85106-72-5

Usage

Uses

Used in Pharmaceutical Industry:
[(4-methoxyphenyl)amino](methylsulfanyl)methylidenepropanedinitrile is used as a potential drug for cancer treatment due to its anti-tumor and anti-inflammatory properties. It has shown promise in targeting and reducing the growth of cancer cells, making it a valuable candidate for further research and development in the pharmaceutical industry.
Used in Antifungal Applications:
In the field of antifungal research, [(4-methoxyphenyl)amino](methylsulfanyl)methylidenepropanedinitrile is used as a potential antifungal agent. Its ability to inhibit fungal growth makes it a candidate for the development of new antifungal drugs to combat various fungal infections.
Used in Antibacterial Applications:
Similarly, in the antibacterial field, {[(4-methoxyphenyl)amino](methylsulfanyl)methylidene}propanedinitrile is used as a potential antibacterial agent. Its demonstrated antibacterial activities suggest that it could be a valuable addition to the arsenal of antibiotics, particularly in the face of increasing antibiotic resistance.
Used in Research and Development:
[(4-methoxyphenyl)amino](methylsulfanyl)methylidenepropanedinitrile is also used in research and development for its potential applications in various fields, including medicine, pharmaceuticals, and biotechnology. Its unique properties and potential for therapeutic use make it an interesting subject for further study and experimentation.

Upstream product

• 5147-80-8 [Bis(methylthio)methylene]malononitrile 
• 104-94-9 4-methoxy-aniline 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 
• 109-77-3 malononitrile 
• 74-88-4 methyl iodide 

Downstream Products

• 512845-61-3 1H-1-methyl-3-amino-4-cyano-5-(4-methoxyphenylamino)pyrazole 
• 900473-00-9 C₁₂H₁₂N₆O 
• 130224-50-9 4-amino-3-(p-methoxyphenylamino)pyrazolo<3,4-d>pyrimidine 
• 183738-77-4 4-(3-chloro-phenylamino)-3-(4-methoxy-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine 
• 512846-06-9 2-furan-2-yl-N₉-(4-methoxy-phenyl)-8-methyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5,9-diamine 
• 512845-94-2 3-amino-1H-1-methyl-5-(4-methoxyphenylamino)-4-[3-(2-furyl)-1,2,4-triazol-5-yl]pyrazole 
• 512845-82-8 8-methyl-2-(2-furyl)-9-(4-methoxyphenylamino)-pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine 
• 824398-27-8 C₁₅H₁₂ClN₅O 
• 824398-99-4 7-(2-amino-2-methylpropylamino)-2-(4-methoxyphenylamino)-5-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile 
• 824397-94-6 2-(4-methoxyphenylamino)-5-methyl-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile 

Relevant academic research and scientific papers

Triflic acid-mediated N-heteroannulation of β-anilino-β-(methylthio)acrylonitriles: a facile synthesis of 4-amino-2-(methylthio)quinolines

Various functionalised 4-amino-2-(methylthio)quinolines are synthesised through triflic acid-mediated N-heteroannulation of α-functionalized-β-anilino-β-(methylthio)acrylonitriles for the first time. The N-heteroannulation process is highly chemoselective and has mild reaction conditions. However, this process fails in the absence of the β-methylthio group in the acrylonitriles. In addition, a new double N-heteroannulation process is demonstrated to synthesise indolo[3,2-c]quinolines from non-heterocyclic precursors. Natural product isocryptolepine is synthesised in four steps from an acyclic precursor.

Pyrazolopyrimidines: Potent Inhibitors Targeting the Capsid of Rhino- and Enteroviruses

There are currently no drugs available for the treatment of enterovirus (EV)-induced acute and chronic diseases such as the common cold, meningitis, encephalitis, pneumonia, and myocarditis with or without consecutive dilated cardiomyopathy. Here, we report the discovery and characterization of pyrazolopyrimidines, a well-tolerated and potent class of novel EV inhibitors. The compounds inhibit the replication of a broad spectrum of EV in vitro with IC50 values between 0.04 and 0.64 μM for viruses resistant to pleconaril, a known capsid-binding inhibitor, without affecting cytochrome P450 enzyme activity. Using virological and genetics methods, the viral capsid was identified as the target of the most promising, orally bioavailable compound 3-(4-trifluoromethylphenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine (OBR-5-340). Its prophylactic as well as therapeutic application was proved for coxsackievirus B3-induced chronic myocarditis in mice. The favorable pharmacokinetic, toxicological, and pharmacodynamics profile in mice renders OBR-5-340 a highly promising drug candidate, and the regulatory nonclinical program is ongoing. Curing the common cold! A cluster of pyrazolopyrimidines with potent broad-spectrum activity against enteroviruses was discovered. Extensive structure-property relationship analyses led to the identification of 3-(4-trifluoromethyl-phenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine, shown to be a blocker of the viral capsid protein, as a lead compound for drug development with favorable physicochemical, pharmacokinetic, and toxicological properties.

A one-pot, three-component aminotriazine annulation onto 5-aminopyrazole-4-carbonitriles under microwave irradiation

A one-pot, three-component, microwave-assisted reaction of 5-aminopyrazole-4-carbonitriles, triethyl orthoformate and cyanamide afforded novel 7-arylamino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The reaction proceeded in a chemo- and regioselective manner resulting in the successful amino-1,3,5-triazine annulation onto 5-aminopyrazole-4-carbonitriles to give 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The operational simplicity of the method and high purity of the products, which can be isolated via simple filtration, make this approach attractive for the preparation of a library of compounds for drug discovery processes.

One-pot synthesis of 6-substituted amino-2,4-diaminopyrimidine derivatives using ketene dithioacetals with amines and guanidine carbonate

6-Substituted amino-2,4-diaminopyrimidine derivatives were prepared by one-pot synthesis using ketene dithioacetals, amine compounds, and guanidine carbonate in pyridine. These pyrimidine products displayed blue fluorescence in the solid state.

Discovery of novel 2-anilinopyrazolo[1,5-a]pyrimidine derivatives as c-Src kinase inhibitors for the treatment of acute ischemic stroke

We synthesized a series of novel 2-anilinopyrazolo[1,5-a]pyrimidine derivatives and evaluated their ability to inhibit c-Src kinase; 7-(2-amino-2-methylpropylamino)-5-cyclopropyl-2-(3,5-dimethoxyphenylamino) pyrazolo-[1,5-a]pyrimidine-3-carboxamide 7o and

PHARMACEUTICALLY ACTIVE COMPOUNDS HAVING A TRICYCLIC PYRAZOLOTRIAZOLOPYRIMIDINE RING STRUCTURE AND METHODS OF USE

New compounds having a tricyclic pyrazolotriazolopyrimidine ring structure are provided and methods of using those compounds for a variety of therapeutic indications.

Design, synthesis, and biological evaluation of C9- and C2-substituted pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as new A2A and A3 adenosine receptors antagonists

In the past few years, our group has been involved in the development of A2A and A3 adenosine receptor antagonists which led to the synthesis of SCH58261 (5-amino-7-(2-phenylethyl)-2-(2-furyl)pyrazolo[4,3-e]-1,2,4-triazolo [1,5-c]pyrimidine, 61), potent and very selective at the A2A receptor subtype, and N8-substituted-pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c] pyrimidines-N5-urea or amide (MRE series, b), very selective at the human A3 adenosine receptor subtype. We now describe a large series of C9- and C2-substituted pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines to represent an extension of structure-activity relationship work on this class of tricyclic compounds. The introduction of a substituent at 9 position of the tricyclic antagonistic structure led to retention of receptor affinity but a loss of selectivity in respect to the lead compounds b, N8-substituted-pirazolo[4,3-e]-1,2,4-triazolo[1,5-c] pyrimidines-N5-urea or -amide. The substitution of the furanyl moiety of compound 61, necessary for receptor binding, with a phenyl or a substituted aromatic ring (compounds 5a-d, 6-8), caused a complete loss of the affinity at all the adenosine receptor subtypes, demonstrating that the furanyl ring is a necessary structural element to guarantee interaction with the adenosine receptor surface. The introduction of an ethoxy group at the ortho position of the aromatic ring to mimic the oxygen of the furan (compound 5c, 5-amino-7-(2-phenylethyl)-2-(2-ethoxyphenyl)pyrazolo[4,3-e]-1,2, 4-triazolo[1,5-c]pyrimidine) did not enhance affinity. The introduction of the cycloaminomethyl function by Mannich reaction at the 5′ position of the furanyl ring of 61 and the C9-substituted compound 41 (5-amino-8-methyl-9-methylsulfanyl-2-(2-furyl)-pyrazolo[4,3-e]-1,2, 4-triazolo[1,5-c]pyrimidine) resulted in complete water solubility but a loss of receptor affinity. We can conclude that modifications or substitutions at the furanyl ring are not allowed and the introduction of a substituent at the 9-position of the core pyrazolo-triazolo-pyrimidine structure caused a severe loss of selectivity, probably due to an increased steric hindrance of the radical introduced.

Synthesis and antimalarial activity of substituted pyrazole derivatives

The development of new antimalarial drugs is an urgent priority considering the increasing prevalence of drug-resistant Plasmodium falciparum parasites. A series of pyrazoles are described as part of efforts directed toward the synthesis of some potent an

Use of a pharmacophore model for the design of EGF-R tyrosine kinase inhibitors: 4-(Phenylamino)pyrazolo[3,4-d]pyrimidines

In the course of the random screening of a pool of CIBA chemicals, the two pyrazolopyrimidines 1 and 2 have been identified as fairly potent inhibitors of the EGF-R tyrosine kinase. Using a pharmacophore model for ATP- competitive inhibitors interacting w