84755-36-2Relevant academic research and scientific papers
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
supporting information, 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.
Synthesis of dibenzylbutyrolactone lignans: Total synthesis of arctigenin, pluviatolide and haplomyrfolin by tandem conjugate addition
Mitra, Jayati,Mitra, Alok Kumar
, p. 953 - 956 (2007/10/02)
The total synthesis of three dibenzylbutyrolactone lignans, arctigenin, pluviatolide and haplomyrfolin has been carried out by tandem cnjugate addition of dithiane carbanions to but-2-en-4-olide and substituted benzyl bromides leading to the formation of key intermediates which subsequently underwent debenzylation and desulphurisation.
