A novel histamine 2(H2) receptor antagonist with gastroprotective activity. II. Synthesis and pharmacological evaluation of 2-furfuryl-thio and 2-furfurylsulfinyl acetamide derivatives with heteroaromatic rings

Chem Pharm Bull (Tokyo). 1998 Apr;46(4):616-22. doi: 10.1248/cpb.46.616.

Abstract

We recently found that N-[3-[3-(piperidinomethyl)phenoxyl]propyl]acetamide derivatives with a thioether function showed gastric anti-secretory and gastroprotective activities and that the thioether function (particularly furfurylthio or furfurylsulfinyl) was essential for gastroprotection. In the present study, a series of 2-furfurylthio and 2-furfurylsulfinyl acetamide derivatives were synthesized and evaluated for histamine H2 receptor antagonistic activity, gastric anti-secretory activity and gastroprotective action. Based on the structure of N-[3-[3-(piperidinomethyl)phenoxyl]propyl]acetamide, we designed compounds, in which the 3-(piperidinomethyl)phenoxy part is substituted with many types of heteroaromatic ring attached to the tertiary amine and the propyl group is replaced with other carbon linkages. Structure-activity relationships are discussed. 2-Furfurylsulfinyl-N-[4-[4-(piperidinomethyl)-2-pyridylox y]- (Z)-2-butenyl]acetamide was the most potent among the tested compounds and was given the code designation FRG-8813.

MeSH terms

  • Acetamides / chemical synthesis*
  • Acetamides / pharmacology
  • Animals
  • Anti-Ulcer Agents / chemical synthesis*
  • Anti-Ulcer Agents / pharmacology
  • Gastric Acid / metabolism
  • Guinea Pigs
  • Heart Rate / drug effects
  • Histamine / pharmacology
  • Histamine H2 Antagonists / chemical synthesis*
  • Histamine H2 Antagonists / pharmacology
  • Male
  • Piperidines / chemical synthesis*
  • Piperidines / pharmacology
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology
  • Rats
  • Rats, Wistar
  • Stomach / drug effects
  • Structure-Activity Relationship

Substances

  • Acetamides
  • Anti-Ulcer Agents
  • Histamine H2 Antagonists
  • Piperidines
  • Pyridines
  • lafutidine
  • Histamine