1474-92-6Relevant academic research and scientific papers
PYRAZINE DERIVATIVE
-
Paragraph 0085, (2017/04/04)
Provided is a novel pyrazine derivative represented by the following formula (I) or a pharmaceutically acceptable salt thereof, or a solvate thereof which is useful for treating or preventing diseases in which URAT1 is involved, including gout, hyperurice
Discovery of cell-active phenyl-imidazole Pin1 inhibitors by structure-guided fragment evolution
Potter, Andrew,Oldfield, Victoria,Nunns, Claire,Fromont, Christophe,Ray, Stuart,Northfield, Christopher J.,Bryant, Christopher J.,Scrace, Simon F.,Robinson, David,Matossova, Natalia,Baker, Lisa,Dokurno, Pawel,Surgenor, Allan E.,Davis, Ben,Richardson, Christine M.,Murray, James B.,Moore, Jonathan D.
scheme or table, p. 6483 - 6488 (2010/12/18)
Pin1 is an emerging oncology target strongly implicated in Ras and ErbB2-mediated tumourigenesis. Pin1 isomerizes bonds linking phospho-serine/threonine moieties to proline enabling it to play a key role in proline-directed kinase signalling. Here we report a novel series of Pin1 inhibitors based on a phenyl imidazole acid core that contains sub-μM inhibitors. Compounds have been identified that block prostate cancer cell growth under conditions where Pin1 is essential.
Preferred conformations of stabilized phosphorus ylides
Castaneda, Fernando,Terraza, Claudio A.,Bunton, Clifford A.,Gillitt, Nicholas D.,Garland, Maria T.
, p. 1973 - 1985 (2007/10/03)
The stabilized phosphorus ylides, Ph3P=(CO.R′)CO.OR; 1, R=Et, R′=CH2P+Ph3; 2, R=R'′=Me; 3, R=Et, R′=Me; 4, R=Pri; R′=Me; 5, R=But; R′=Me, adopt a near planar conformation in the crystal whi
Methyl, ethyl, isopropyl and tert-butyl 3-oxo-2-(triphenylphosphoranyl-idene)butyrates, a common pattern for a preferred conformation
Castaneda, Fernando,Terraza, Claudio A.,Garland, Maria Teresa,Bunton, Clifford A.,Baggio, Ricardo F.
, p. 180 - 184 (2007/10/03)
The crystal structures of four alkyl 3-oxo-2-(triphenyl-phosphoranylidene)butyrates, where the alkyl group is methyl (C23H21O3P·0.5C6H6), (II), ethyl (C24H23O3P), (III
Zinc promoted facile method for the acylation of ylides at α-carbon
Meshram,Reddy, Gondi Sudershan,Reddy, M. Muratidhar,Yadav
, p. 4107 - 4110 (2007/10/03)
Stabilised triphenylphosphonium ylides are acylated at the α-carbon with different acyl groups using zinc.
Synthesis of C-glycosyl isoxazoles and branched-chain enuloses from 2,3-O-isopropylidene-D-glyceraldehyde
Bá?ez Sanz,López Sastre,Pati?o Molina,Romero-ávila García
, p. 1331 - 1350 (2007/10/03)
The synthesis of 5-glycosyl isoxazoles with 3-alkyl-, 3-aryl, 3,4-dialkyl, 3-aryl-4-alkyl or 3-alkyl-4-bromo substituents is reported. Deoxyenuloses were obtained from reaction of 2,3-O-isopropylidene-D-glyceraldehyde and several phosphorus ylides, which contain a carbonyl group, by a Wittig reaction. C-glycosyl α,β-unsaturated ketones were obtained, with the polyhydroxylate chain lengthened by two or three carbon atoms. In the second phase the ketones were transformed into the corresponding C-glycosyl α,β-unsaturated ketoximes, leading to the C-glycosyl isoxazoles, which were converted into the title compounds via removal of the isopropylidene group of suitably protected carbohydrates. The solubility of the synthetized C-glycosyl isoxazoles were modified by free hydroxyl groups in such a way that their behaviour against certain viruses and their potential antiviral activity could be studied.
A STUDY OF REACTIONS BETWEEN CARBOETHOXYMETHYLENETRIPHENYLPHOSPHORANE AND ALKYL DIBROMIDES
Araya-Maturana, Ramiro,Castaneda, Fernando
, p. 165 - 172 (2007/10/02)
Carboethoxymethylenetriphenylphosphorane 1-reacts with 1,4-dibromobutane and 1,5-dibromopentane under transylidation conditions in refluxing anhydrous benzene affording the cyclization products, 1-carboethoxycyclopentyl and 1-carboethoxycyclohexyltriphenylphosphonium bromides, 6, which by alkaline hydrolysis produce the corresponding cycloalkylcarboxylic acids and esters.Phosphorane 1 and its phosphonium salt 5 formed in the transylidation step also lead to 3-carboethoxy-3-triphenylphosphoranyliden-2-oxopropanetriphenylphosphonium bromide (9) as a secondary reaction product.Key words: Phosphoranes; transylidation; alkylation; cycloalkyltriphenylphosphonium salst; cycloalkylcarboxylic acids.
Reactions of Ethoxycarbonylmethylene(triphenyl)phosphorane with some ortho-Quinones in the Presence of Triphenylphosphine, Alcohols and Acetic Anhydride
Nicolaides, Demetrios N.,Adamopoulos, Spyros G.,Lefkaditis, Demetrios A.,Litinas, Konstantinos E.,Tarantili, Petroula V.
, p. 283 - 290 (2007/10/02)
The reactions of ortho-quinones 1a, 1c and 1d with ylide 2 in the presence of triphenylphosphine afforded the ylides 11a, 11c and 11d and compound 12.The reactions of 1a and 1c with 2 in refluxing methanol or ethanol gave compounds 16 and 17 respectively, while the reactions of 1a-d with 2 in acetic anhydride yielded the acetates 18a, 18b, 18d and 19b, 19d, the furan derivative 24 and the ylide 25.Compounds 8 and 9 were also obtained in most of the above reactions.Wittig reactions of the ylides 11a, 11c with p-nitrobenzaldehyde and of ylide 2 with coumarins 8a and 29 resulted in compounds 14a, 14c, 26 and 30 respectively.The transformations of compounds 18, 19 into 8, 9 as well as of compound 26 into 28 were also studied.
Reaction of Triphenylphosphine Radical Cation with 1,3-Dicarbonyl Compounds: Electrochemical One-Step Preparation of Dioxomethylenetriphenylphosphoranes
Ohmori, Hidenobu,Maeda, Hatsuo,Tamaoka, Mie,Masui, Masaichiro
, p. 613 - 620 (2007/10/02)
Electrochemical oxidation of Ph3P (1) in MeCN in the presence of 1,3-dicarbonyl compounds, R1COCH2COR2 (3), with HClO4 as the supporting electrolyte resulted in the formation of the phosphonium salts, Ph3P+ -CH(COR1)COR2 ClO4- (4), provided that R1 and/or R2 is a phenyl group.On the other hand, electrolysis in CH2Cl2 with 2,6-lutidinium perchlorate gave the phosphoranes, Ph3P=C(COR1)COR2 (5), directly from 1 and 3 in fair to excellent yields: in this case, R1 or R2 need not necessarily be a phenyl group.Thus, the electrolysis is shown to be a convenient method to prepare 5 in a single step.Plausible processes for the formation of 4 and 5 are proposed, involving the reaction of electrochemically generated Ph3P+. with the enol form of 3 as the keystep.Keywords - triphenylphosphine; 1,3-dicarbonyl compound; dioxomethyltriphenylphosphonium perchlorate; dioxomethylenetriphenylphosphorane; electrochemical oxidation; constant current electrolysis
Aspects of the Mechanism of the Wittig Reaction Between Cyclic Anhydrides and Stabilized Phosphoranes
Abell, Andrew D.,Massy-Westropp Ralph A.
, p. 2077 - 2087 (2007/10/02)
It has been established that the Wittig reaction between cyclic anhydrides and ethoxycarbonylmethylenetriphenylphosphorane, a reaction used for the preparation of enol-lactones, proceeds via an acyclic intermediate acylated phosphorane for the three classes of anhydrides studied: succinic, maleic and phthalic.The formation of the acyclic intermediate can be irreversible or reversible, depending on the structure of the anhydride.The stereochemistry of the enol-lactones produced is not controlled by the initial reaction of the anhydride with the ylide but either during or after cyclization of the acyclic intermediate.Product formation appears to be under kinetic control with all the anhydrides studied.The influence of substituents in substituted phthalic anhydrides has been investigated
