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5413-05-8Relevant articles and documents
Synthetic Scope of Br?nsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate
Rahaman, Mizzanoor,Ali, M. Shahnawaz,Jahan, Khorshada,Hinz, Damon,Belayet, Jawad Bin,Majinski, Ryan,Hossain, M. Mahmun
, p. 6138 - 6147 (2021/05/06)
The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Br?nsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl-methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy.
DMT1 Inhibitors Kill Cancer Stem Cells by Blocking Lysosomal Iron Translocation
Turcu, Andreea L.,Versini, Antoine,Khene, Nadjib,Gaillet, Christine,Ca?eque, Tatiana,Müller, Sebastian,Rodriguez, Rapha?l
supporting information, p. 7369 - 7373 (2020/06/02)
Cancer stem cells (CSC) constitute a cell subpopulation in solid tumors that is responsible for resistance to conventional chemotherapy, metastasis and cancer relapse. The natural product Salinomycin can selectively target this cell niche by directly interacting with lysosomal iron, taking advantage of upregulated iron homeostasis in CSC. Here, inhibitors of the divalent metal transporter 1 (DMT1) have been identified that selectively target CSC by blocking lysosomal iron translocation. This leads to lysosomal iron accumulation, production of reactive oxygen species and cell death with features of ferroptosis. DMT1 inhibitors selectively target CSC in primary cancer cells and circulating tumor cells, demonstrating the physiological relevance of this strategy. Taken together, this opens up opportunities to tackle unmet needs in anti-cancer therapy.
Substituted phenyl pyrazolone derivatives and preparation and application (by machine translation)
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Paragraph 0034; 0037; 0038, (2019/01/08)
The present invention provides a substituted phenyl pyrazolone derivatives, in particular to a 2 - phenyl - pyrazoline - 3 - ketone compound and its pharmaceutically acceptable salt, solvate. The substituted acetic acid ethyl ester with sodium hydroxide in aqueous solution in the [...] reflux reaction, then in the palladium-carbon and hydrogen under the action of the hydrogenolysis benzyl, phenyl [...] obtained, with the bromochlorodifluoromethane alkane reaction to obtain the chloro, finally with the secondary amine on the condensation to obtain the target compound. The invention substituted phenyl pyrazoline compounds in vitro exhibits excellent capability of eliminating the free radicals, and have more strongly inhibit H3 receptor activity, exhibits excellent penetration of the blood brain barrier capacity, has a unique dual active, therefore, its for cerebral apoplexy, Alzheimer's disease, Parkinson's disease, progressive neurodegenerative diseases such as frozen sickness treatment has a unique clinical effect. The compound of the invention for treating central system system related disease and inflammatory disease application of the medicament. The formula structure is as follows: (by machine translation)
Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates
Li, Jiawen,Qian, Bo,Huang, Hanmin
, p. 7090 - 7094 (2018/11/23)
The first silver-catalyzed reaction of acetals or ketals with diazoesters leading to trisubstituted or tetrasubstituted β-alkoxyacrylates is now reported. A broad range of acetals and ketals bearing different substituents is compatible with this protocol and thus provides an attractive approach for the synthesis of complex β-alkoxyacrylates. The power of this method was further demonstrated by the successful synthesis of picoxystrobin, which is one of the most popular agricultural fungicides commercialized by Dupont.
Asymmetric Synthesis of Spiropyrazolones by Rhodium-Catalyzed C(sp2)?H Functionalization/Annulation Reactions
Zheng, Jun,Wang, Shao-Bo,Zheng, Chao,You, Shu-Li
supporting information, p. 4540 - 4544 (2017/04/11)
Rhodium-catalyzed C(sp2)?H functionalization reactions of 4-aryl-5-pyrazolones followed by [3+2] annulation reactions with alkynes provide rapid access to highly enantioenriched five-membered-ring 4-spiro-5-pyrazolones. The use of a chiral SCpRh catalyst enabled the synthesis of a large range of spiropyrazolones with all-carbon quaternary stereogenic centers in up to 99 % yield and 98 % ee from readily available substrates.
Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: An immediate access to diverse 3-aryl-4(1 H)-quinolones
Monastyrskyi, Andrii,Namelikonda, Niranjan K.,Manetsch, Roman
, p. 2513 - 2520 (2015/03/18)
A clean arylation protocol of ethyl acetoacetate was developed using hypervalent diaryliodonium salts under mild and metal-free conditions. The scope of the reaction, using symmetric and unsymmetric iodonium salts with varying sterics and electronics, was examined. Further, this method has been applied for the synthesis of antimalarial compound ELQ-300, which is currently in preclinical development.
Copper-catalyzed regio- and stereoselective O-arylation of enolates
Xu, Ze-Feng,Cai, Chen-Xin,Jiang, Min,Liu, Jin-Tao
, p. 3436 - 3439 (2014/07/21)
Copper-catalyzed O-arylation of enolates with diaryliodonium salts as arylating reagents was realized successfully. As important building blocks, β-aryloxy carbonyl compounds were obtained in up to 98% yield under mild conditions, and complete control of
Copper(I) enolate complexes in α-arylation reactions: Synthesis, reactivity, and mechanism
Huang, Zheng,Hartwig, John F.
supporting information; experimental part, p. 1028 - 1032 (2012/03/09)
Copper is all bound up: The copper-catalyzed α-arylation of carbonyl compounds occurs through oxidative addition of iodoarenes to the C-bound Cu I enolate species 1 to form an aryl-CuIII intermediate (see scheme). Computational results provide insight into the origins of the relative reactivity of various CuI enolate complexes in the reactions with iodoarenes. Copyright
Synthesis and biological evaluation of substituted pyrazoles as blockers of divalent metal transporter 1 (DMT1)
Cadieux, Jay A.,Zhang, Zaihui,Mattice, Maryanne,Brownlie-Cutts, Alison,Fu, Jianmin,Ratkay, Laszlo G.,Kwan, Rainbow,Thompson, Jay,Sanghara, Joseph,Zhong, Jing,Goldberg, Y. Paul
scheme or table, p. 90 - 95 (2012/02/16)
Three distinct series of substituted pyrazole blockers of divalent metal transporter 1 (DMT1) were elaborated from the high-throughput screening pyrazolone hit 1. Preliminary hit-to-lead efforts revealed a preference for electron-withdrawing substituents in the 4-amido-5-hydroxypyrazole series 6a-l. In turn, this preference was more pronounced in a series of 4-aryl-5- hydroxypyrazoles 8a-j. The representative analogs 6f and 12f were found to be efficacious in a rodent model of acute iron hyperabsorption. These three series represent promising starting points for lead optimization efforts aimed at the discovery of DMT1 blockers as iron overload therapeutics.
Pd-catalyzed coupling of β-hydroxy α-diazocarbonyl compounds with aryl iodides: A migratory insertion/β-hydroxy elimination sequence
Zhou, Lei,Liu, Yizhou,Zhang, Yan,Wang, Jianbo
supporting information; scheme or table, p. 3622 - 3624 (2011/05/02)
The coupling of β-hydroxy α-diazocarbonyl compounds with aryl halides is described, which proceeds through a Pd-catalyzed migratory insertion/β-OH elimination sequence. This reaction provides a new route to the synthesis of tetrasubstituted olefins.