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学科主题: 药学
题名:
Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives and studies of the reaction mechanism
作者: Han, Dong2; Meng, Xiang-Bao1,2; Wang, Lin-Na2; Liu, Hong2; Yao, Yun2; Wang, Zhuo1; Yang, Zhen-Jun1; Liu, Zhen-Min1; Li, Zhong-Jun1,2
刊名: TETRAHEDRON-ASYMMETRY
发表日期: 2009-03-11
DOI: 10.1016/j.tetasy.2008.12.033
卷: 20, 期:4, 页:399-410
收录类别: SCI ; IC
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Chemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical
研究领域[WOS]: Chemistry
关键词[WOS]: ACETYLATING CONDITIONS ; NMR ANALYSIS ; 1,3,4-OXADIAZOLES ; HETEROCYCLES ; ACID ; BENZOYLHYDRAZONE ; ELUCIDATION
英文摘要:

A series of novel alkyl Substituted fructose-based oxadiazoles were synthesized and their cytotoxic activities toward tumor cells were investigated. We studied the reaction mechanism and the stereochemistry of the reaction. Tautomerization between isomers 2 and 3 was observed in solution. The tautomerization was accelerated by heating or in the presence of acetic acid. An intermediate 6 during the heterocyclization was isolated, and two different pathways for the heterocyclization were suggested. On the basis of these findings, an efficient method, with the assistance Of Microwave irradiation was developed for the synthesis of 4 and S. The yields were satisfactory and no by-products were found. We also proposed that the (R/S)-configurations of oxadiazoles were determined by the E/Z configurations of hydrazones. (c) 2009 Elsevier Ltd. All rights reserved,

语种: 英语
所属项目编号: 20732001 ; 30672525
项目资助者: National Natural Science Foundation of China
WOS记录号: WOS:000265562600002
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/62922
Appears in Collections:北京大学药学院_化学生物学系_期刊论文

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作者单位: 1.Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, Dept Biol Chem, Beijing 100191, Peoples R China

Recommended Citation:
Han, Dong,Meng, Xiang-Bao,Wang, Lin-Na,et al. Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives and studies of the reaction mechanism[J]. TETRAHEDRON-ASYMMETRY,2009,20(4):399-410.
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