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
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
收藏
页码:111 / 121
页数:11
相关论文
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 [J].
Cao, RH ;
Chen, Q ;
Hou, XR ;
Chen, HS ;
Guan, HJ ;
Ma, Y ;
Peng, WL ;
Xu, AL .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (17) :4613-4623
[3]   Synthesis of xanthoxyline derivatives with antinociceptive and antioedematogenic activities [J].
Cechinel, V ;
Vaz, ZR ;
Zunino, L ;
Calixto, JB ;
Yunes, RA .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1996, 31 (10) :833-839
[4]   Design, synthesis and cytotoxic activities of novel hybrid compounds between dihydrobenzofuran and imidazole [J].
Chen, Wen ;
Yang, Xiao-Dong ;
Li, Yan ;
Yang, Li-Juan ;
Wang, Xue-Quan ;
Zhang, Gao-Lan ;
Zhang, Hong-Bin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (11) :4250-4255
[5]   Imidazole alkaloids from Lepidium meyenii [J].
Cui, BL ;
Zheng, BL ;
He, K ;
Zheng, QY .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (08) :1101-1103
[6]   ORAL HYPOGLYCEMIC AGENTS - DISCOVERY AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF PHENACYLIMIDAZOLIUM HALIDES [J].
DOMINIANNI, SJ ;
YEN, TT .
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 [J].
Fortuna, Cosimo Gianluca ;
Barresi, Vincenza ;
Berellini, Giuliano ;
Musumarra, Giuseppe .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (07) :4150-4159
[8]   Hybrid Compound Design To Overcome the Gatekeeper T338M Mutation in cSrc [J].
Getlik, Matthaeus ;
Gruetter, Christian ;
Simard, Jeffrey R. ;
Klueter, Sabine ;
Rabiller, Matthias ;
Rode, Haridas B. ;
Robubi, Armin ;
Rauh, Daniel .
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 [J].
Hayakawa, I ;
Shioya, R ;
Agatsuma, T ;
Furukawa, H ;
Naruto, S ;
Sugano, Y .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (17) :4383-4387
[10]   Synthesis and biological evaluation of novel A-ring modified hexacyclic camptothecin analogues [J].
Kim, DK ;
Ryu, DH ;
Lee, JY ;
Lee, N ;
Kim, YW ;
Kim, JS ;
Chang, K ;
Im, GJ ;
Kim, TK ;
Choi, WS .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (10) :1594-1602