Rhodium(III)-catalyzed regioselective C2-amidation of indoles with N-(2,4,6-trichlorobenzoyloxy)amides and its synthetic application to the development of a novel potential PPAR gamma modulator
文献类型：期刊论文
| 作者 | Shi, Jingjing2 ; Zhao, Guanguan2; Wang, Xiaowei2; Xu, H. Eric1,2; Yi, Wei2
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| 刊名 | ORGANIC & BIOMOLECULAR CHEMISTRY
 |
| 出版日期 | 2014 |
| 卷号 | 12期号:35页码:6831-6836 |
| ISSN号 | 1477-0520 |
| DOI | 10.1039/c4ob00637b |
| 文献子类 | Article |
| 英文摘要 | A new and efficient method for the direct regioselective C2-amidation of various functionalized indoles with several N-(2,4,6-trichlorobenzoyloxy) amides via Rh(III)-catalyzed C-H activation/N-O cleavage/C-N formation using the pyrimidyl group as a readily installable and removable directing group has been developed. With this method, a variety of valuable 2-amido indoles can be easily prepared under mild conditions with broad functional group tolerance and excellent region-/site-specificities. Application of this strategy to the synthesis of target compound 6 as a novel PPAR gamma modulator was also demonstrated. The results from biological evaluation showed that compound 6 had a partial PPAR gamma agonistic activity and a strong PPAR gamma binding affinity with an IC50 value of 120.0 nM, along with a less pronounced adipocyte differentiation ability compared to the currently marketed anti-diabetic drug rosiglitazone, suggesting that further development of such a compound might be of great interest. |
| WOS关键词 | C-H ACTIVATION ; N BOND FORMATION ; TYPE-2 DIABETES-MELLITUS ; CARBENOID FUNCTIONALIZATION ; PROTECTED ARYLAMINES ; SULFONYL AZIDES ; CYANIDE SOURCE ; AMIDATION ; AMINATION ; ARYLATION |
| 资助项目 | Jay and Betty Van Andel Foundation, Amway (China)[00000000] ; Chinese Postdoctoral Science Foundation[2012M511158] ; Chinese Postdoctoral Science Foundation[2013T60477] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| 出版者 | ROYAL SOC CHEMISTRY |
| WOS记录号 | WOS:000341024300011 |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/277273]  |
| 专题 | 药物靶标结构与功能中心 |
| 通讯作者 | Xu, H. Eric |
| 作者单位 | 1.Van Andel Res Inst, Lab Struct Sci, Program Struct Biol & Drug Discovery, Grand Rapids, MI 49503 USA 2.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, VARI SIMM Ctr,Ctr Struct & Funct Drug Targets, Shanghai 201203, Peoples R China; |
| 推荐引用方式 GB/T 7714 | Shi, Jingjing,Zhao, Guanguan,Wang, Xiaowei,et al. Rhodium(III)-catalyzed regioselective C2-amidation of indoles with N-(2,4,6-trichlorobenzoyloxy)amides and its synthetic application to the development of a novel potential PPAR gamma modulator[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2014,12(35):6831-6836. |
| APA | Shi, Jingjing,Zhao, Guanguan,Wang, Xiaowei,Xu, H. Eric,&Yi, Wei.(2014).Rhodium(III)-catalyzed regioselective C2-amidation of indoles with N-(2,4,6-trichlorobenzoyloxy)amides and its synthetic application to the development of a novel potential PPAR gamma modulator.ORGANIC & BIOMOLECULAR CHEMISTRY,12(35),6831-6836. |
| MLA | Shi, Jingjing,et al."Rhodium(III)-catalyzed regioselective C2-amidation of indoles with N-(2,4,6-trichlorobenzoyloxy)amides and its synthetic application to the development of a novel potential PPAR gamma modulator".ORGANIC & BIOMOLECULAR CHEMISTRY 12.35(2014):6831-6836. |
入库方式： OAI收割
来源：上海药物研究所
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