Chemical and Pharmaceutical Bulletin p. 2023 - 2032 (1983)
Update date:2022-09-26
Topics:
Naruto
Mizuta
Yoshida
Uno
Kawashima
Kadokawa
Nishimura
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).
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Doi:10.1007/BF00506875
(1983)Doi:10.1021/jacs.8b12075
(2018)Doi:10.1021/om0509948
(2006)Doi:10.1002/asia.201501143
(2016)Doi:10.1021/ja00869a045
(1962)Doi:10.1007/s11243-010-9412-8
(2010)
