N-(5-substituted) thiophene-2-alkylsulfonamides as potent inhibitors of 5-lipoxygenase

Bioorg Med Chem. 1997 Apr;5(4):779-86. doi: 10.1016/s0968-0896(97)00025-4.

Abstract

Compound 4k N-[5-(4-fluoro)phenoxythien-2-yl]methanesulfonamide is representative of a new class of potent inhibitors of 5-lipoxygenase (5-LO). These versatile compounds exhibit dose-dependent inhibition of 5-LO with IC50s ranging from 20-100 nM in the rat basophilic leukemia (RBL-1) cell homogenate assay and submicromolar IC50s in both the RBL-1 and human peripheral blood leukocyte (PBL) whole cell assays. Compound 4k also showed significant anti-inflammatory activity in the adjuvant arthritic rat at an oral dose of 3 mg/kg.

MeSH terms

  • Administration, Oral
  • Alkylation
  • Animals
  • Anti-Inflammatory Agents / administration & dosage
  • Anti-Inflammatory Agents / pharmacology
  • Anti-Inflammatory Agents / therapeutic use
  • Arthritis, Experimental / drug therapy
  • Disease Models, Animal
  • Dose-Response Relationship, Drug
  • Ethers / chemical synthesis
  • Humans
  • Leukemia, Basophilic, Acute / enzymology
  • Leukemia, Basophilic, Acute / pathology
  • Leukocytes, Mononuclear / cytology
  • Leukocytes, Mononuclear / drug effects
  • Lipoxygenase Inhibitors / chemical synthesis*
  • Lipoxygenase Inhibitors / chemistry
  • Lipoxygenase Inhibitors / pharmacology
  • Lipoxygenase Inhibitors / therapeutic use
  • Male
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • Sulfides / chemical synthesis
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacology
  • Sulfonamides / therapeutic use
  • Thiophenes / chemistry
  • Tumor Cells, Cultured

Substances

  • Anti-Inflammatory Agents
  • Ethers
  • Lipoxygenase Inhibitors
  • Sulfides
  • Sulfonamides
  • Thiophenes