Synthesis,Crystal Structure and Antiproliferative Activity of Ethyl 1-(Phenylcarbamoyl)-2-3,4,5-trimethoxyphenyl)cyclopropanecarboxylae

被引:0
作者
张敬一 [1 ]
钟涵宇 [2 ]
史国兵 [1 ]
机构
[1] Department of Pharmacy, General Hospital of Shenyang Military Command
[2] Department of Pharmacy, First Affiliated Hospital,China Medical University
关键词
3; 4; 5-trimethoxyphenyl; synthesis; crystal structure; antiproliferative activities;
D O I
10.14102/j.cnki.0254-5861.2014.06.012
中图分类号
TQ463 [有机化合物药物的生产]; O741.6 [];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ; 1007 ;
摘要
Many small-molecule compounds have been evaluated with potential antiproliferative activities. Ethyl 1-(phenylcarbamoyl)-2-(3,4,5-trimethoxyphenyl)cyclopropanecarboxylate, one novel cyclopropylamide analogue of combretastatin-A4(CA-4), has been synthesized and its crystal structure was characterized by X-ray single-crystal diffraction. The crystal belongs to monoclinic, space group P21/n, with a = 15.0263(3), b = 7.6574(2), c = 19.4117(4), β = 111.9010(10)o, V = 2072.36(8)3, Z = 4, C22H24NO6, Mr = 398.42, Dc = 1.277 Mg/cm3, F(000) = 844, λ(MoKα) = 1.54178 , μ = 0.770 mm–1, R = 0.0546 and wR = 0.1889 for 3319 observed reflections(I > 2σ(I)). Meanwhile, the compound revealed potential antiproliferative activities in several cancer cells in vitro.
引用
收藏
页码:876 / 880
页数:5
相关论文
共 6 条
[1]  
Synthesis and anti-tumor activity of novel ethyl 3-aryl-4-oxo-3,3 a ,4,6-tetrahydro-1 H -furo[3,4- c]pyran-3 a -carboxylates[J] . Tiantian Wang,Jia Liu,Hanyu Zhong,Huan Chen,Zhiliang Lv,Yikai Zhang,Mingfeng Zhang,Dongping Geng,Chunjuan Niu,Yongmei Li,Ke Li.Bioorganic & Medicinal Chemistry Letters . 2011 (11)
[2]  
Efficient and mild synthesis of highly substituted 2,5-dihydrofuran and furan derivatives via stepwise reaction[J] . Tiantian Wang,Jia Liu,Zhiliang Lv,Hanyu Zhong,Huan Chen,Chunjuan Niu,Ke Li.Tetrahedron . 2011 (19)
[3]  
Synthesis and anticonvulsant activity of new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones[J] . Xianran He,Guanpeng Qiu,Jin Yang,Yuling Xiao,Zhongyuan Wu,Guofu Qiu,Xianming Hu.European Journal of Medicinal Chemistry . 2010 (9)
[4]  
Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity[J] . Sylvie Ducki,David Rennison,Meiko Woo,Alexander Kendall,Jérémie Fournier Dit Chabert,Alan T. McGown,Nicholas J. Lawrence.Bioorganic & Medicinal Chemistry . 2009 (22)
[5]  
Synthesis and biological evaluation of cis -locked vinylogous combretastatin-A4 analogues: Derivatives with a cyclopropyl-vinyl or a cyclopropyl-amide bridge[J] . Nancy Ty,Julia Kaffy,Alban Arrault,Sylviane Thoret,Renée Pontikis,Joelle Dubois,Luc Morin-Allory,Jean-Claude Florent.Bioorganic & Medicinal Chemistry Letters . 2009 (5)
[6]   Synthesis and antitumor activity of benzils related to combretastatin A-4 [J].
Mousset, Celiine ;
Giraud, Anne ;
Provot, Olivier ;
Hamze, Abdallah ;
Bignon, Jeromr ;
Liu, Jian-Miao ;
Thoret, Sylviane ;
Dubois, Joelle ;
Brion, Jean-Daniel ;
Alami, Mouad .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (11) :3266-3271