Synthesis and antitumor activity of novel 2-substituted indoline imidazolium salt derivatives

被引：35

作者：

Xu, Xiao-Liang ^{[1
]}

Yu, Chun-Lei ^{[2
]}

Chen, Wen ^{[1
]}

Li, Ying-Chao ^{[1
]}

Yang, Li-Juan ^{[3
,4
]}

Li, Yan ^{[2
]}

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

[3] Yunnan Minzu Univ, State Ethn Affairs Commiss, Key Lab Ethn Med Resource Chem, Kunming 650500, Peoples R China

[4] Yunnan Minzu Univ, Minist Educ, Kunming 650500, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 05期

关键词：

CYTOTOXIC ACTIVITIES; HYBRID COMPOUNDS; DESIGN; CHECKPOINT; AGENTS; TRANS;

D O I：

10.1039/c4ob02385d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of novel 2-substituted indoline imidazolium salt derivatives has been prepared and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the existence of a substituted benzimidazole ring and substitution of the imidazolyl-3-position with a naphthylacyl or 2-naphthylmethyl group were vital for modulating the cytotoxic activity. Compound 25 was found to be the most potent derivative with IC50 values of 0.24-1.18 mu M, and exhibited cytotoxic activity selectively against MCF-7, SW480, SMMC-7721 and HL-60 cell lines, while compound 26 showed powerful inhibitory activities selectively against SMMC-7721 and A549 cell lines. Compound 25 can induce G2/M phase cell cycle arrest and apoptosis in SMMC-7721 cells.

引用

页码：1550 / 1557

页数：8

共 28 条

[1] Schiff bases of indoline-2,3-dione (isatin) derivatives and nalidixic acid carbohydrazide, synthesis, antitubercular activity and pharmacophoric model building
Aboul-Fadl, Tarek
Bin-Jubair, Fayzah A. S.
Aboul-Wafa, Omima
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (10) : 4578 - 4586
[2] Imidazolium ionic liquids containing selenium: synthesis and antimicrobial activity
Alberto, Eduardo E.
Rossato, Luana L.
Alves, Sydney Hartz
Alves, Diego
Braga, Antonio L.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (04) : 1001 - 1003
[3] Design, synthesis and in vitro antitumor activity of new trans 2-[2-(heteroaryl)vinyl]-1,3-dimethylimidazolium iodides
Ballistreri, FP
Barresi, V
Benedetti, P
Caltabiano, G
Fortuna, CG
Longo, ML
Musumarra, G
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (07) : 1689 - 1695
[4] 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
[5] Synthesis and cytotoxic activities of novel hybrid 2-phenyl-3-alkylbenzofuran and imidazole/triazole compounds
Chen, Wen
Deng, Xiao-Yan
Li, Yan
Yang, Li-Juan
Wan, Wei-Chao
Wang, Xue-Quan
Zhang, Hong-Bin
Yang, Xiao-Dong
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (15) : 4297 - 4302
[6] 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
[7] Imidazole alkaloids from Lepidium meyenii
Cui, BL
Zheng, BL
He, K
Zheng, QY
[J]. JOURNAL OF NATURAL PRODUCTS, 2003, 66 (08): : 1101 - 1103
[8] Design, Synthesis, and Antiviral Evaluation of Purine-β-lactam and Purine-aminopropanol Hybrids
D'hooghe, Matthias
Mollet, Karen
De Vreese, Rob
Jonckers, Tim H. M.
Dams, Gery
De Kimpe, Norbert
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (11) : 5637 - 5641
[9] 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
[10] Fattorusso E., 2008, Modern Alkaloids, DOI DOI 10.1021/ol049317k

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