38588-49-7Relevant academic research and scientific papers
Effective bimetallic composite catalysts for the synthesis of arylated furans and thiophenes in aqueous media
Bumagin, Nikolay A.,Petkevich, Sergey K.,Kletskov, Alexey V.,Alekseyev, Roman S.,Potkin, Vladimir I.
, (2019/08/12)
[Figure not available: see fulltext.] N-(4,6-Dimethylpyrimidin-2-yl)-5-phenylisoxazole-3-carboxamide was used as a ligand for obtaining bimetallic boron-containing heterogeneous catalysts Pd–Ni(Co)–B–L (Ni(Co):Pd = 9:1). The obtained composites were highl
Artificial Ligands of Streptavidin (ALiS): Discovery, Characterization, and Application for Reversible Control of Intracellular Protein Transport
Terai, Takuya,Kohno, Moe,Boncompain, Gaelle,Sugiyama, Shigeru,Saito, Nae,Fujikake, Ryo,Ueno, Tasuku,Komatsu, Toru,Hanaoka, Kenjiro,Okabe, Takayoshi,Urano, Yasuteru,Perez, Franck,Nagano, Tetsuo
supporting information, p. 10464 - 10467 (2015/09/28)
Artificial ligands of streptavidin (ALiS) with association constants of 106 M-1 were discovered by high-throughput screening of our chemical library, and their binding characteristics, including X-ray crystal structure of the streptavidin complex, were determined. Unlike biotin and its derivatives, ALiS exhibits fast dissociation kinetics and excellent cell permeability. The streptavidin-ALiS system provides a novel, practical compound-dependent methodology for repeated reversible cycling of protein localization between intracellular organella.
5-(Naphth-1-yl)- and 5-[(1,1'-biphenyl)-4-yl]isoxazole-3-carbaldehyde oximes: Synthesis, complexes with palladium, and application in catalysis
Potkin,Bumagin,Zelenkovskii,Petkevich,Livantsov,Golantsov
, p. 1782 - 1792 (2015/01/08)
1-(Naphth-1-yl)- and 1-[(1,1'-biphenyl)-4-yl-3,4,4-trichloro-3-buten-1-ones were synthesized by acylation of naphthalene and biphenyl with 3,4,4-trichloro-3-butenoyl chloride. Further reaction with hydroxylamine led to 5-(naphth-1-yl)- and 5-[(1,1'-biphen
An effective activation of palladium phosphine complexes in aqueous phase reactions of hetero-aromatic boronic acids with aryl halides
Bumagin,Veselov,Belov
, p. 19 - 25 (2014/05/06)
We have developed a simple and effective method for the activation of palladium phosphine complexes in the Suzuki reaction (TON up to 9800, TOF up to 58800 h-1) by selecting an aqueous reaction medium instead of organic solvents. This method wa
5-substituted-2-furaldehydes: A synthetic protocol utilizing an organozinc route
Kim, Seung-Hoi,Rieke, Reuben D.
, p. 1984 - 1993 (2013/04/10)
Facile synthetic routes for the preparation of a wide range of 5-substituted 2-furaldehydes have been revealed. They were accomplished through either Pd-catalyzed cross-coupling reaction of various aryl- and heteroarylzinc halides with 5-bromo-2-furaldehyde or utilization of a new organozinc reagent, 5-(1,3-dioxolan-2-yl)-2-furanylzinc bromide, which was easily prepared by the direct insertion of highly active zinc to 2-(5-bromofuran-2-yl-1,3-dioxolane. Of special note is the uniqueness of using a new organozinc reagent, representing a first example of the direct synthesis of the corresponding organozinc halide. The subsequent coupling reactions in various types of reaction conditions led to the formation of somewhat different furan derivatives. It is also of significance that all of the cross-coupling reactions were carried out under mild conditions.
Room-temperature Suzuki-Miyaura coupling of heteroaryl chlorides and tosylates
Yang, Junfeng,Liu, Sijia,Zheng, Jian-Feng,Zhou, Jianrong
supporting information, p. 6248 - 6259,12 (2020/09/16)
Suzuki-Miyaura coupling of heteroaryls is an important method for the preparation of compound libraries for medicinal chemistry and materials research. Although many catalysts have been developed, none of them have been generally applicable to the coupling reactions of heteroaryl chlorides and tosylates at room temperature. We discovered that a catalyst combination of Pd(OAc)2 and XPhos (2-dicyclohexylphosphanyl-2',4',6'- triisopropylbiphenyl) could efficiently catalyze these couplings. Besides the choice of catalyst, the use of hydroxide bases in an aqueous alcoholic solvent was essential for fast couplings. These conditions promoted fast release of active catalyst (XPhos)Pd0, and accelerated the transmetalation in the catalytic cycle. Most of the major families of heteroaryl chlorides (31 examples) and tosylates (17 examples) reached full conversion within minutes to hours at room temperature. The method could be easily scaled up for gram-scale synthesis. Furthermore, we examined the relative reactivity of coupling partners in whole reactions. Electron-rich heteroaryl chlorides and tosylates reacted more slowly than electron-deficient ones, in the order of indole, pyrrole furan, thiophene > pyridine. Similarly, electron-deficient arylboronic acids were less reactive than electron-neutral and electron-rich ones. The reactivity trends from this study can help to choose appropriate coupling partners for Suzuki reactions.
A convenient synthesis of 5-aryl- and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of organozincs
Kim, Seung-Hoi,Rieke, Reuben D.
experimental part, p. 2657 - 2659 (2010/06/19)
An efficient synthetic route for the preparation of 5-heteroaryl- and 5-aryl-2-furaldehydes has been developed. It has been accomplished by the palladium(0)-catalyzed cross-coupling reaction of heteroarylzinc and arylzinc reagents with 5-bromo-2-furaldehyde under very mild conditions.
Low catalyst loading ligand-free palladium-catalyzed direct arylation of furans: An economically and environmentally attractive access to 5-arylfurans
Dong, Jia Jia,Roger, Julien,Pogan, Franc,Doucet, Henri
experimental part, p. 1832 - 1846 (2011/03/18)
The direct 5-arylation of furans at very low catalyst loading using Pd(OAc)2 as catalyst without added ligand proceed in high yields. Turnover numbers up to 10000 have been obtained for the coupling of several activated aryl bromides. A wide ra
Synthetic inhibitors of cytochrome P-450 2A6: Inhibitory activity, difference spectra, mechanism of inhibition, and protein cocrystallization
Yano, Jason K.,Denton, Travis T.,Cerny, Matthew A.,Zhang, Xiaodong,Johnson, Eric F.,Cashman, John R.
, p. 6987 - 7001 (2007/10/03)
A series of 3-heteroaromatic analogues of nicotine were synthesized to delineate structural and mechanistic requirements for selectively inhibiting human cytochrome P450 (CYP) 2A6. Thiophene, substituted thiophene, furan, substituted furan, acetylene, imidazole, substituted imidazole, thiazole, pyrazole, substituted pyrazole, and aliphatic and isoxazol moieties were used to replace the N-methylpyrrolidine ring of nicotine. A number of potent inhibitors were identified, and several exhibited high selectivity for CYP2A6 relative to CYP2E1, -3A4, -2B6, -2C9, -2C19, and -2D6. The majority of these inhibitors elicited type II difference spectra indicating the formation of a coordinate covalent bond to the heme iron. The majority of inhibitors were reversible inhibitors although several mechanism-based inactivators were identified. Most of the inhibitors were also relatively metabolically stable. X-ray crystal structures of CYP2A6 cocrystallized with three furan analogues bearing methanamino side chains indicated that the amine side chain coordinated to the heme iron. The pyridyl moiety was positioned to accept a hydrogen bond from Asn297, and all three inhibitors exhibited orthogonal aromatic-aromatic interactions with protein side chains. For comparison, the cocrystal structure of 4,4′-dipyridyl disulfide was also obtained and showed that the pyridine moiety could assume a different orientation than that observed for the 3-heteroaromatic pyridines examined. For the 3-heteroromatic pyridines, N-methyl and N,N-dimethyl amino groups increased the apparent Ki and distorted helix I of the protein. Substitution of a phenyl ring for the pyridyl ring also increased the apparent Ki, which is likely to reflect the loss of the hydrogen bonding interaction with Asn297. In contrast, inhibitory potency for other P450s was increased, and the selectivity of the phenyl analogues for CYP2A6 was decreased relative to the pyridyl compounds. The results suggest that inhibitors that compliment the active site features of CYP2A6 can exhibit significant selectivity for CYP2A6 relative to other human liver drug-metabolizing P450s.
Furan-2-ylmethylene thiazolidinediones as novel, potent, and selective inhibitors of phosphoinositide 3-kinase γ
Pomel, Vincent,Klicic, Jasna,Covini, David,Church, Dennis D.,Shaw, Jeffrey P.,Roulin, Karen,Burgat-Charvillon, Fabienne,Valognes, Delphine,Camps, Montserrat,Chabert, Christian,Gillieron, Corinne,Fran?on, Bernard,Perrin, Dominique,Leroy, Didier,Gretener, Denise,Nichols, Anthony,Vitte, Pierre Alain,Carboni, Susanna,Rommel, Christian,Schwarz, Matthias K.,Rückle, Thomas
, p. 3857 - 3871 (2007/10/03)
Class I phosphoinositide 3-kinases (PI3Ks), in particular PI3Kγ, have become attractive drug targets for inflammatory and autoimmune diseases. Here, we disclose a novel series of furan-2-ylmethylene thiazolidinediones as selective, ATP-competitive PI3Kγ i
