119138-93-1Relevant 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 and cytotoxicity of racemic isodeoxypodophyllotoxin analogues with isoprene-derived side chains
Zhao, Yu,Feng, Ju Hong,Ding, Hong Xia,Xiong, Yi,Cheng, Christopher H. K.,Hao, Xiao Jiang,Zhang, Yong Min,Pan, Yuan Jiang,Gueritte, Francoise,Wu, Xiu Mei,Bai, Hua,Stoeckigt, Joachim
, p. 1145 - 1152 (2008/09/21)
A series of isodeoxypodophyllotoxin (5) analogues, 26-38, with various isoprene-derived side chains at the E-ring were designed and synthesized. For comparison, compound 39, with a benzyloxy group on the E-ring, and six D-ring opened analogues, 40-45, were also prepared. All the synthetic compounds were evaluated for their cytotoxic activities in vitro against seven cultured human tumor cell lines. Compounds 27, 43, and 44 were more cytotoxic than etoposide on BEL-7404, A549, and HL-60 cell lines, respectively. However, none of the synthetic isodeoxypodophyllotoxins were more cytotoxic than podophyllotoxin (1).
Simple synthesis of trans-α,β-dibenzyl-γ-butyrolactone lignans by diastereoselective reduction of α-benzylidene-β-benzyl-γ-butyralactones using NaBH4-NiCl2
Moritani,Fukushima,Miyagishima,Ohmizu,Iwasaki
, p. 2281 - 2286 (2007/10/03)
trans-α,β-Dibenzyl-γ-butyrolactone lignans were synthesized by stereoselective reduction of α-benzylidene-β-benzyl-γ-butyrolactones using NaBH4-NiCl2. The reduction is found to proceed via conjugate addition of a hydride to an α-benz
SYNTHESES TOTALES ET ETUDES DE LIGNANES BIOLOGIQUEMENT ACTIFS-I. APPLICATION DE LA REACTION D'ULLMANN A LA SYNTHESE DE BIARYLES PRECURSEURS DE LIGNANES BISBENZOCYCLOOCTADIENES
Brown, Eric,Robin, Jean-Pierre,Dhal, Robert
, p. 2569 - 2580 (2007/10/02)
Several biaryls bearing various substituents on both rings were synthesized in a preparativ fashion, and in yields up to 88percent by a technical improvement on the classical Ullmann reaction.All these biaryls bear reactive functional groups (i.e. formyl, methoxycarbonyl, dimethoxycarbonylpropyl and butanolidylmethyl) in both the o and o' positions.The biaryls 9, 13, 21 and 26-33 are plausible synthons for bisbenzocyclooctadiene lignans such as schizandrin and steganacin.
