Microwave-assisted synthesis and biological evaluation of 3,4-diaryl maleic anhydride/N-substituted maleimide derivatives as combretastatin A-4 analogues

被引：33

作者：

Guan, Qi ^{[1
]}

Zuo, Daiying ^{[2
]}

Jiang, Nan ^{[1
]}

Qi, Huan ^{[2
]}

Zhai, Yanpeng ^{[1
]}

Bai, Zhaoshi ^{[2
]}

Feng, Dongjie ^{[1
]}

Yang, Lei ^{[1
]}

Jiang, Mingyang ^{[1
]}

Bao, Kai ^{[1
,3
,4
]}

Li, Chang ^{[1
]}

Wu, Yingliang ^{[2
]}

Zhang, Weige ^{[1
]}

机构：

[1] Shenyang Pharmaceut Univ, Minist Educ, Key Lab Struct Based Drug Design & Discovery, Shenyang 110016, Peoples R China

[2] Shenyang Pharmaceut Univ, Dept Pharmacol, Shenyang 110016, Peoples R China

[3] Beth Israel Deaconess Med Ctr, Dept Med, Div Hematol Oncol, Boston, MA 02215 USA

[4] Harvard Univ, Sch Med, Boston, MA 02215 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2015年 / 25卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Combretastatin A-4; Anti-proliferative activity; Tubulin; Maleic anhydride; N-Substituted maleimide; HETEROFUSED IMIDES; NATURAL-PRODUCTS; TUBULIN; AGENTS; BINDING; COLCHICINE; DESIGN;

D O I：

10.1016/j.bmcl.2014.12.004

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of new CA-4 analogues bearing maleic anhydride/N-substituted maleimide moiety were synthesized via a microwave-assisted process. They were evaluated for the anti-proliferative activities against three tumor cell lines (SGC-7901, HT-1080 and KB). Most compounds showed moderate potencies in micromolar range, with the most promising analogue 6f showing active at submicromolar concentration against HT-1080 cancer cells which was selected to investigate the antitumor mechanisms. In addition, molecular docking studies within the colchicine binding site of tubulin were also in good agreement with the tubulin polymerization inhibitory data and provided a basis for further structure-guided design of novel CA-4 analogues. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：631 / 634

页数：4

共 21 条

[1] Combretastatin a-4 analogs as anticancer agents
Chaudhary, Anurag
Pandeya, S. N.
Kumar, P.
Sharma, Py.
Gupta, S.
Soni, N.
Verma, K. K.
Bhardwaj, G.
[J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (12) : 1186 - 1205
[2] Natural products with maleic anhydride structure: Nonadrides, tautomycin, chaetomellic anhydride, and other compounds
Chen, Xiaolong
Zheng, Yuguo
Shen, Yinchu
[J]. CHEMICAL REVIEWS, 2007, 107 (05) : 1777 - 1830
[3] Tubulin and microtubule structure
Downing, KH
Nogales, E
[J]. CURRENT OPINION IN CELL BIOLOGY, 1998, 10 (01) : 16 - 22
[4] Microtubule-binding agents: a dynamic field of cancer therapeutics
Dumontet, Charles
Jordan, Mary Ann
[J]. NATURE REVIEWS DRUG DISCOVERY, 2010, 9 (10) : 790 - 803
[5] Antiproliferative effects on human tumor cells and rat aortic smooth muscular cells of 2,3-heteroarylmaleimides and heterofused imides
Ferri, Nicola
Beccalli, Egle Maria
Contini, Alessandro
Corsini, Alberto
Antonino, Manuela
Radice, Tiziano
Pratesi, Graziella
Tinelli, Stella
Zunino, Franco
Gelmi, Maria Luisa
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (04) : 1691 - 1701
[6] Synthesis, structural, and biological evaluation of bis-heteroarylmaleimides and bis-heterofused imides
Ferri, Nicola
Radice, Tiziano
Antonino, Manuela
Beccalli, Egle Maria
Tinelli, Stella
Zunino, Franco
Corsini, Alberto
Pratesi, Graziella
Ragg, Enzio M.
Gelmi, Maria Luisa
Contini, Alessandro
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (18) : 5291 - 5299
[7] JORDAN MA, 2004, NAT REV, V4, P947
[8] Design, Synthesis, and Biological Evaluations of 2,5-Diaryl-2,3-dihydro-1,3,4-oxadiazoline Analogs of Combretastatin-A4
Lee, Lauren
Robb, Lyda M.
Lee, Megan
Davis, Ryan
Mackay, Hilary
Chavda, Sameer
Babu, Balaji
O'Brien, Erin L.
Risinger, April L.
Mooberry, Susan L.
Lee, Moses
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (01) : 325 - 334
[9] ANTIMITOTIC NATURAL-PRODUCTS COMBRETASTATIN-A-4 AND COMBRETASTATIN-A-2 - STUDIES ON THE MECHANISM OF THEIR INHIBITION OF THE BINDING OF COLCHICINE TO TUBULIN
LIN, CM
HO, HH
PETTIT, GR
HAMEL, E
[J]. BIOCHEMISTRY, 1989, 28 (17) : 6984 - 6991
[10] Total synthesis of ailanthoidol and precursor XH14 by Stille coupling
Lin, SY
Chen, CL
Lee, YJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) : 2968 - 2971

← 1 2 3 →