33263-03-5Relevant articles and documents
Triazole-Based Inhibitors of the Wnt/β-Catenin Signaling Pathway Improve Glucose and Lipid Metabolisms in Diet-Induced Obese Mice
Obianom, Obinna N.,Ai, Yong,Li, Yingjun,Yang, Wei,Guo, Dong,Yang, Hong,Sakamuru, Srilatha,Xia, Menghang,Xue, Fengtian,Shu, Yan
, p. 727 - 741 (2019/01/21)
Wnt/β-catenin signaling pathway is implicated in the etiology and progression of metabolic disorders. Although lines of genetic evidence suggest that blockage of this pathway yields favorable outcomes in treating such ailments, few inhibitors have been used to validate the promising genetic findings. Here, we synthesized and characterized a novel class of triazole-based Wnt/β-catenin signaling inhibitors and assessed their effects on energy metabolism. One of the top inhibitors, compound 3a, promoted Axin stabilization, which led to the proteasome degradation of β-catenin and subsequent inhibition of the Wnt/β-catenin signaling in cells. Treatment of hepatocytes and high fat diet-fed mice with compound 3a resulted in significantly decreased hepatic lipid accumulation. Moreover, compound 3a improved glucose tolerance of high fat diet-fed mice without noticeable toxicity, while downregulating the genes involved in the glucose and fatty acid anabolisms. The new inhibitors are expected to be further developed for the treatment of metabolic disorders.
Benzamide compound containing 1,2,3-triazole structure and application of benzamide compound
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, (2018/03/24)
The invention relates to benzamide derivatives containing a 1,2,3-triazole structure shown in a general formula I as well as pharmaceutically acceptable salts, hydrates or prodrugs thereof and a preparation method thereof. Substituent groups X, Ar, R1 and
Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones
Li, Ting,Chen, Minglu,Yang, Lei,Xiong, Zhengxin,Wang, Yongwei,Li, Fei,Chen, Dongyin
, p. 868 - 874 (2016/01/20)
An efficient and practical copper-catalyzed consecutive synthesis of quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones from easily available 2-halobenzamides (or 2-halonicotinamides), aldehydes, and sodium azide has been developed, which gave the corresponding target products in 50-95% yields for 29 examples. This remarkable consecutive process involved sequential copper-catalyzed SNAr, reduction, cyclization, and oxidation. Notably, this work would provide a novel synthetic strategy for bioactive molecules containing quinazolinone class skeletons.
Triplex-forming ability of oligonucleotides containing 1-aryl-1,2,3- triazole nucleobases linked via a two atom-length spacer
Hari, Yoshiyuki,Nakahara, Motoi,Obika, Satoshi
, p. 5583 - 5588 (2013/09/02)
Phosphoramidites containing 2-propynyloxy or 1-butyn-4-yl as nucleobase precursors were synthesized and introduced into oligonucleotides using an automated DNA synthesizer. Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of the oligonucleotides wi
Template synthesis of benzannulated N-heterocyclic carbene ligands
Hahn, F. Ekkehardt,Langenhahn, Volker,Meier, Nicole,Luegger, Thomas,Fehlhammer, Wolf Peter
, p. 704 - 712 (2007/10/03)
The reaction of 2-azidophenyl isocyanide (7) with [M(CO)5(thf)] (M = Cr, W) yields the isocyanide complexes [M(CO)5(7)] (M = Cr 8, M = W 9). Complexes 8 and 9 react with tertiary phosphines such as triphenylphosphane at the azido fun
A thiazine-S-oxide, Staudinger/aza-Wittig based synthesis of benzodiazepines and benzothiadiazepines
Anwar,Grimsey,Hemming,Krajniewski,Loukou
, p. 10107 - 10110 (2007/10/03)
A new approach to the synthesis of imine containing 1,2,5-benzothiadiazepine-1,1-dioxides and 1,4-benzodiazepin-5-ones using iminophosphoranyl thiazine-S-oxides as precursors is reported. Key steps include a Staudinger reaction, an aza-Wittig reaction and
Schmidt reaction of some constrained aromatic acids, and related topics
Ruediger, Edward H.,Gandhi, Sham S.,Gibson, Martin S.,Farcasiu, Dan,Uncuta, Cornelia
, p. 577 - 579 (2007/10/02)
Schmidt reaction of phthalic acid in 90-98percent sulfuric acid gives anthranilic acid and anthranilazide (major products) by a process considered to involve 3,1-benzoxazin-2,4(1H)-dione as intermediate.Benzimidazol-2-one is produced in this reaction by a secondary process from anthranilazide; it is also produced by photolysis of anthranilazide.Under Schmidt reaction conditions, 1,2,3-benzotriazin-4(3H)-one gives o-azidobenzamide.Under similar conditions, the lactol of 4-formyl-5-phenanthroic acid gives 1-azapyren-2(1H)-one and phenanthrene-4,5-dicarboximide, while phenanthrene-4,5-dicarboxylic acid gives 1-azapyren-2(1H)-one.Diphenic acid yields phenanthridone and 2,2'-diaminobiphenyl in proportions dependent on the sulfuric acid concentration.
Ring-expansion of Azidobenzenesulphonamides and Azidobenzamides
Brown, Thomas B.,Lowe, Philip R.,Schwalbe, Carl H.,Stevens, Malcolm F.G.
, p. 2485 - 2490 (2007/10/02)
4-Azidobenzenesulphonamides and 2- and 4-azidobenzamides undergo phototransformation to 2-alkoxy-3H-azepines in alcohols but the yields are low.Ring-expansion of 4-azidobenzenesulphonamide and 4-azidobenzenesulphonylguanidine in aqueous tetrahydrofuran to 3H-azepin-2(1H)-ones proceeds via a singlet nitrene pathway; thermolysis of 4-azidobenzenesulphonamide in aqueous dioxane gave only the triplet-derived product, sulphanilamide.Efficient de-azidation of 4-azidobenzesulphonamides and 4-azidobenzamides can be accomplished by heating the azides at 105 deg C in hydrazine hy drate.The crystallographic analysis of 5-sulphamoyl-3H-azepin-2(1H)-one shows the molecule to be non-planar with the azepine ring puckered in a boat form.The lactam configuration is confirmed with the carbonyl group having a bond length of 1.231 Angstroem.
