylurea Compounds
  • Cytochrome P-450 Enzyme System
  • sulfamic acid