14150-95-9

Usage

Synthesis Reference(s)

Synthetic Communications, 7, p. 509, 1977 DOI: 10.1080/00397917709409270

InChI:InChI=1/C5H6N2O/c6-5-3-1-2-4-7(5)8/h1-4H,6H2

Upstream product

• 504-29-0 2-aminopyridine 
• 5231-96-9 N-(2-pyridyl)acetamide 
• 5255-67-4 ethyl 2-pyridinylcarbamate 
• 6994-14-5 2-Acetamino-pyridin-1-oxid 
• 6974-72-7 2-pyridinecarboxamide 1-oxide 

Downstream Products

• 1202-34-2 di(pyridin-2-yl)amine 
• 1205-41-0 2-(pyridin-2-ylamino)pyridine 1-oxide 
• 1448644-09-4 5,6-diphenyl-3-[(pyridin-2-yl)amino]-1,2,4-triazine 

Relevant academic research and scientific papers

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.

PLANT GROWTH INHIBITING AGENT, AND PLANT GROWTH INHIBITING METHOD USING SAME

An object of the present invention is to provide a novel plant growth inhibiting agent and a plant growth inhibiting method using the same. The plant growth inhibiting agent of the present invention comprises, as an active ingredient, a compound represent

New Selective Inhibitors of ERG Positive Prostate Cancer: ERGi-USU-6 Salt Derivatives

Prostate cancer is among the leading causes of cancer related death of men in the United States. The ERG gene fusion leading to overexpression of near full-length ERG transcript and protein represents most prevalent (50-65%) prostate cancer driver gene alterations. The ERG oncoprotein overexpression persists in approximately 35% of metastatic castration resistant prostate cancers. Due to the emergence of eventual refractoriness to second- and third-generation androgen axis-based inhibitors, there remains a pressing need to develop drugs targeting other validated prostate cancer drivers such as ERG. Here we report the new and more potent ERG inhibitor ERGi-USU-6 developed by structure-activity studies from the parental ERGi-USU. We have developed an improved procedure for the synthesis of ERGi-USU-6 and identified a salt formulation that further improves its activity in biological assays for selective targeting of ERG harboring prostate cancer cells.

ERG ONCOGENE INHIBITORS

The present disclosure relates generally to compounds suitable as ERG inhibitors, including compositions comprising such compounds, methods for their use in treating diseases associated with overexpression of wild type ERG protein, an altered ERG protein, ERG gene transcription or ERG mRNA translation, and methods of making such compounds.

Nanocomposite-based inorganic-organocatalyst Cu(II) complex and SiO2- and Fe3O4 nanoparticles as low-cost and efficient catalysts for aniline and 2-aminopyridine oxidation

Bis-imino Cu(II) complex (CuLAn2), in which the imine ligand (HLAn) acts as a bidentate chelating ligand, was synthesized. The catalytic potential of the inorganic-organocatalyst was studied homogeneously and heterogeneously in the oxidation of aniline and 2-aminopyridine by H2O2 or tBuOOH. Two heterogeneous inorganic-organocatalysts, CuLAn2@Fe3O4 and CuLAn2@SiO2@Fe3O4, were synthesized by the successful immobilization of CuLAn2 on the Fe3O4 surface and the composited Fe3O4 with SiO2, respectively. The heterogeneous structure of those inorganic-organocatalysts was confirmed using Fourier-transform infrared, scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, transmission electron microscopy, and magnetic properties. The adsorption–desorption isotherms revealed respectable adsorption parameters (SBET, Vp, and rp). All catalysts exhibited high potential in the oxidation of aniline (with phenylhydroxylamine as the main product) and good potential in the oxidation of 2-aminopyridine, in the first attempt (with 2-nitropyridine-N-oxide and 2-nitrosopyridine-N-oxide as main products), at room temperature. Acetonitrile was found to be the best solvent compared to ethanol, dimethyl sulfoxide, chloroform, and water. The homogeneous catalyst exhibited reusability for three times. The heterogeneous catalysts, CuLAn2@Fe3O4 and CuLAn2@SiO2@Fe3O4, were active for five and seven times, respectively. A mechanism was proposed within electron and oxygen transfer processes.

Palladium-Catalyzed Electrochemical C-H Bromination Using NH4Br as the Brominating Reagent

The palladium-catalyzed electrochemical C-H bromination of benzamide derivatives under divided cells is developed, in which NH4Br serves as a brominating reagent and electrolyte. The protocol avoids the use of chemical oxidants and provides an alternative method for the synthesis of aryl bromides.

Synthesis method of 2-amino-4-fluoropyridine

The invention discloses a synthesis method of 2-amino-4-fluoropyridine. The synthesis method comprises the following synthesis steps: 1, taking diaminopyridine as the raw material, carrying out oxidation reaction to prepare 2-aminopyridine N-oxide a; 2, subjecting the compound a to nitration reaction with mixed acid to obtain 2-amino-4-nitropyridine N-oxide b; 3, carrying out acylation reaction onthe compound b and an acylation reagent to obtain 2-acetamino-4-nitropyridine N-oxide c; 4, carrying out reduction reaction on the compound c to obtain 2-acetamino-4-aminopyridine d; 5, carrying outdiazo-reaction on the compound d and HBF4 to obtain diazonium fluoroborate e; and 6, carrying out Balz-Schiemann reaction on the compound e to introduce fluorine atoms and conducting hydrolysis deacetylation to obtain 2-amino 4-fluoropyridine. The method provided by the invention solves the problems of long synthesis route, complicated operation, serious pollution, high cost, low yield and the like in existing synthesis methods.

Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates

A new approach to hetaryl carbamates through a tandem condensation/rearrangement reaction of 2-aminohetarene N-oxides was developed. The developed reaction is suitable for both five- and six-membered heterocycles and proceeds through the condensation of 2

Catalyst-free and selective oxidation of pyridine derivatives and tertiary amines to corresponding N-oxides with 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane

The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields. Graphical abstract: The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields.

Discovery of New Potential Anti-Infective Compounds Based on Carbonic Anhydrase Inhibitors by Rational Target-Focused Repurposing Approaches

In academia, compound recycling represents an alternative drug discovery strategy to identify new pharmaceutical targets from a library of chemical compounds available in house. Herein we report the application of a rational target-based drug-repurposing approach to find diverse applications for our in-house collection of compounds. The carbonic anhydrase (CA, EC 4.2.1.1) metalloenzyme superfamily was identified as a potential target of our compounds. The combination of a thoroughly validated docking screening protocol, together with in vitro assays against various CA families and isoforms, allowed us to identify two unprecedented chemotypes as CA inhibitors. The identified compounds have the capacity to preferentially bind pathogenic (bacterial/protozoan) CAs over human isoforms and represent excellent hits for further optimization in hit-to-lead campaigns.