Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate

Citation: CHEN Chao-Yue, HE Qin-Ting, SUN Da-Dong, HU Jin-Song. Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate[J]. Chinese Journal of Structural Chemistry, 2016, 35(2): 199-204. doi: 10.14102/j.cnki.0254-5861.2011-0931 shu

Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate

1.
a School of Chemistry and Environmental Engineering, Jiangsu University of Technology, Changzhou, Jiangsu 213001, China;
2.
b School of Chemical Engineering, Anhui University of Science and Technology, Huainan, Anhui 232001, China
基金项目:

Universities of Anhui Province (KJ2014A062) (KJ2014A062)

摘要: Ethyl 3,9-dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate (C₂₃H₂₂O₆, M_r = 394.42) has been synthesized and its structure was determined by ¹H and ¹³C NMR, ESI-MS, elemental analysis, and X-ray single-crystal diffraction. The crystal belongs to the triclinic system, space group P1, with a = 8.8220(17), b = 9.881(2), c = 12.157(2) Å, α = 90.488(3), β = 102.664(4), γ = 98.799(3)°, V = 1020.8(3) Å³, Z = 2, D_c = 1.342 g/cm³, μ = 0.099 mm^-1, F(000) = 436, R = 0.0615 and wR = 0.2501 for 2592 observed reflections with (I > 2σ(I)). In the crystal structure, the coumarin ring system is planar and the 3:4 fused cyclohexane ring adopts distorted half-chair conformation. Rich hydrogen bonding interactions are formed between compound 2 and lattice water molecules. These interactions assemble molecules of 2 into 2D layered networks in an AB stacking sequence. Its in vitro antiproliferative activities against three human cancer cell lines were evaluated by MTT assay.

关键词:

English

Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate

1.
a School of Chemistry and Environmental Engineering, Jiangsu University of Technology, Changzhou, Jiangsu 213001, China;
2.
b School of Chemical Engineering, Anhui University of Science and Technology, Huainan, Anhui 232001, China
Received Date: 06 August 2015

Abstract: Ethyl 3,9-dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate (C₂₃H₂₂O₆, M_r = 394.42) has been synthesized and its structure was determined by ¹H and ¹³C NMR, ESI-MS, elemental analysis, and X-ray single-crystal diffraction. The crystal belongs to the triclinic system, space group P1, with a = 8.8220(17), b = 9.881(2), c = 12.157(2) Å, α = 90.488(3), β = 102.664(4), γ = 98.799(3)°, V = 1020.8(3) Å³, Z = 2, D_c = 1.342 g/cm³, μ = 0.099 mm^-1, F(000) = 436, R = 0.0615 and wR = 0.2501 for 2592 observed reflections with (I > 2σ(I)). In the crystal structure, the coumarin ring system is planar and the 3:4 fused cyclohexane ring adopts distorted half-chair conformation. Rich hydrogen bonding interactions are formed between compound 2 and lattice water molecules. These interactions assemble molecules of 2 into 2D layered networks in an AB stacking sequence. Its in vitro antiproliferative activities against three human cancer cell lines were evaluated by MTT assay.

Key words:

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1.
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Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate

English

Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate

English

Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate

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

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