86653-16-9Relevant articles and documents
Design and synthesis of novel arctigenin analogues for the amelioration of metabolic disorders
Duan, Shudong,Huang, Suling,Gong, Jian,Shen, Yu,Zeng, Limin,Feng, Ying,Ren, Wenming,Leng, Ying,Hu, Youhong
, p. 386 - 391 (2015/04/27)
Analogues of the natural product (-)-arctigenin, an activator of adenosine monophosphate activated protein kinase, were prepared in order to evaluate their effects on 2-deoxyglucose uptake in L6 myotubes and possible use in ameliorating metabolic disorders. Racemic arctigenin 2a was found to display a similar uptake enhancement as does (-)-arctigenin. As a result, the SAR study was conducted utilizing racemic compounds. The structure-activity relationship study led to the discovery of key substitution patterns on the lactone motif that govern 2-deoxyglucose uptake activities. The results show that replacement of the para-hydroxyl group of the C-2 benzyl moiety of arctigenin by Cl has a pronounced effect on uptake activity. Specifically, analogue 2p, which contains the p-Cl substituent, stimulates glucose uptake and fatty acid oxidation in L6 myotubes.
Erratum: Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones (Journal of the American Chemical Society (2012) 134 (17023-17026) DOI:10.1021/ja309262f)
Zhou, Lin,Liu, Xiaohua,Ji, Jie,Zhang, Yuheng,Hu, Xiaolei,Lin, Lili,Feng, Xiaoming
supporting information, p. 20208 - 20208 (2013/02/23)
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Comparing the stereoselective biooxidation of cyclobutanones by recombinant strains expressing bacterial baeyer - Villiger monooxygenases
Rudroff, Florian,Rydz, Joanna,Ogink, Freek H.,Fink, Michael,Mihovilovic, Marko D.
, p. 1436 - 1444 (2008/09/17)
Microbial Baeyer - Villiger oxidation of representative prochiral ketones with a cyclobutanone structural motif was investigated using a collection of eight monooxygenases of different bacterial origin. This platform of enzymes is able to perform stereoselective biotransformations on an array of structurally diverse substrates. With several ketone precursors, biooxidations yielded enantiocomplementary butyrolactones as key intermediates for the synthesis of natural products and bioactive compounds. The microbial Baeyer - Villiger oxidation allows a facile and rapid entry to several compound classes in a desymmetrization reaction upon de novo generation of chirality.
