2845-83-2Relevant articles and documents
Novel Potent Selective Orally Active S1P5 Receptor Antagonists
Ma, Bin,Guckian, Kevin M.,Liu, Xiao-Gao,Yang, Chunhua,Li, Bing,Scannevin, Robert,Mingueneau, Micha?l,Drouillard, Annabelle,Walzer, Thierry
supporting information, (2021/02/01)
S1P5 is one of the five sphingosine-1-phosphate (S1P) receptors which play important roles in immune and CNS cell homeostasis, growth, and differentiation. Little is known about the effect of modulation of S1P5 due to the lack of S1P5 specific modulators with suitable druglike properties. Here we describe the discovery and optimization of a novel series of potent selective S1P5 antagonists and the identification of an orally active brain-penetrant tool compound 15.
One-pot formal synthesis of biorenewable terephthalic acid from methyl coumalate and methyl pyruvate
Lee, Jennifer J.,Kraus, George A.
, p. 2111 - 2116 (2014/04/17)
Diverse functionalized aromatic compounds are constructed from captodative dienophiles with exclusive regioselectivity. 100% biorenewable dimethyl terephthalate (DMT) from methyl coumalate and methyl pyruvate is achieved in a one-pot, Diels-Alder/decarboxylation/elimination sequence in nearly quantitative yield. The DMT system is solvent-free and purification is accomplished through recrystallization. DMT hydrolysis reveals the co-monomer terephthalic acid (TPA) as a bio-based drop-in replacement for the polymer industry, avoiding harsh oxidation and petrochemicals. the Partner Organisations 2014.
S1P MODULATING AGENTS
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Page/Page column 40, (2014/08/19)
Compounds of formula (I) can modulate the activity of one or more S 1P receptors. Sphingosine 1-phosphate (S IP) is a lysophospholipid mediator that evokes a variety of cellular responses by stimulation of five members of the endothelial cell differentiation gene (EDG) receptor family, namely S1P1, S1P2, S1P3, S1P4, and S1P5 (formerly EDG1, EDG5, EDG3, EDG6 and EDG8). The EDG receptors are G-protein coupled receptors (GPCRs) and on stimulation propagate second messenger signals via activation of heterotrimeric G-protein alpha (Ga.) subunits and beta-gamma (G()y) dimers.
BICYCLIC ARYL SPHINGOSINE 1-PHOSPHATE ANALOGS
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Page/Page column 138, (2011/02/24)
Compounds that have agonist activity at one or more of the SlP receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at SlP receptors.
The Reaction of 3-(1-Imidazolyl)-2-alken-1-ones with Nucleophiles
Kashima, C.,Tajima, T.,Shimizu, M.,Omote, Y.
, p. 1325 - 1328 (2007/10/02)
Generally 3-hetero-substituted 2-alken-1-ones were prepared from 1,3-alkanediones, 3-chloro-2-alken-1-ones, or conjugated ynones.The preparation of 3-hetero-substituted 2-alken-1-ones was subjected to some limitations by these methods.By the reaction of 3-(1-imidazolyl)-2-alken-1-ones (I) and 3-(3-oxo-1-alkenyl)-1-methylimidazolium iodides (II) with nucleophiles, 3-hetero-substituted 2-alken-1-ones could be obtained regioselectively in good yield under mild conditions.These results suggested that compounds I and II were concluded to be useful intermediates for the organic synthesis.
The Allopolarization Principle and its Applications, IV. Substituent Effects in the Methylation of Enolate Anions
Gompper, Rudolf,Vogt, Hans-Hubert
, p. 2866 - 2883 (2007/10/02)
The ratio of O- and C-methylated products in the reaction of the sodium salts of acetophenones 1, propiophenones 3, phenylacetones 5, β-dicarbonyl compounds 12, α-cyanocarbonyl compounds 13, acetaldehyde, propionaldehyde, and diethylketone with dimethyl sulfate, methyl iodide, and trimethyl phosphate in HMPTA has been determined with regard to the effect of substituents.In some cases the influence of solvents, concentration and temperature has also been studied.
The Allopolarization Principle and its Applications, VI. The Alkylation of Enolate Anions: Polarity and Regioselectivity
Gompper, Rudolf,Vogt, Hans-Hubert,Wagner, Hans-Ulrich
, p. 1644 - 1652 (2007/10/02)
The O/C methylation ratio in the reaction of sodium enolates with dimethylsulfate depends on the polar (electronic) effect of substituents.The relative ?-charge density Px/y = lx/ly can be used as a measure for the polarity of ambifunctional anions; in case of enolate anions PO/C = lO/lC.The change of the regioselectivity Sf = log QO/QC in the alkylation of enolates is a function of a change in the polarity PO/C; ΔSf=f(ΔPx/y).The polar effect of substituents influences the charge control during the alkylation process via a change of the polarity of the enolate system: The higher the polarity of the anion, the stronger the charge control and the higher the yield of enol ether (O-alkylation). - Keywords: Alkylation, Enolate Anions