Synthesis, spasmolytic activity and structure-activity relationship studies of a series of thiobenzanilides

Description

The irritable bowel syndrome and other functional bowel disorders are characterized by gastrointestinal hypermotility and abdominal pain. In line of our attempts to identify new compounds with spasmolytic activity we recently presented a series of benzanilides derived from the phytoalexin resveratrol. Most of the compounds tested showed activity in the range of 3 – 30 ľM. Within this work we extended our studies on thiobenzanilides. Interestingly, the exchange of the carbonyl group by a thiocarbonyl group generally increased the spasmolytic effect. Furthermore, structure-activity relationship studies revealed a remarkable difference of trifluoro vs trimethoxy-substituted anilides with the latter being 100fold less active at the terminal ileum of guinea pigs. However, trimethoxyanilides exhibit a remarkable selectivity against aorta. Finally, the exchange of nitro by fluoro does not significantly influence the spasmolytic effect at the terminal ileum. The final lead compound AST31 showed an IC50 value of 0.13 ľM.

Period	2009
Event title	Nicht angegeben
Event type	Other
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