59066-80-7

Upstream product

• 768-60-5 4-methoxyphenylacetylen 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 1078739-24-8 4-(4-methoxyphenyl)-1-tosyl-1H-1,2,3-triazole 
• 817-87-8 ethyl azidocarbonate 

Downstream Products

• 1369584-15-5 4-(4-methoxyphenyl)-2-(1-(trimethylsilyl)-3-phenyl-3-p-tolylpropa-1,2-dienyl)-2H-1,2,3-triazole 
• 1369584-16-6 4-(4-methoxyphenyl)-1-(1-(trimethylsilyl)-3-phenyl-3-p-tolylpropa-1,2-dienyl)-1H-1,2,3-triazole 
• 1305196-73-9 2-(4-fluorophenyl)-4-(4-methoxyphenyl)-2H-1,2,3-triazole 

Relevant academic research and scientific papers

Cycloaddition of: N -sulfonyl and N -sulfamoyl azides with alkynes in aqueous media for the selective synthesis of 1,2,3-triazoles

The cycloaddition of N-sulfonyl and N-sulfamoyl azides with terminal alkynes generally produces amide derivatives via ketenimine intermediates. We herein delineate a Cu(i) catalyzed method using a prolinamide ligand that selectively generates N-sulfonyl a

A [3+2] cycloaddition-1,2-acyl migration-hydrolysis cascade for regioselective synthesis of 1,2,3-triazoles in water

A cascade sequence involving [3+2] cycloaddition, 1,2-acyl migration and hydrolysis produces 2H-1,2,3-triazolesviathe regioselective formation ofN2-carboxyalkylated triazoles. The reaction proceeds in aqueous media through intriguing reaction kinetics using a CuI-prolinamide catalyst system. Prolinamide promotes the novel organocatalytic 1,2-acyl migration as well as hydrolysis of the resultingN2-carboxyalkylated triazoles.

Synthesis and biological evaluation of selective survivin inhibitors derived from the MX-106 hydroxyquinoline scaffold

The survivin (BIRC5) expression is very low in normal differentiated adult tissues, but it is one of the most widely upregulated genes in tumor cells. The overexpression of survivin in many cancer types has been positively correlated with resistance to chemotherapy, tumor metastasis, and poor patient survival. Survivin is considered to be a cancer specific biomarker and serves as a potential cancer drug target. In this report, we describe the design and syntheses of a series of novel selective survivin inhibitors based on the hydroxyquinoline scaffold from our previously reported lead compound MX-106. The best compound identified in this study is compound 12b. In vitro, 12b inhibited cancer cell proliferation with an average IC50 value of 1.4 μM, using a panel of melanoma, breast, and ovarian cancer cell lines. The metabolic stability of 12b improved over MX-106 by 1.7-fold (88 vs 51 min in human microsomes). Western blot analyses demonstrated that treatments with 12b selectively decreased survivin protein levels, but negligibly affected other closely related members in the IAP family proteins, and strongly induced cancer cell apoptosis. In vivo, compound 12b effectively inhibited melanoma tumor growth when tested using a human A375 melanoma xenograft model. Further evaluation using an aggressive, orthotopic ovarian cancer mouse model showed that 12b was highly efficacious in suppressing both primary tumor growth in ovaries and tumor metastasis to multiple peritoneal organs. Collectively, results in this study strongly suggest that the hydroxyquinoline scaffold, represented by 12b and our earlier lead compound MX-106, has abilities to selectively target survivin and is promising for further preclinical development.

VASCULAR ADHESION PROTEIN-1 (VAP-1) MODULATORS AND THERAPEUTIC USES THEREOF

Disclosed herein are small molecule Vascular Adhesion Protein- 1 (VAP-1) modulator compositions, pharmaceutical compositions, the use and preparation thereof.

Green preparation method of 2H-1, 2, 3-triazole compound

The invention discloses a green preparation method of a 2H-1, 2, 3-triazole compound, which comprises the following steps of: by using 1, 2, 3-triazole derivative as a reaction raw material, copper sulfate as a catalyst and PEG400 as a reaction solvent, carrying out substitution reaction at 60 DEG C to obtain the target product 2H-1, 2, 3-triazole compound. According to the method, the target product 2H-1, 2, 3-triazole compound is finally prepared by taking cheap and easily available copper salt copper sulfate as a catalyst and taking PEG400 as a green reaction solvent, and the method has theadvantages of green and mild reaction conditions, cheap and easily available catalyst, simple operation, relatively high yield, wide reaction substrate universality and the like.

p-Toluenesulfonic acid-promoted autocatalytic hydrolyzation of 1-tosyl-1,2,3-triazoles

The first example of autocatalytic hydrolyzation of 4-aryl-1-tosyl-1,2,3-triazoles induced by p-toluenesulfonic acid was reported, providing an effective and metal-free synthetic approach to deliver a broad range of new 4-aryl-2H-1,2,3-triazoles in good yields. The kinetic profile of this hydrolyzation suggested that this reaction has exponential autocatalytic behavior.

A NH - 1, 2, 3 - triazole synthetic method

The invention discloses a method for synthesizing NH-1,2,3-triazole shown by a formula (I). Under the catalytic action of a Lewis acid catalyst, nitroalkene shown by a formula (II) and hydrazoic acid salt undergo 1,3-dipolar cycloaddition, wherein Ar is p

Reaction between Azidyl Radicals and Alkynes: A Straightforward Approach to NH-1,2,3-Triazoles

Reaction between nitrogen-centered radicals and unsaturated C-C bonds is an effective synthetic strategy for the construction of nitrogen-containing molecules. Although the reactions between nitrogen-centered radicals and alkenes have been studied extensively, their counterpart reactions with alkynes are extremely rare. Herein, the first example of reactions between azidyl radicals and alkynes is described. This reaction initiated an efficient cascade reaction involving inter-/intramolecular radical homolytic addition toward a C-C triple bond and a hydrogen-atom transfer step to offer a straightforward approach to NH-1,2,3-triazoles under mild reaction conditions. Both the internal and terminal alkynes work well for this transformation and some heterocyclic substituents on alkynes are compatible. This mechanistically distinct strategy overcomes the inherent limitations associated with azide anion chemistry and represents a rare example of reactions between a nitrogen-centered radicals and alkynes.