Synthesis and spasmolytic activities of 2-(1,2-benzisoxazol-3-yl)-3-[[omega-(dialkylamino)alkoxy]phenyl]acrylonitriles.
Several 2-(1,2-benzisoxazol-3-yl)-3-[[omega-(dialkylamino)alkoxy]phenyl]acrylonitrile derivatives were synthesized and screened for potential spasmolytic activity. The effect of structural variation of these molecules on biological activities was systematically examined. Among these compounds, (Z)-2-(1,2-benzisoxazol-3-yl)-3-[2-(2-piperidinoethoxy)-phenyl]acrylonitrile (1d), (Z)-2-(1,2-benzisoxazol-3-yl)-3-[2-(2-morpholinoethoxy)phenyl]acrylonitrile (1f), and their analogues (3c,d) having a methoxy substituent at C5 of the benzoisoxazole ring showed potent antispasmodic activities in the in vitro and in vivo studies.
D000181:Acrylonitrile / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002606:Charcoal; D055598:Chemical Phenomena; D002621:Chemistry; D004558:Electric Stimulation; D006168:Guinea Pigs; D007082:Ileum / Q000378:metabolism; D066298:In Vitro Techniques; D007928:Lethal Dose 50; D009130:Muscle, Smooth / Q000187:drug effects; D009570:Nitriles / Q000138:chemical synthesis*; D010276:Parasympatholytics / Q000138:chemical synthesis*
D009570:Nitriles; D010276:Parasympatholytics; D002606:Charcoal; D000181:Acrylonitrile