Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole

Citation: SHI Xiu-Dong, GE Bing-Chen, XU Jiang-Ping, ZHOU Zhong-Zhen. Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole[J]. Chinese Journal of Structural Chemistry, 2016, 35(1): 34-38. doi: 10.14102/j.cnki.0254-5861.2011-0857 shu

Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole

1.
a Neuropharmacology Group, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China;
2.
b Key Laboratory of New Drug Screening of Guangdong Province, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China
基金项目:
The project was supported by the National Natural Science Foundation of China (No. 21002048) (No. 21002048)

ing Young Teachers in Guangdong Province (No. C1032190) (No. C1032190)

摘要: The title compound 6-chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-ben- zofuro[3,2-c]pyrazole (5, C₂₁H₁₃Cl₂N₃O, M_r = 394.26) was synthesized and characterized by elemental analysis, ¹H NMR,¹³C NMR and X-ray single-crystal diffraction. The structure reveals that the crystal belongs to the triclinic system, space group P1 with a = 7.8829(8), b = 10.3281(10), c = 11.7615(12) Å, α = 83.5552(2), β = 79.921(2), γ = 70.189(2)°, V = 885.54(15) Å³, Z = 2, D_c = 1.479 g/cm³, μ = 0.383 mm^-1, F(000) = 404, R = 0.0538 and wR = 0.1335 for 2453 observed reflections with I > 2σ(I). The result reveals that the crystal structure of the title compound 5 is stabilized by three C-Cl…π interactions and π…π stacking interaction. In addition, the preliminary investigation showed that 5 exhibits remarkably good antitumor activity against the MCF-7 and A549 cell lines.

关键词:

English

Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole

1.
a Neuropharmacology Group, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China;
2.
b Key Laboratory of New Drug Screening of Guangdong Province, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China
Received Date: 17 June 2015
Fund Project:

Abstract: The title compound 6-chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-ben- zofuro[3,2-c]pyrazole (5, C₂₁H₁₃Cl₂N₃O, M_r = 394.26) was synthesized and characterized by elemental analysis, ¹H NMR,¹³C NMR and X-ray single-crystal diffraction. The structure reveals that the crystal belongs to the triclinic system, space group P1 with a = 7.8829(8), b = 10.3281(10), c = 11.7615(12) Å, α = 83.5552(2), β = 79.921(2), γ = 70.189(2)°, V = 885.54(15) Å³, Z = 2, D_c = 1.479 g/cm³, μ = 0.383 mm^-1, F(000) = 404, R = 0.0538 and wR = 0.1335 for 2453 observed reflections with I > 2σ(I). The result reveals that the crystal structure of the title compound 5 is stabilized by three C-Cl…π interactions and π…π stacking interaction. In addition, the preliminary investigation showed that 5 exhibits remarkably good antitumor activity against the MCF-7 and A549 cell lines.

Key words:

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1.
沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole

English

Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole

English

Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

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