Citation:
ZHONG Yan, LIU Ya-Lin, XU Zhao-Ying, XU Yi, LI Ping, WU Bin. Synthesis, Crystal Structure and Anti-ischemic Activity of (E)-1-(4-(Bis(4-methoxyphenyl)methyl)piperazin-1-yl)-3- (4-acetoxy-3-methoxyphenyl)prop-2-en-1-one[J]. Chinese Journal of Structural Chemistry,
2015, 34(5): 681-687.
doi:
10.14102/j.cnki.0254-5861.2011-0583
Synthesis, Crystal Structure and Anti-ischemic Activity of (E)-1-(4-(Bis(4-methoxyphenyl)methyl)piperazin-1-yl)-3- (4-acetoxy-3-methoxyphenyl)prop-2-en-1-one
摘要:
A new cinnamide derivative, (E)-1-(4-(bis(4-methoxyphenyl)methyl)piperazin- 1-yl)-3-(4-acetoxy-3-methoxyphenyl)prop-2-en-1-one (C31H34N2O6, Mr=530.60), has been synthesized by the condensation of 1-(bis(4-methoxyphenyl)methyl)piperazine and (E)-3-(4- acetoxy-3-methoxyphenyl)acrylic acid. The compound was characterized by 1H NMR, 13C NMR, H RMS and single-crystal X-ray diffraction. The crystal belongs to the orthorhombic system, space group P212121 with a=24.946(5), b=7.6380(15), c=14.555(3) Å, V=2773.3(10) Å3, Z=4, Dc=1.271 g/cm3, F(000)=1128, μ=0.088 mm-1, MoKα radiation (λ=0.71073 Å), the final R=0.0641 and wR=0.1170. A total of 3009 unique reflections were collected, of which 1760 with I>2σ(I) were observed. Intramolecular C(17)-H(17B)···O(3) and C(22)-H(22A)···O(3) interactions as well as intermolecular C(27)-H(27A)···O(3) hydrogen bonds help to stabilize the crystal structure. The title compound was evaluated for the anti-ischemic activity in vitro and in vivo. The bioassay results indicated that the title compound displayed efficient activities against glutamine-induced neurotoxicity in PC12 cells and significantly prolonged the survival time of mice subjected to acute cerebral ischemia.
English
Synthesis, Crystal Structure and Anti-ischemic Activity of (E)-1-(4-(Bis(4-methoxyphenyl)methyl)piperazin-1-yl)-3- (4-acetoxy-3-methoxyphenyl)prop-2-en-1-one
Abstract:
A new cinnamide derivative, (E)-1-(4-(bis(4-methoxyphenyl)methyl)piperazin- 1-yl)-3-(4-acetoxy-3-methoxyphenyl)prop-2-en-1-one (C31H34N2O6, Mr=530.60), has been synthesized by the condensation of 1-(bis(4-methoxyphenyl)methyl)piperazine and (E)-3-(4- acetoxy-3-methoxyphenyl)acrylic acid. The compound was characterized by 1H NMR, 13C NMR, H RMS and single-crystal X-ray diffraction. The crystal belongs to the orthorhombic system, space group P212121 with a=24.946(5), b=7.6380(15), c=14.555(3) Å, V=2773.3(10) Å3, Z=4, Dc=1.271 g/cm3, F(000)=1128, μ=0.088 mm-1, MoKα radiation (λ=0.71073 Å), the final R=0.0641 and wR=0.1170. A total of 3009 unique reflections were collected, of which 1760 with I>2σ(I) were observed. Intramolecular C(17)-H(17B)···O(3) and C(22)-H(22A)···O(3) interactions as well as intermolecular C(27)-H(27A)···O(3) hydrogen bonds help to stabilize the crystal structure. The title compound was evaluated for the anti-ischemic activity in vitro and in vivo. The bioassay results indicated that the title compound displayed efficient activities against glutamine-induced neurotoxicity in PC12 cells and significantly prolonged the survival time of mice subjected to acute cerebral ischemia.
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Key words:
- cinnamide
- / crystal structure
- / synthesis
- / anti-ischemic activity
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