Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts

doi:10.6023/cjoc201610043

CORC > 昆明植物研究所 > 中国科学院昆明植物研究所 > 植物化学与西部植物资源持续利用国家重点实验室

	Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts
	Liu Zhengfen 1; Zhang Chaobo 1; Duan Shengzu 1; Liu Yang 1; Chen Wen 1; Li Yan2 ; Zhang Hongbin 1; Yang Xiaodong 1
刊名	CHINESE JOURNAL OF ORGANIC CHEMISTRY
	2017-06-01
卷号	37 期号:6 页码:1506-1515
关键词	Indolo[b]Tetrahydrofuran Imidazolium Salts Hybrid Compound Cytotoxic Activity
ISSN号	0253-2786
DOI	10.6023/cjoc201610043
英文摘要	A 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.
学科主题	Chemistry, Organic
语种	英语
WOS记录号	WOS:000406824700023
内容类型	期刊论文
源URL	[http://ir.kib.ac.cn/handle/151853/54950]
专题	昆明植物研究所_植物化学与西部植物资源持续利用国家重点实验室
作者单位	1.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
推荐引用方式 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.