65171-10-0Relevant 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
, 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).
A short synthesis of biologically active lignan analogues
Kamlage,Sefkow,Pool-Zobel,Peter
, p. 331 - 332 (2007/10/03)
β-Benzyl-γ-butyrolactones were synthesized in four transition metal catalysed reactions from butynediol, and alkylated to afford new, biologically active lignan analogues.
Radical cyclisation based approach to lignans. Synthesis of 4-arylmethyldihydrofuran-2-ones
Srikrishna,Danieldoss
, p. 2357 - 2364 (2007/10/03)
Bromoacetalisation of the cinnamyl alcohols 7a-d, obtained from the corresponding benzaldehydes, generated the bromoacetals 10a-d. The 5-exo trig radical cyclisation of the bromoacetals 10a-d followed by one step hydrolysis-oxidation of the resulting cyclic acetals 11a-d furnished the title compounds 6a-d, respectively, well-established intermediates of a variety of lignans.
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
Stereoselective syntheses of cis- and trans-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignans: New syntheses of (±)-trachelogenin and (±)-guayadequiol
Moritani, Yasunori,Fukushima, Chiaki,Ukita, Tatsuzo,Miyagishima, Toshikazu,Ohmizu, Hiroshi,Iwasaki, Tameo
, p. 6922 - 6930 (2007/10/03)
Cis- and trans-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignans 1a,d-g and 2a,c,d were stereoselectively synthesized in good yields based on the electrophilic addition to the metal enolate of α-benzyl-γ-butyrolactone derivatives 1l-o and 3 as a key step. This method was applied to the syntheses of (±)-trachelogenin and (±)-guayadequiol, representative examples of the trans- and cis-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignan series.
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.
