59066-79-4

Upstream product

• 3156-37-4 4-bromo-β-nitrostyrene 
• 75-52-5 nitromethane 
• 1122-91-4 4-bromo-benzaldehyde 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 817-87-8 ethyl azidocarbonate 
• 4648-54-8 trimethylsilylazide 

Relevant academic research and scientific papers

A flow strategy for the rapid, safe and scalable synthesis of N-H 1, 2, 3-triazoles via acetic acid mediated cycloaddition between nitroalkene and NaN3

The N-unsubstituted 4-aryl-1H-1,2,3-triazoles were synthesized via the acetic acid promoted cycloaddition between β-nitrostyrenes with sodium azide under transition-metal-free conditions in a continuous flow microreactor. The continuous-flow microreactor provided a safe environment for the dangerous reagents NaN3 and nitroalkene, and offered such a rapid procedure that the triazoles were formed in less than 4 min. In addition, the excess sodium azide was quenched by the by-product HNO2 in the presence of acetic acid. The scale-up experiment proved again that the yield did not drop in the flow reaction. Moreover, the synthesis of N-unsubstituted 1,2,3-triazole was also explored via a one pot reaction with aldehyde, nitromethane and sodium azide, and this reaction was monitored with an “in-tube retention time gradient” (IT-RTG) technology, which may be a novel application of the continuous-flow microreactor.

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.

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.

Catalyst and solvent free microwave-assisted synthesis of substituted 1,2,3-triazoles

We report a microwave-assisted catalyst and solvent free synthesis of 1,2,3-triazoles through the cycloaddition of trimethylsilylazide and acetylenes. Utilization of a thermally stable azide source, elimination of a metal catalyst, solvent or any additives, and a convenient isolation procedure result in an overall greener approach to access 1,2,3-triazoles on a practical scale with good to excellent yields (55-99%).

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