Synthesis and spasmolytic activity of 2-substituted-3-(.OMEGA.-dialkylaminoalkoxyphenyl)acrylonitriles and related compounds.

Naruto, Shunsuke; Mizuta, Hiroyuki; Yoshida, T.; Uno, Hitoshi; Kawashima, Katsuyoshi; Kadokawa, Toshiaki; Nishimura, Haruki

doi:10.1248/cpb.31.2023

Cited by 15 publications

(15 citation statements)

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“…For the biological activity, see: Naruto et al (1983); Parmar et al (1988); Shiba (1996); Sanna et al (1999Sanna et al ( , 2000; Ohsumi et al (1998); Saczewski et al (2004). For similar structures, see : Choi et al (2007); Seo et al (2009);Sonar et al (2007).…”

Section: Related Literaturementioning

confidence: 99%

“…Acrylonitrile analogs that incorporate 1,2,4-triazole, benzimidazole, or 1,3,5-triazine heterocyclic groups have been found to possess interesting biological properties such as spasmolytic (Naruto et al, 1983), antioxidative (Parmar et al, 1988), insecticidal (Shiba, 1996), antitubercular (Sanna et al, 1999(Sanna et al, , 2000 and cytotoxic (Ohsumi et al, 1998;Saczewski et al, 2004) activities. From our previous studies, we reported the X-ray crystallographic data of two benzothiophene acrylonitrile analogs (Sonar et al, 2007).…”

Section: S1 Commentmentioning

confidence: 99%

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(Z)-3-(1-Benzofuran-2-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile

2012

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Key indicators: single-crystal X-ray study; T = 90 K; mean (C-C) = 0.004 Å; R factor = 0.064; wR factor = 0.186; data-to-parameter ratio = 16.6.In the title compound, C 20 H 17 NO 4 , the double bond of the acrylonitrile group separating the 1-benzofuran moiety from the 3,4,5-trimethoxyphenyl ring has Z geometry. The 1-benzofuran groups are -stacked with inversion-related counterparts such that the furan ring centroid-centroid distance is 3.804 (5) Å . The dihedral angle between the planes of the trimethoxyphenyl ring and the acrylonitrile group is 24.2 (2) . Related literatureFor the biological activity, see: Naruto et al.

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Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

(Z)-3-(1-Benzofuran-2-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile

2012

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“…For biological activity of similar acrylonitriles, see: Naruto et al (1983); Ohsumi et al (1998); Saczewski et al (2004). For the molecular structures of (E)-3-(benzo[b]thiophen-2-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile and (Z)-3-(benzo[b]thiophen-2-yl)-2-(3,4-dimethoxyphenyl)acrylonitrile, see: Sonar et al (2007).…”

Section: Related Literaturementioning

confidence: 99%

“…A number of 2,3-diarylacrylonitrile analogs have been found to possess interesting biological properties such as spasmolytic (Naruto et al, 1983), and cytotoxic activities (Ohsumi et al, 1998 andSaczewski et al, 2004). Previously, we have reported on the crystallographic data of benzothiophene acrylonitrile analogs (Sonar et al, 2007).…”

Section: S1 Commentmentioning

confidence: 99%

(Z)-3-(1H-Indol-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile

2012

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In the title compound, C20H18N2O3, the C=C bond of the acrylonitrile group that links the indole and the 3,4,5-trimethoxyphenyl rings has Z geometry, with dihedral angles between the plane of the acrylonitrile unit and the planes of the benzene and indole ring systems of 21.96 (5) and 38.94 (7)°, respectively. The acrylonitrile group is planar (r.m.s. deviation from planarity = 0.037 Å). Molecules are linked into head-to-tail chains that propagate along the b-axis direction by bifurcated N—H⋯O intermolecular hydrogen bonds, which form an R 1 2(5) motif between the indole NH group and the two methoxy O atoms furthest from the nitrile group.

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“…Substituted acrylonitriles have been found to possess interesting biological properties which range from spasmolytic [1], antioxidative [2], insecticidal [3], and antitubercular [4,5] to cytotoxic [6,7] activities. Among them, structures with heterocyclic residues such as 1,2,4-triazoles 1, benzimidazoles 2, or 1,3,5-triazines 3 at position 2 of the acrylonitrile system ( Fig.…”

Section: Introductionmentioning

confidence: 99%