DABCO-catalyzed sp(3) C-H activation: rapid access to isoxazole or coumarin-fused 3-quaternary carbon oxindoles and isoxazole-fused pyrrolidinones

doi:10.1016/j.tetlet.2015.08.059

	DABCO-catalyzed sp(3) C-H activation: rapid access to isoxazole or coumarin-fused 3-quaternary carbon oxindoles and isoxazole-fused pyrrolidinones
	Liu,Xiong-Li; Jing,De-Hong; Yao,Zhen; Zhang,Wen-Hui; Liu,Xiong-Wei; Yang,Zhou-Jie; Zhao,Zhi; Zhou,Ying; Li,Xiao-Nian
	2015-10-07
发表期刊	TETRAHEDRON LETTERS
卷号	56 期号:41 页码:5637-5645
摘要	A facile and efficient methodology was developed for the synthesis of isoxazole or coumarin-fused 3-quaternary carbon oxindoles and isoxazole-fused pyrrolidinones via DABCO-catalyzed sp(3) C-H activation of 5-methyl-isoxazole or 4-methylcoumarin. Furthermore, the biological activity of the isoxazole or coumarin-fused 3-quaternary carbon oxindoles 3 and 5 has been preliminarily demonstrated by in vitro evaluation against human prostate cancer cells PC-3 and human leukemia cells 1(562 by the MIT-based assays using the commercially available standard drug Cisplatin as a positive control. These results suggested that most of the compounds 3 and 5 showed considerable cytotoxicities to these two cell lines 1(562 and PC-3, and a methyl or an ethyl group of acrylates and an oxindole moiety located in the isoxazole-fused 3-quaternary carbon oxindoles 3 are beneficial for the activity. In addition, the activity of all the afforded isoxazole-fused pyrrolidinones 7 were also evaluated against Gram-positive bacteria Staphylococcus aureus (MTCC96) and Gram-negative bacteria Escherichia coli (ATCC25835) using Penicillin as a standard drug for Gram-positive organism or Streptomycin as standard drug for Gram-negative organism. The results demonstrated that most of the compounds 7 had comparable in vitro inhibitory activity against Gram-positive bacteria Staphylococcus aureus (MTCC96) with the positive control Penicillin. The results also indicated that isoxazole-fused pyrrolidinone analogs had significantly better inhibition ability against Gram-positive bacteria Staphylococcus aureus (MTCC96) than against Gram-negative bacteria Escherichia coli (ATCC25835). (C) 2015 Elsevier Ltd. All rights reserved.
关键词	Isoxazole Or Coumarin-fused 3-quaternary Carbon Oxindoles Isoxazole-fused Pyrrolidinones C-h Activation Antibacterial Activity Antitumor Activity
DOI	10.1016/j.tetlet.2015.08.059
收录类别	SCI
语种	英语
WOS记录号	WOS:000361926100036
引用统计	被引频次：27[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/25179
专题	植物化学与西部植物资源持续利用国家重点实验室
推荐引用方式 GB/T 7714	Liu,Xiong-Li,Jing,De-Hong,Yao,Zhen,et al. DABCO-catalyzed sp(3) C-H activation: rapid access to isoxazole or coumarin-fused 3-quaternary carbon oxindoles and isoxazole-fused pyrrolidinones[J]. TETRAHEDRON LETTERS,2015,56(41):5637-5645.
APA	Liu,Xiong-Li.,Jing,De-Hong.,Yao,Zhen.,Zhang,Wen-Hui.,Liu,Xiong-Wei.,...&Li,Xiao-Nian.(2015).DABCO-catalyzed sp(3) C-H activation: rapid access to isoxazole or coumarin-fused 3-quaternary carbon oxindoles and isoxazole-fused pyrrolidinones.TETRAHEDRON LETTERS,56(41),5637-5645.
MLA	Liu,Xiong-Li,et al."DABCO-catalyzed sp(3) C-H activation: rapid access to isoxazole or coumarin-fused 3-quaternary carbon oxindoles and isoxazole-fused pyrrolidinones".TETRAHEDRON LETTERS 56.41(2015):5637-5645.

条目包含的文件		下载所有文件
文件名称/大小	文献类型	版本类型	开放类型	使用许可
1-s2.0-S004040391530（4853KB）	期刊论文	作者接受稿	开放获取	CC BY-NC-SA	浏览下载