22971-32-0Relevant articles and documents
Synthesis, structure-activity relationships, and antitumor studies of 2-benzoxazolyl hydrazones derived from alpha-(N)-acyl heteroaromatics
Easmon, Johnny,Pürstinger, Gerhard,Thies, Katrin-Sofia,Heinisch, Gottfried,Hofmann, Johann
, p. 6343 - 6350 (2006)
Recently we have described the antitumor activities of 2- benzoxazolylhydrazones derived from 2-formyl and 2-acetylpyridines. In search of a more efficacious analogue, compounds in which the 2-acetylpyridine moiety has been replaced by 2-acylpyridine and α-(N)-acetyldiazine/quinoline groups have been synthesized. The 2-acylpyridyl hydrazones inhibited in vitro cell proliferation in the nM range, whereas the hydrazones derived from the α-(N)-acetyldiazines/quinolines inhibited cell growth in the μM range. Compounds tested in the NCI-60 cell assay were effective inhibitors of leukemia, colon, and ovarian cancer cells. E-13k [N-benzoxazol-2-yl-N′-(1- isoquinolin-3-yl-ethylidene)-hydrazine] inhibited the proliferation of MCF-7 breast carcinoma cells more efficiently than nontransformed MCF-10A cells. It is not transported by P-glycoprotein and a weak MRP substrate. Increased concentrations of serum or α1-acid glycoprotein did not reduce the antiproliferative activity of the compound. In the in vivo hollow fiber assay, E-13k achieved a score of 24, with a net cell kill of OVCAR-3 (ovarian) and SF2-95 (CNS) tumor cells.
Catalytic α-Deracemization of Ketones Enabled by Photoredox Deprotonation and Enantioselective Protonation
Zhang, Chenhao,Gao, Anthony Z.,Nie, Xin,Ye, Chen-Xi,Ivlev, Sergei I.,Chen, Shuming,Meggers, Eric
supporting information, p. 13393 - 13400 (2021/09/03)
This study reports the catalytic deracemization of ketones bearing stereocenters in the α-position in a single reaction via deprotonation, followed by enantioselective protonation. The principle of microscopic reversibility, which has previously rendered this strategy elusive, is overcome by a photoredox deprotonation through single electron transfer and subsequent hydrogen atom transfer (HAT). Specifically, the irradiation of racemic pyridylketones in the presence of a single photocatalyst and a tertiary amine provides nonracemic carbonyl compounds with up to 97% enantiomeric excess. The photocatalyst harvests the visible light, induces the redox process, and is responsible for the asymmetric induction, while the amine serves as a single electron donor, HAT reagent, and proton source. This conceptually simple light-driven strategy of coupling a photoredox deprotonation with a stereocontrolled protonation, in conjunction with an enrichment process, serves as a blueprint for other deracemizations of ubiquitous carbonyl compounds.
Site-Selective Pd-Catalyzed C(sp3)?H Arylation of Heteroaromatic Ketones
Kudashev, Anton,Baudoin, Olivier
supporting information, p. 17688 - 17694 (2021/11/16)
A ligand-controlled site-selective C(sp3)?H arylation of heteroaromatic ketones has been developed using Pd catalysis. The reaction occurred selectively at the α- or β-position of the ketone side-chain. The switch from α- to β-arylation was realized by addition of a pyridone ligand. The α-arylation process showed broad scope and high site- and chemoselectivity, whereas the β-arylation was more limited. Mechanistic investigations suggested that α-arylation occurs through C?H activation/oxidative addition/reductive elimination whereas β-arylation involves desaturation and aryl insertion.
Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents
Wu, Qingsong,Han, Shuaijun,Ren, Xiaoxiao,Lu, Hongtao,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information, p. 6345 - 6348 (2018/10/20)
The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an alkylation reagent to form the structurally versatile alkylated (iso)quinolines and arenes. The method affords a convenient pathway for the introduction of alkyl groups into organic molecules.
Engineering an iridium-containing metal-organic molecular capsule for induced-fit geometrical conversion and dual catalysis
Li, Xuezhao,Wu, Jinguo,Chen, Liyong,Zhong, Xiaoming,He, Cheng,Zhang, Rong,Duan, Chunying
supporting information, p. 9628 - 9631 (2016/08/04)
By introducing photoactive fac-tris(2-phenylpyridine)iridium moieties as a ligand backbone to constrain the coordination geometry of cobalt ions, a multifunctional Ir2Co3-type capsule was achieved and showed induced-fit capsule-capsule conversion by cooperative binding one carbonate anion with the equatorial Co(ii) centers. The capsule combined photocatalysis and transition metal activation synergistically and exhibited efficient catalytic ability on visible light-activated α-trichloromethylation.
SUBSTITUTED AMINOTHIAZOLES AS INHIBITORS OF CANCERS, INCLUDING HEPATOCELLULAR CARCINOMA, AND AS INHIBITORS OF HEPATITIS VIRUS REPLICATION
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Paragraph 0140; 0141; 0150; 0151, (2013/04/24)
Pharmaceutical compositions of the invention are presented which comprise substiuted aminothiazoles derivatives. The substiuted aminothiazoles derivatives have a disease-modifying action in the treatment of diseases associated with unregulated cell growth. Such diseases include cancers such as hepatocellular carcinoma, and viral infections from a hepatitis virus.
Solubility and transfer processes of some hydrazones in biologically relevant solvents
Perlovich, German L.,Kazachenko, Vladimir P.,Strakhova, Nadezda N.,Schaper, Klaus-J.,Raevsky, Oleg A.
, p. 2659 - 2667 (2013/09/24)
Solubility values of 20 hydrazones in water, 1-octanol and hexane were determined by the isothermal saturation method. Thermophysical characteristics of fusion processes (melting points and fusion enthalpies) of the selected substances were measured by DS
THIAZOLYL COMPOUNDS USEFUL AS KINASE INHIBITORS
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Page/Page column 23, (2010/03/31)
The invention provides compounds of formula I [INSERT CHEMICAL STRUCTURE HERE] (I) and pharmaceutically acceptable salts thereof. The formula I thiazolyl compounds inhibit tyrosine kinase activity thereby making them useful as anticancer agents and for the treatment of Alzheimer's Disease.
A new and highly efficient water-soluble copper complex for the oxidation of secondary 1-heteroaryl alcohols by tert-butyl hydroperoxide
Boudreau, Josée,Doucette, Mike,Ajjou, Abdelaziz Nait
, p. 1695 - 1698 (2007/10/03)
The water-soluble copper complex generated in situ from CuCl2 and 2,2′-biquinoline-4,4′-dicarboxylic acid dipotassium salt (BQC), has been revealed as a highly efficient and selective catalyst for the oxidation of secondary 1-heteroaryl alcohols to the corresponding heteroaromatic ketones with aqueous tert-butyl hydroperoxide, under mild conditions. The catalytic system is compatible with different heterocycles such as pyridines, pyrroles, indoles, thiophens, furans, thiazoles, and imidazoles.
Mesoions and ketene valence isomers. Pyrrolo[1,2-a]pyridinylium olates and (2-pyridyl)carbonylketenes
Ye, Xuan,Andraos, John,Bibas, Herve,Wong, Ming Wah,Wentrup, Curt
, p. 401 - 406 (2007/10/03)
The synthesis and isolation of the pyrrolopyridinium olate system was discussed. The zwitterionic compounds were obtained by flash vacuum thermolysis (FVT) of picolinoylacetates. Nucleophilic addition reactions of zwitterionic compounds occurred by C-N bond cleavage to afford pyridine derivatives. The kinetic monitoring of such reactions revealed that they have extremely low activation enthalpies and very large negative activation entropies.
