Synthesis and SAR of pyridazinone-substituted phenylalanine amide alpha4 integrin antagonists

Bioorg Med Chem Lett. 2008 Feb 15;18(4):1331-5. doi: 10.1016/j.bmcl.2008.01.022. Epub 2008 Jan 11.

Abstract

Structural modification and cellular adhesion inhibition activities of pyridazinone-substituted phenylalanine amide alpha(4) integrin antagonists are described. Functionality requirements for the arylamide moiety and the carboxylic acid group were demonstrated. The study also revealed novel structure-activity relationships (SAR) for arylated pyridazinones. A correlation between bioavailability and permeability was also explored. A selected compound showed effectiveness in a mouse leukocytosis study.

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Amides / pharmacokinetics
  • Amides / pharmacology*
  • Animals
  • Biological Availability
  • Caco-2 Cells
  • Cell Adhesion / drug effects
  • Humans
  • Integrin alpha4 / chemistry
  • Integrin alpha4 / metabolism*
  • Intestinal Absorption
  • Leukocytosis / drug therapy
  • Mice
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemical synthesis
  • Phenylalanine / pharmacokinetics
  • Phenylalanine / pharmacology
  • Pyridazines / chemical synthesis
  • Pyridazines / chemistry*
  • Pyridazines / pharmacokinetics
  • Pyridazines / pharmacology*
  • Rats
  • Structure-Activity Relationship

Substances

  • Amides
  • Pyridazines
  • Integrin alpha4
  • Phenylalanine