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
| Autor: | Matsumoto Hajime, Akihiko Hosoda, Hirakawa Nobuhiko, Yasuo Sekine, Tetsuaki Yamaura, Akihiro Sekine |
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| Rok vydání: | 1998 |
| Předmět: |
Male
Tertiary amine Stereochemistry medicine.drug_class Pyridines Guinea Pigs Thio Carboxamide Ether Chemical synthesis Gastric Acid chemistry.chemical_compound Structure-Activity Relationship Thioether Piperidines Heart Rate Drug Discovery Acetamides medicine Animals Rats Wistar Stomach Sulfoxide General Chemistry General Medicine Anti-Ulcer Agents Rats chemistry Histamine H2 Antagonists Acetamide Histamine |
| Zdroj: | Chemicalpharmaceutical bulletin. 46(4) |
| ISSN: | 0009-2363 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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