Indanylidenes. 2. Design and synthesis of (E)-2-(4-chloro-6-fluoro-1-indanylidene)-N-methylacetamide, a potent antiinflammatory and analgesic agent without centrally acting muscle relaxant activity

J Med Chem. 2003 Jan 30;46(3):409-16. doi: 10.1021/jm020068k.

Abstract

Extension of the structure-activity relationship studies that led to the discovery of the nonsedating potent muscle relaxant, antiinflammatory, and analgesic agent (E)-2-(4,6-difluoro-1-indanylidene)acetamide, 1, has given rise to (E)-2-(4-chloro-6-fluoro-1-indanylidene)-N-methylacetamide, 2. Compound 2 is a potent antiinflammatory and analgesic agent without centrally acting muscle relaxant activity.

MeSH terms

  • Acetamides / chemical synthesis*
  • Acetamides / chemistry
  • Acetamides / pharmacology
  • Analgesics / chemical synthesis*
  • Analgesics / chemistry
  • Analgesics / pharmacology
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Hypnotics and Sedatives / chemical synthesis
  • Hypnotics and Sedatives / chemistry
  • Hypnotics and Sedatives / pharmacology
  • Indans / chemical synthesis*
  • Indans / chemistry
  • Indans / pharmacology
  • Mice
  • Muscle Relaxants, Central / chemical synthesis
  • Muscle Relaxants, Central / chemistry
  • Muscle Relaxants, Central / pharmacology
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 2-(4-chloro-6-fluoro-1-indanylidene)-N-methylacetamide
  • Acetamides
  • Analgesics
  • Anti-Inflammatory Agents, Non-Steroidal
  • Hypnotics and Sedatives
  • Indans
  • Muscle Relaxants, Central