Investigation on the oxidation of aryl oxiranylmethanols and the synthesis of 2-aryl-N-thiazolyl-oxirane-2-carboxamides as gincokinase activators
文献类型：期刊论文
| 作者 | Ye, Na1; Xu, Xiangtao2; Li, Fuying1; Ning, Mengmeng3 ; Liu, Zhiqing1; Cao, Yuqing2; Leng, Ying3; Zhang, Ao1
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| 刊名 | TETRAHEDRON LETTERS
 |
| 出版日期 | 2012-08-29 |
| 卷号 | 53期号:35页码:4738-4742 |
| ISSN号 | 0040-4039 |
| 关键词 | Arylacetamides Glucokinase activators Ruthenium-catalyzed Oxo-rearrangement |
| DOI | 10.1016/j.tetlet.2012.06.111 |
| 文献子类 | Article |
| 英文摘要 | RuCl3/NaIO4-initiated oxidation of oxiranemethanols was investigated, and two products, oxirane-2-carboxylic acid and (5'-oxotetrahydrofuran-3-yl)acetic acid, were obtained in variant ratios. The product structures were determined and a tentative mechanism involving oxidation-rearrangement-oxidation process was proposed. Glucokinase enzymatic assay revealed that oxiranecarboxamides 4a-c retained moderate GK activation potency with amide 4a showing an EC50 value of 584 nM and a high activation fold of 3.14. However, (5'-oxotetrahydrofuran-3-yl)acetamide ha is inactive. This study not only provided an alternative protocol to access (5'-oxotetrahydrofuran-3-yl)acetic acid analogs, but also yielded nanomolar GA activators (esp. 4a) for further structure-activity relationship study. (C) 2012 Elsevier Ltd. All rights reserved. |
| WOS关键词 | GLUCOKINASE ACTIVATORS ; THIAZOL-2-YL)-2-ARYL-3-(TETRAHYDRO-2H-PYRAN-4-YL) PROPANAMIDES ; DIABETES THERAPY ; PSN-GK1 |
| 资助项目 | Chinese National Science Foundation[30772625] ; Chinese National Science Foundation[81072528] ; Shanghai Commission of Science and Technology[10410702600] ; Shanghai Commission of Science and Technology[10JC1417100] ; Shanghai Commission of Science and Technology[10dz1910104] ; National Science & Technology Major Project on 'Key New Drug Creation and Manufacturing Program'[2009ZX09301-001] ; National Science & Technology Major Project on 'Key New Drug Creation and Manufacturing Program'[2009ZX09103-062] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| WOS记录号 | WOS:000307601300029 |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/277982]  |
| 专题 | 药理学第一研究室 中科院受体结构与功能重点实验室 新药研究国家重点实验室 药物化学研究室 |
| 通讯作者 | Cao, Yuqing |
| 作者单位 | 1.Chinese Acad Sci, SIMM, SOMCL, Shanghai 201203, Peoples R China 2.Hebei Univ, Coll Pharm, Baoding 071002, Peoples R China; 3.Chinese Acad Sci, SIMM, State Key Lab Drug Res, Shanghai 201203, Peoples R China; |
| 推荐引用方式 GB/T 7714 | Ye, Na,Xu, Xiangtao,Li, Fuying,et al. Investigation on the oxidation of aryl oxiranylmethanols and the synthesis of 2-aryl-N-thiazolyl-oxirane-2-carboxamides as gincokinase activators[J]. TETRAHEDRON LETTERS,2012,53(35):4738-4742. |
| APA | Ye, Na.,Xu, Xiangtao.,Li, Fuying.,Ning, Mengmeng.,Liu, Zhiqing.,...&Zhang, Ao.(2012).Investigation on the oxidation of aryl oxiranylmethanols and the synthesis of 2-aryl-N-thiazolyl-oxirane-2-carboxamides as gincokinase activators.TETRAHEDRON LETTERS,53(35),4738-4742. |
| MLA | Ye, Na,et al."Investigation on the oxidation of aryl oxiranylmethanols and the synthesis of 2-aryl-N-thiazolyl-oxirane-2-carboxamides as gincokinase activators".TETRAHEDRON LETTERS 53.35(2012):4738-4742. |
入库方式： OAI收割
来源：上海药物研究所
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