Design, synthesis and biological evaluation of novel hybrid compounds of imidazole scaffold-based 2-benzylbenzofuran as potent anticancer agents

被引：78

作者：

Wang, Xue-Quan ^{[1
]}

Liu, Lan-Xiang ^{[1
]}

Li, Yan ^{[2
]}

Sun, Cheng-Jun ^{[1
]}

Chen, Wen ^{[1
]}

Li, Liang ^{[1
]}

Zhang, Hong-Bin ^{[1
]}

Yang, Xiao-Dong ^{[1
]}

机构：

[1] Yunnan Univ, Sch Chem Sci & Technol, Minist Educ, Key Lab Med Chem Nat Resource, Kunming 650091, Peoples R China

[2] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Peoples R China

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 62卷

基金：

中国国家自然科学基金;

关键词：

Hybrid compound; 2-Benzylbenzofuran; Imidazole; Cytotoxic activities; Structure-activity relationships; CYTOTOXIC ACTIVITIES; DERIVATIVES; ANALOGS; DISCOVERY; SALTS;

D O I：

10.1016/j.ejmech.2012.12.040

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of novel hybrid compounds between 2-benzylbenzofuran and imidazole has been prepared and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the existence of benzimidazole ring and substitution of the imidazolyl-3-positionwith a naphthylacyl or 4-methoxyphenacyl group were vital for modulating cytotoxic activity In particular, hybrid compounds 46 and 47 were found to be the most potent derivatives against 5 strains human tumor cell lines and more active than cisplatin (DDP), and exhibited cytotoxic activities selectively against breast carcinoma (MCF-7) and myeloid liver carcinoma (SMMC-7721), respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

引用

页码：111 / 121

页数：11

共 26 条

[1] Bissantz C., 2009, Patent, Patent No. [US2009/312317 A1, 2009312317]
[2] Synthesis, acute toxicities, and antitumor effects of novel 9-substituted β-carboline derivatives
Cao, RH
Chen, Q
Hou, XR
Chen, HS
Guan, HJ
Ma, Y
Peng, WL
Xu, AL
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (17) : 4613 - 4623
[3] Synthesis of xanthoxyline derivatives with antinociceptive and antioedematogenic activities
Cechinel, V
Vaz, ZR
Zunino, L
Calixto, JB
Yunes, RA
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1996, 31 (10) : 833 - 839
[4] Design, synthesis and cytotoxic activities of novel hybrid compounds between dihydrobenzofuran and imidazole
Chen, Wen
Yang, Xiao-Dong
Li, Yan
Yang, Li-Juan
Wang, Xue-Quan
Zhang, Gao-Lan
Zhang, Hong-Bin
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (11) : 4250 - 4255
[5] Imidazole alkaloids from Lepidium meyenii
Cui, BL
Zheng, BL
He, K
Zheng, QY
[J]. JOURNAL OF NATURAL PRODUCTS, 2003, 66 (08): : 1101 - 1103
[6] ORAL HYPOGLYCEMIC AGENTS - DISCOVERY AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF PHENACYLIMIDAZOLIUM HALIDES
DOMINIANNI, SJ
YEN, TT
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) : 2301 - 2306
[7] Design and synthesis of trans 2-(furan-2-yl)vinyl heteroaromatic iodides with antitumour activity
Fortuna, Cosimo Gianluca
Barresi, Vincenza
Berellini, Giuliano
Musumarra, Giuseppe
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (07) : 4150 - 4159
[8] Hybrid Compound Design To Overcome the Gatekeeper T338M Mutation in cSrc
Getlik, Matthaeus
Gruetter, Christian
Simard, Jeffrey R.
Klueter, Sabine
Rabiller, Matthias
Rode, Haridas B.
Robubi, Armin
Rauh, Daniel
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (13) : 3915 - 3926
[9] A library synthesis of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as anti-tumor agents
Hayakawa, I
Shioya, R
Agatsuma, T
Furukawa, H
Naruto, S
Sugano, Y
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (17) : 4383 - 4387
[10] Synthesis and biological evaluation of novel A-ring modified hexacyclic camptothecin analogues
Kim, DK
Ryu, DH
Lee, JY
Lee, N
Kim, YW
Kim, JS
Chang, K
Im, GJ
Kim, TK
Choi, WS
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (10) : 1594 - 1602

← 1 2 3 →