Synthesis, Crystal Structure and Biological Activity of (2,4-Dihydroxy-3,6-ditnethoxyphenyl)-((1R,2S,3S,4R,7R)-7-isopropyl-5-tnethyl-3-phenylbicyclo[2.2.2]-oct-5-en-2-yl)methanone

被引：0

作者：

Sun Zhen-Liang ^{[1
]}

Du Peng ^{[2
]}

Yan Xue-Bing ^{[1
]}

Li Hao ^{[1
]}

Huang Lin-Sheng ^{[1
]}

Qu Xiao ^{[1
]}

Kong Cheng ^{[1
]}

Lv Zhi-Liang ^{[2
]}

Qin Huang-Long ^{[1
]}

机构：

[1] Tongji Univ, Med Coll, Shanghai 200092, Peoples R China

[2] Chinese State Inst Pharmaceut Ind, Zhangjiang Branch Inst, Shanghai 201203, Peoples R China

来源：

CHINESE JOURNAL OF STRUCTURAL CHEMISTRY | 2018年 / 37卷 / 11期

基金：

中国博士后科学基金;

关键词：

monoterpene; total synthesis; crystal structure; biological activity; ANTIFUNGAL ACTIVITY; PURIFICATION;

D O I：

10.14102/j.cnki.0254-5861.2011-1905

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The crystal structure of the natural terpene derivative (2,4-dihydroxy-3,6-dimethoxyphenyl)((1R,2S,3S,4R,7R)-7-isopropyl-5-methyl-3-phenylbicyclo [2.2.2]oct-5-en-2-yl)-methanone was determined by single-crystal X-ray diffraction method. The compound crystallizes in triclinic, space group P2(1)/c with a = 16.1444(9), b = 16.5294(9), c = 19.7875(11) angstrom, V= 5280.4(5) angstrom(3) , Z = 4, D-c = 1.209 g/cm(3), F(000) = 2064, mu(CuK alpha) = 0.675 mm(-1), S = 1.069, R = 0.0520 and wR (I> 2 sigma(I)) = 0.1392. The spiro structure constructed by Diels-Alder reaction was highly symmetric. In addition, the title compound showed inhibitory activities against cancer cell line with varied potencies.

引用

页码：1718 / 1722

页数：5

共 18 条

[1] Purification and properties of growth stage-dependent antiviral proteins from the leaves of Celosia cristata [J].

Balasubrahmanyam, A ;

Baranwal, VK ;

Lodha, ML ;

Varma, A ;

Kapoor, HC .

PLANT SCIENCE, 2000, 154 (01) :13-21

[2] Chemical stability and colorant properties of betaxanthin pigments from Celosia argentea [J].

Cai, YZ ;

Sun, M ;

Schliemann, W ;

Corke, H .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (09) :4429-4435

[3] Natural Terpenes as Penetration Enhancers for Transdermal Drug Delivery [J].

Chen, Jun ;

Jiang, Qiu-Dong ;

Chai, Ya-Ping ;

Zhang, Hui ;

Peng, Pei ;

Yang, Xi-Xiong .

MOLECULES, 2016, 21 (12)

[4] Electron transfer-initiated Diels-Alder cycloadditions of 2′-hydroxychalcones [J].

Cong, Huan ;

Ledbetter, Dustin ;

Rowe, Gerard T. ;

Caradonna, John P. ;

Porco, John A., Jr. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9214-+

[5] Utility and synthetic uses of Mannich reaction: An efficient route for synthesis of thiadiazino-[1,3,5][3,2-a]benzimidazoles [J].

El-Wareth, A ;

Sarhan, AO ;

Abdel-Hafez, SH ;

El-Sherief, H ;

Aboel-Fadl, T .

SYNTHETIC COMMUNICATIONS, 2006, 36 (08) :987-996

[6] The function of terpene natural products in the natural world [J].

Gershenzon, Jonathan ;

Dudareva, Natalia .

NATURE CHEMICAL BIOLOGY, 2007, 3 (07) :408-414

[7]

Li M, 2004, CHINESE J STRUC CHEM, V23, P11

[8] Convenient Synthesis of Wogonin, A Flavonoid Natural Product with Extensive Pharmacological Activity [J].

Li, Zhi-Yu ;

Cao, Xin ;

Wang, Xin ;

Guo, Qing-Long ;

You, Qi-Dong .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2009, 41 (04) :327-330

[9]

National Research Council, 2006, LOST CROPS OF AFRICA, VII, P93

[10]

Shanmugam S., 2011, Journal of Applied Pharmaceutical Science, V1, P94

← 1 2 →