94853-74-4

Usage

Uses

Used in Textile Industry:
(AZA((4-FLUOROPHENYL)AMINO)METHYLENE)METHANE-1,1-DICARBONITRILE is used as a dye for imparting vibrant yellow color to fabrics, contributing to the aesthetic appeal and visual variety of textile products.
Used in Plastics Industry:
In the plastics industry, (AZA((4-FLUOROPHENYL)AMINO)METHYLENE)METHANE-1,1-DICARBONITRILE is used as a pigment to enhance the color and appearance of various plastic materials, improving their marketability and consumer appeal.
Used in Pharmaceutical Industry:
(AZA((4-FLUOROPHENYL)AMINO)METHYLENE)METHANE-1,1-DICARBONITRILE is used as a pharmaceutical intermediate, playing a crucial role in the synthesis of new drugs and therapies. Its potential pharmacological properties are being studied to develop innovative treatments for various medical conditions.
Used in Chemical Research:
(AZA((4-FLUOROPHENYL)AMINO)METHYLENE)METHANE-1,1-DICARBONITRILE is also utilized in chemical research for understanding the properties and behavior of azo compounds, which can lead to the discovery of new applications and advancements in related fields.

Upstream product

• 371-40-4 4-fluoroaniline 
• 109-77-3 malononitrile 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 

Downstream Products

• 1173187-55-7 C₃₁H₂₁FN₈O₂S 
• 402502-36-7 C₉H₉FN₆ 

Relevant academic research and scientific papers

Synthesis of 2-arylamino-3-cyanoquinolines: Via a cascade reaction through a nitrilium intermediate

A new method for the preparation of 2-amino-3-cyanoquinolines from readily available aryldiazonium salts, 2-aminoarylketones, and malononitrile via a cascade reaction is reported. This one-pot approach involves the in situ generation of an N-arylnitrilium intermediate from the direct reaction of aryldiazonium salts and malononitrile, which undergoes intermolecular amination, Knoevenagel condensation, and then aromatization to yield the desired compound in moderate to good yields. This methodology features a quick assembly of C2 and C3 functionalized quinolines.

COMPOUNDS HAVING PSEUDOMONAS ANTI-BIOFILM PROPERTIES

The present invention relates to c-di-GMP lowering chemical compounds having anti- biofilm properties. In particular, the present invention relates to anti-biofilm compounds or salts or tautomers thereof for use in treatment and/or prevention of bacterial biofilm infection in human subjects caused by biofilm-forming bacteria of the genus Pseudomonas, in particular Pseudomonas spp. including P. aeruginosa. Methods of treating such infections in human subjects are contemplated as well. The present inventions further relates to the use of an anti-biofilm compound or a salt or tautomer thereof for dispersing biofilms in industrial water systems.

SAR study of 4-arylazo-3,5-diamino-1: H -pyrazoles: identification of small molecules that induce dispersal of Pseudomonas aeruginosa biofilms

By screening of a collection of 50 000 small-molecule compounds, we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of anti-biofilm agents. Here, we report a SAR study based on 60 analogues by examining ways in which the pharmacoph

Discovery, SAR study and ADME properties of methyl 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate as an HIV-1 replication inhibitor

Inspired by the antiviral activity of known pyrazole-based HIV inhibitors, we screened our in-house library of pyrazole-based compounds to evaluate theirin celluloactivity against HIV-1 replication. Two hits with very similar structures appeared from single and multiple-round infection assays to be non-toxic and active in a dose-dependent manner. Chemical expansion of their series allowed an in-depth and consistent structure-activity-relationship study (SAR) to be built. Further ADME evaluation led to the selection of 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate with an advantageous pharmacokinetic profile. Finally, examination of its mode of action revealed that this compound does not belong to the three main classes of anti-HIV drugs, a feature of prime interest in the context of viral resistance.

Computer-aided molecular design of pyrazolotriazines targeting glycogen synthase kinase 3

Numerous studies have highlighted the implications of the glycogen synthase kinase 3 (GSK-3) in several processes associated with Alzheimer’s disease (AD). Therefore, GSK-3 has become a crucial therapeutic target for the treatment of this neurodegenerative disorder. Hereby, we report the design and multistep synthesis of ethyl 4-oxo-pyrazolo[4,3-d][1–3]triazine-7-carboxylates and their biological evaluation as GSK-3 inhibitors. Molecular modelling studies allow us to develop this new scaffold optimising the chemical structure. Potential binding mode determination in the enzyme and the analysis of the key features in the catalytic site are also described. Furthermore, the ability of pyrazolotriazinones to cross the blood–brain barrier (BBB) was evaluated by passive diffusion and those who showed great GSK-3 inhibition and permeation to the central nervous system (CNS) showed neuroprotective properties against tau hyperphosphorylation in a cell-based model. These new brain permeable pyrazolotriazinones may be used for key in vivo studies and may be considered as new leads for further optimisation for the treatment of AD.

Synthesis, in vitro antimicrobial and cytotoxic activities of some new pyrazolo[1,5-a]pyrimidine derivatives

A new series of pyrazole 4–7 and pyrazolo[1,5-a]pyrimidine 8–13 were synthesized by using a simple, efficient procedure, and screened for their in-vitro antimicrobial and antitumor activities. Symmetrical and asymmetrical 3,6-diarylazo-2,5,7-triaminopyraz

Facile synthesis of 3,5-diaminopyrazole derivatives from nitrile intermediates

A novel series of 3,5-diaminopyrazole derivatives (2a-n) was achieved by the reaction of [2-(4-substitutedphenyl) hydrazinylidene] nitrile (1) with various substituted benz hydrazides. The synthesized compounds were characterized by 1H NMR, IR, mass spectroscopy and elemental analyses. The antioxidant potency of the compounds was tested keeping BHA as standard. Compounds 2a, 2b and 2c showed excellent antioxidant property comparable with the standard employed.

Multistep flow synthesis of 5-amino-2-aryl-2h-[1,2,3]-triazole-4-carbonitriles

1,2,3-Triazole has become one of the most important heterocycles in contemporary medicinal chemistry. The development of the copper-catalyzed Huisgen cycloaddition has allowed the efficient synthesis of 1-substituted 1,2,3-triazoles. However, only a few methods are available for the selective preparation of 2-substituted 1,2,3-triazole isomers. In this context, we decided to develop an efficient flow synthesis for the preparation of various 2-aryl-1,2,3-triazoles. Our strategy involves a three-step synthesis under continuous-flow conditions that starts from the diazotization of anilines and subsequent reaction with malononitrile, followed by nucleophilic addition of amines, and finally employs a catalytic copper(II) cyclization. Potential safety hazards associated with the formation of reactive diazonium species have been addressed by inline quenching. The use of flow equipment allows reliable scale up processes with precise control of the reaction conditions. Synthesis of 2-substituted 1,2,3-triazoles has been achieved in good yields with excellent selectivities, thus providing a wide range of 1,2,3-triazoles.

Mechanically activated solid-state synthesis of phenylhydrazone derivatives via high-speed ball milling

A series of phenylhydrazone derivatives was synthesized from arenediazonium tetrafluoroborates and active methylene compounds under high-speed ball milling. The reaction occurred in the absence of the solvent and products were obtained in good yield within short reaction times (no more than 30 min).