- Design and synthesis of novel arctigenin analogues for the amelioration of metabolic disorders
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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.
- Duan, Shudong,Huang, Suling,Gong, Jian,Shen, Yu,Zeng, Limin,Feng, Ying,Ren, Wenming,Leng, Ying,Hu, Youhong
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supporting information
p. 386 - 391
(2015/04/27)
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- Carboxylic acids and the esters thereof, pharmaceutical compositions thereto and processes for the preparation thereof
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The present invention relates to carboxylic acids and esters of general formula wherein Ar, R, R1, X1, X3, X4, Y and Y1 are defined as in claim 1, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, pharmaceutical compositions containing these compounds, the use thereof and processes for the preparation thereof, as well as the use thereof for the production and purification of antibodies and as labelled compounds in RIA and ELISA assays and as diagnostic or analytical aids in neurotransmitter research.
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Page 46percent
(2008/06/13)
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- Simple synthesis of trans-α,β-dibenzyl-γ-butyrolactone lignans by diastereoselective reduction of α-benzylidene-β-benzyl-γ-butyralactones using NaBH4-NiCl2
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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
- Moritani,Fukushima,Miyagishima,Ohmizu,Iwasaki
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p. 2281 - 2286
(2007/10/03)
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- PREPARATION OF (R)-VERATRYL- AND (R)-(3-METHOXYBENZYL)SUCCINATES
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LP-catalyzed hydrolyses of 4-cyanomethyl 1-methyl veratryl- and (3-methoxy benzyl)succinates lead in high optical yield to the corresponding (R)-butanoic acids.HLE-catalyzed hydrolyses of various methyl and cyanomethyl veratrylsuccinates lead to mixtures
- Barnier, Jean-Pierre,Blanco, Luis,Guibe-Jampel, Eryka,Rousseau, Gerard
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p. 5051 - 5058
(2007/10/02)
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- Oxidative Coupling of Lignans. III. Non-Phenolic Oxidative Coupling of Deoxypodorhizon and Related Compounds
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Oxidative coupling of deoxypodorhizon (4) with thallium(III) oxide and trifluoroacetic acid may be controlled to give either deoxyisopodophyllotoxin (14) or isostegane (16).These results and those with related non-phenolic substances indicate that the aromatic substituents of the parent diarylbutane play an important role in determining the outcome of oxidative coupling.
- Cambie, Richard C.,Craw, Peter A.,Rutledge, Peter S.,Woodgate, Paul D.
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p. 897 - 918
(2007/10/02)
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- (R)-(+)-β-VERATRYL-γ-BUTYROLACTONE, A NEW KEY-INTERMEDIATE FOR THE ASYMMETRIC SYNTHESIS OF VARIOUS LIGNANS
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Methyl α-veratrylhemisuccinate was resolved into its (R)-(+) and (S)-(-) antipodes by (S)-(-) and (R)-(+)-α-methylbenzylamine respectively.Calcium borohydride reduction of the (R)-(+)-hemiester afforded (R)-(+)-β-veratryl-γ-butyrolactone.The latter was us
- Brown, Eric,Daugan, Alain
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p. 3719 - 3722
(2007/10/02)
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- LE TETRAKIS(TRIFLUOROACETATE) DE RUTHENIUM(IV), NOUVEAU CATALYSEUR A TEMPERATURE AMBIANTE DU COUPLAGE BIARYLIQUE OXIDANT NON PHENOLIQUE-PREMIERE SYNTHESE TOTALE BIOMIMETIQUE DU NEOISOSTEGANE-
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In situ generated Ruthenium(IV) tetrakis(trifluoroacetate) -a new organometallic reagent- was used in intramolecular non-phenolic oxydative biaryl coupling of dibenzylbutanolides, and an application to the first total synthesis of neoisostegane was perfor
- Landais, Y.,Robin, J.-P.
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p. 1785 - 1788
(2007/10/02)
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- Synthesis of Aryltetralin and Dibenzylbutyrolactone Lignans: (+/-)-Lintetralin, (+/-)-Phyltetralin, and (+/-)-Kusunokinin
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Application of a general synthetic pathway for aryltetralin and dibenzylbutyrolactone lignans, starting from the lithium enolate of 3-(3,4-dimethoxybenzyl)butyrolactone (1) led to syntheses of (+/-)-lintetralin (4), (+/-)-phyltetralin (5), (+/-)-isogalcat
- Ganeshpure, Pralhad A.,Stevenson, Robert
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p. 1681 - 1684
(2007/10/02)
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