Chemical and Pharmaceutical Bulletin p. 616 - 622 (1998)
Update date:2022-08-31
Topics:
Hirakawa, Nobuhiko
Matsumoto, Hajime
Hosoda, Akihiko
Sekine, Akihiro
Yamaura, Tetsuaki
Sekine, Yasuo
We recently found that N-[3-[3- (piperidinomethyl)phenoxy]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)phenoxy]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-pyridyloxy]-(Z)- 2-butenyl]acetamide was the most potent among the tested compounds and was given the code designation FRG-8813.
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