Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts
Liu Zhengfen1; Zhang Chaobo1; Duan Shengzu1; Liu Yang1; Chen Wen1; Li Yan2; Zhang Hongbin1; Yang Xiaodong1
2017-06-01
Source PublicationCHINESE JOURNAL OF ORGANIC CHEMISTRY
ISSN0253-2786
Volume37Issue:6Pages:1506-1515
AbstractA series of novel hybrid compounds between indolo[b]tetrahydrofuran and imidazolium salts were prepared from tryptophol by four steps of Sharpless epoxidation, amidation, coupling and salt formation. Their structures were confirmed by H-1 NMR, C-13 NMR, HRMS and X-ray crystallographic analysis. These compounds were evaluated in vitro against a panel of human tumor cell lines. The results showed that 1-((3aR,8aS)-3,3a-dihydro-3a-hydroxy-2H-furo[2,3-b]indol-8(8aH)-yl)ethanone-3-(2-(naphthalen-2-yl)-2-oxoethyl)-5,6-dimethyl-1H-benzo[d]-imidazol-3-ium bromide (20) and 1-((3aR,8aS)-3,3a-di-hydro-3a-hydroxy-2H-furo[2,3-b]indol-8(8aH)-yl)ethanone-3-(2-naphthylmethyl)-5,6-dimethyl-1H-benzo[d]imidazol-3-ium bromide (22) exhibited higher inhibitory activity selectively against SMMC-7721, MCF-7 and SW480 cell lines compared with DDP. In particular, 1-((3aR,8aS)-3,3a-dihydro-3a-hydroxy-2H-furo[2,3-b]indol-8(8aH)-yl)ethanone-3-(2-bromobenzyl)-5,6-dimethyl-1H-benzo[d]imidazol-3-ium bromide (24) was more selective to SW-480 cell lines with IC50 values 2.0-fold lower than DDP.
KeywordIndolo[b]Tetrahydrofuran Imidazolium Salts Hybrid Compound Cytotoxic Activity
Subject AreaChemistry, Organic
DOI10.6023/cjoc201610043
Indexed BySCI
Language英语
WOS IDWOS:000406824700023
Citation statistics
Cited Times:2[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/54950
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.Yunnan Univ, Key Lab Med Chem Nat Resource, Minist Educ, Kunming 650091, Yunnan, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Yunnan, Peoples R China
Recommended Citation
GB/T 7714
Liu Zhengfen,Zhang Chaobo,Duan Shengzu,et al. Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2017,37(6):1506-1515.
APA Liu Zhengfen.,Zhang Chaobo.,Duan Shengzu.,Liu Yang.,Chen Wen.,...&Yang Xiaodong.(2017).Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts.CHINESE JOURNAL OF ORGANIC CHEMISTRY,37(6),1506-1515.
MLA Liu Zhengfen,et al."Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts".CHINESE JOURNAL OF ORGANIC CHEMISTRY 37.6(2017):1506-1515.
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