Jump to main content
Jump to site search

Issue 35, 2014
Previous Article Next Article

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 PPARγ modulator

Author affiliations

Abstract

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 PPARγ modulator was also demonstrated. The results from biological evaluation showed that compound 6 had a partial PPARγ agonistic activity and a strong PPARγ 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.

Graphical abstract: 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 PPARγ modulator

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 26 Mar 2014, accepted on 09 May 2014 and first published on 09 May 2014


Article type: Paper
DOI: 10.1039/C4OB00637B
Citation: Org. Biomol. Chem., 2014,12, 6831-6836
  •   Request permissions

    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 PPARγ modulator

    J. Shi, G. Zhao, X. Wang, H. E. Xu and W. Yi, Org. Biomol. Chem., 2014, 12, 6831
    DOI: 10.1039/C4OB00637B

Search articles by author