Synthesis and spasmolytic activity of 2-substituted-3-(ω-dialkylamino-alkoxyphenyl)acrylonitriles and related compounds

Article abstract of DOI:10.1248/cpb.31.2023

Several analogs of (Z)-2-(1,2-benzisoxazol-3-yl)-3-[2-(2-piperidinoethoxy)phenyl]-acryloni trile, such as (Z)-2-(1,2-benzisothiazol-3-yl)-, (Z)-2-(1H-indol-3-yl)-, (E)-2-(2-thienyl)- and (E)-2-benzoyl-3-(ω-dialkylaminoalkoxyphenyl)acrylonitriles, were synthesized by means of the Knoevenagel condensation. The descyano analog was prepared by means of the Wittig reaction. Triethylammonium formate reduction of 2-(1,2-benzisoxazol-3-yl)-3-(ω-dialkylaminoalkoxyphenyl)acrylonitriles afforded the dihydro analog. The spasmolytic activities of these analogs were examined. Among these compounds, (Z)-2-(1,2-benzisothiazol-3-yl)-3-[2-(2-piperidinoethoxy)phenyl]-acrylonit rile and (Z)-2-(1,2-benzisothiazol-3-yl)-3-[2-(2-morpholinoethoxy)phenyl]acrylon itrile showed potent antispasmodic activities in vitro and in vivo (in mice).

Full text of DOI:10.1248/cpb.31.2023

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