21084-27-5Relevant academic research and scientific papers
Visible Light-Mediated [2 + 2] Cycloaddition Reactions of 1,4-Quinones and Terminal Alkynes
Sultan, Shaista,Bhat, Muneer-Ul-Shafi,Rizvi, Masood Ahmad,Shah, Bhahwal Ali
, p. 8948 - 8958 (2019/08/12)
A single-step synthesis of 4-hydroxy-functionalized bi-aryl and aryl/alkyl ketones via oxidative coupling of terminal alkynes with benzoquinones is reported. Furthermore, with naphthoquinones, owing to the cross-resonance of carbonyl with the aromatic ring, alkene-alkyne cycloaddition is more favored to give four-membered carbocyclic adducts, thereby precluding the requirement of preactivated alkynes.
Tandem catalysis: Access to ketones from aldehydes and arylboronic acids via rhodium-catalyzed addition/oxidation
Mora, Guilhem,Darses, Sylvain,Genet, Jean-Pierre
, p. 1180 - 1184 (2008/09/16)
Direct cross-coupling reactions of aromatic aldehydes with arylboronic acids afforded ketones in high yields and under mild conditions in the presence of a rhodium catalyst, acetone and a base. This new reaction, involving a formal aldehyde C-H bond activation, is believed to proceed via a tandem process involving addition of the organometallic species to the aldehyde followed by oxidation by β-hydride transfer.
Synthesis and structure-activity relationship for new series of 4-phenoxyquinoline derivatives as specific inhibitors of platelet-derived growth factor receptor tyrosine kinase
Kubo, Kazuo,Ohyama, Shin-Ichi,Shimizu, Toshiyuki,Takami, Atsuya,Murooka, Hideko,Nishitoba, Tsuyoshi,Kato, Shinichiro,Yagi, Mikio,Kobayashi, Yoshiko,Iinuma, Noriko,Isoe, Toshiyuki,Nakamura, Kazuhide,Iijima, Hiroshi,Osawa, Tatsushi,Izawa, Toshio
, p. 5117 - 5133 (2007/10/03)
We discovered a new series of 4-phenoxyquinoline derivatives as potent and selective inhibitors of the platelet-derived growth factor receptor (PDGFr) tyrosine kinase. We researched the highly potent and selective inhibitors on the basis of both PDGFr and epidermal growth factor receptor (EGFr) inhibitory activity. First, we found a compound, Ki6783 (1), which inhibited PDGFr autophosphorylation at 0.13 μM, but it did not inhibit EGFr autophosphorylation at 100 μM. After extensive explorations, we found the two desired compounds, Ki6896 (2) and Ki6945 (3), which are substituted by benzoyl and benzamide at the 4-position of the phenoxy group on 4-phenoxyquinoline, respectively. These inhibitory activities were 0.31 and 0.050 μM, respectively, but neither of them inhibited EGFr autophosphorylation at 100 μM. We further investigated the profile of both compounds toward various tyrosine and serine/threonine kinases. The three compounds specifically inhibited PDGFr rather than the other kinases.
Quinoline and quinazoline derivatives inhibiting platelet-derived growth factor receptor autophosphorylation and pharmaceutical compositions containing the same
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, (2008/06/13)
The present invention relates to novel quinoline derivatives and quinazoline derivatives represented by the following formula (I): STR1 [wherein R 1 and R 2 are each independently H or C 1 -C 4 -alkyl, or R 1 and R 2 together form C 1 -C 3 -alkylene, X is O, S or CH 2, W is CH or N, and Q is a substituted aryl group or substituted heteroaryl group] and their pharmaceutically acceptable salts, having platelet-derived growth factor receptor autophosphorylation inhibitory activity, to pharmaceutical compositions containing these compounds, and to methods for the treatment of diseases associated with abnormal cell growth such as tumors.
Polymerisation and Related Reactions involving Nucleophilic Aromatic Substitution. Part 1. The Rates of Reaction of Substituted 4-Halogenobenzophenones with the Potassium Salts of Substituted 4-Hydroxybenzophenones
Ridd, John H.,Yousaf, Taher I.,Rose, John B.
, p. 1729 - 1734 (2007/10/02)
The rate of displacement of fluorine from 4'-X,4-fluorobenzophenones by the potassium salts of 4'-X,4-hydroxybenzophenones (X = CF3, Cl, F, H, OPh, and OMe) has been studied at 175-225 deg C in diphenyl sulphone as solvent.Comparison with the corresponding rate of displacement of chlorine indicates that the reaction is a bimolecular nucleophilic aromatic substitution.The reaction obeys the Hammett equation using normal ? values for substitution in both the substrate (ρ 1.19) and the phenolate (ρ -0.53).There is also a marked salt effect on the reaction rate and this has been included with the substituent constants in a general equation for the calculation of rate coefficients.The effect of an O- substituent is more marked than would have been expected from the previous range of ? values ascribed to this substituent.
