26207-06-7Relevant 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.
Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts
Ellwart, Mario,Gensch, Tobias,Han, Seo-Jung,Lin, Hsin-Hui,Miró, Javier,Sigman, Matthew S.,Toste, F. Dean
supporting information, p. 6390 - 6399 (2020/04/27)
Herein we report the first highly enantioselective allenoate-Claisen rearrangement using doubly axially chiral phosphate sodium salts as catalysts. This synthetic method provides access to β-amino acid derivatives with vicinal stereocenters in up to 95percent ee. We also investigated the mechanism of enantioinduction by transition state (TS) computations with DFT as well as statistical modeling of the relationship between selectivity and the molecular features of both the catalyst and substrate. The mutual interactions of charge-separated regions in both the zwitterionic intermediate generated by reaction of an amine to the allenoate and the Na+-salt of the chiral phosphate leads to an orientation of the TS in the catalytic pocket that maximizes favorable noncovalent interactions. Crucial arene-arene interactions at the periphery of the catalyst lead to a differentiation of the TS diastereomers. These interactions were interrogated using DFT calculations and validated through statistical modeling of parameters describing noncovalent interactions.
S1P MODULATING AGENTS
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Page/Page column 41, (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 139-140, (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.
Synthesis of 2-naphthols via carbonylative stille coupling reaction of 2-bromobenzyl bromides with tributylallylstannane followed by the heck reaction
Dai, Yao,Feng, Xiujuan,Liu, Hesong,Jiang, Hua,Bao, Ming
, p. 10068 - 10077 (2012/02/04)
A method for the synthesis of 2-naphthols 4 is described. The carbonylative Stille coupling reactions of 2-bromobenzyl bromides with tributylallylstannane to produce 2-bromobenzyl β,γ-unsaturated ketones 2 in satisfactory to excellent yields has been achieved. The isomerization of 2-bromobenzyl β,γ-unsaturated ketones 2 can readily occur under basic conditions to generate 2-bromobenzyl α,β-unsaturated ketones 3. The 2-bromobenzyl α,β-unsaturated ketones 3 can be transformed into 2-naphthols 4 via intramolecular Heck reaction in satisfactory to good yields (Figure presented).
REACTION OF PHENOLS AND THEIR DERIVATIVES WITH AROMATIC COMPOUNDS IN THE PRESENCE OF ACIDIC AGENTS X. ROTATIONAL ISOMERISM IN THE SERIES OF 2-METHOXY-1-NAPHTHALENONIUM IONS
Repinskaya, I. B.,Shakirov, M. M.,Koltunov, K. Yu.,Koptyug, V. A.
, p. 778 - 784 (2007/10/02)
It was shown by 13C NMR spectroscopy that 4-X-2-methoxy-1-naphthalenonium ions (X=H, Cl, CH3, C6H5), generated in the HSO3F-SO2FCl medium, exist as Z and E isomers due to restricted rotation about the C-O partial double bond.It is not possible to detect Z, E isomerism in the corresponding 4-X-2-hydro-1-naphthalenonium ions or in the 2,4-dimethoxy- and 1-chloro-2-methoxy-1-naphthalenonium ions.
Studies on Furano Compounds: Part XLVIII - Syntheses of 2,5-Dimethyl- and 2-Ethyl-5-methylnaphthofurans
Chatterjea, Jnanendra N.,Lal, Siddheshwar,Jha, Udar,Carnduff, John
, p. 264 - 267 (2007/10/02)
4-Methyl-2-naphthol has been synthesised unambiguously and converted into 2,5-dimethyl- (4) and 2-ethyl-5-methylnaphthofurans (5) through a series of reactions thereby confirming that Vilsmeier formylation of 2-alkylnaphthofurans occurs at position-5.
Arynic Condensations of Ketone Enolates. 15. New Synthetic Applications of the Condensation of α,β-Unsaturated Ketone Enolates on Benzyne
Essiz, Munir,Guillaumet, Gerald,Brunet, Jean-Jacques,Caubere, Paul
, p. 240 - 246 (2007/10/02)
Arynic condensations of both cyclic and acyclic α,β-unsaturated ketone enolates are studied.First, condensation of substituted cyclohexenone enolates with benzyne leads to a new class of cyclobutanic alcohols 6.Ring opening of 6 under basic conditions is described as a good means of synthesizing benzocyclooctadienones 10 and 19, and, in appropriate cases, benzocyclooctenediones of type 12.Thermal dehydration of 6 affords 1,3-disubstituted naphthalenes in good yields.Second, condensations of a few acyclic α,β-unsaturated ketone enolates with benzyne are shown to be of synthetic usefulness; depending on the substituents on both sides of the carbonyl group, these condensations may lead either to substituted naphthalenes or to phenyl ketones or tetralones.
