Document Detail


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.
MedLine Citation:
PMID:  24937203     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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 as a novel PPARγ modulator was also demonstrated. The results from biological evaluation showed that compound 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.
Authors:
Jingjing Shi; Guanguan Zhao; Xiaowei Wang; H Eric Xu; Wei Yi
Related Documents :
10739063 - Organochlorine compounds in the gulf of bothnia: sediment and benthic species.
23151283 - Palladium catalyzed one-pot sequential suzuki cross-coupling-direct c-h functionalizati...
17443183 - Regioselective one-pot protection of carbohydrates.
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2014-6-17
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  -     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2014 Jun 
Date Detail:
Created Date:  2014-6-17     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Evidence for global cooling in the Late Cretaceous.
Next Document:  Central Nervous System Penetration and Effectiveness of Darunavir/Ritonavir Monotherapy.