26454-79-5

Usage

Malononitrile derivative

The compound is based on the malononitrile structure, which is a core structure found in many organic compounds.

Phenyl group substituted with a methoxy group

The phenyl group in the compound is substituted with a methoxy group (-OCH3), which can affect the compound's reactivity and properties.

White crystalline powder

The compound has a solid-state form that is white and crystalline, which can affect its solubility and other physical properties.

Molecular weight

255.27 g/mol The molecular weight of the compound, which is the mass of one mole of the compound, can be used to calculate various physical and chemical properties.

Used in organic synthesis

The compound is commonly used as a building block for the construction of more complex molecules in organic synthesis.

Potential applications in pharmaceutical and agrochemical industries

The compound has potential uses in the development of new drugs and agrochemicals due to its versatile reactivity and ability to participate in a variety of chemical reactions.

May have biological activities

The compound may have biological activities that make it of interest for medicinal chemistry research, potentially leading to the development of new drugs or therapies.

Upstream product

• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 109-77-3 malononitrile 

Downstream Products

• 1240949-46-5 5-(4-methoxyphenyl)-1H-pyrrole-3-carbonitrile 
• 374798-47-7 5-amino-3-(4-methoxybenzoyl)-1-phenyl-1H-pyrazole-4-carbonitrile 
• 26454-83-1 2-amino-5-(4-methoxyphenyl)-furan-3-carbonitrile 

Relevant academic research and scientific papers

Copper-Catalyzed Tandem Dehydrocyanation and [3+2] Cyclo-addition Reactions of Phenacylmalononitriles: Regioselective Synthesis of Functionalized 4-Benzoyl-5-cyanopyrazoles under Mild Conditions

A novel copper-catalyzed [3+2] cycloaddition reaction with concomitant in situ generation of benzoylacrylonitriles and nitrile imines from phenacylmalononitriles and hydrazonoyl chlorides, respectively, is reported. The reaction was performed using copper(I) chloride as catalyst and N-methylimidazole as a clean complexing agent/weak base to afford the functionalized 4-benzoyl-5-cyanopyrazoles in moderate to good yields and excellent regioselectivity under ambient conditions. This method provides rapid access to a wide range of highly functionalized 4-benzoyl-5-cyanopyrazoles.

Visible-light-accelerated pd-catalyzed cascade addition/ cyclization of arylboronic acids to γ- And β-ketodinitriles for the construction of 3-cyanopyridines and 3-cyanopyrrole analogues

The one-pot synthetic strategies for 2,4,6-triarylnicotinonitriles and 2,5-diaryl-1H-pyrrole-3-carbonitriles have been accomplished via a Pd-catalyzed coupling of arylboronic acid with 2-(3-oxo-1,3-diarylpropyl)malononitrile and 2-(2-oxo-2- arylethyl)malo

One-Step, Effective, and Cascade Syntheses of Highly Functionalized Cyclopentenes with High Diastereoselectivity

Tetrabutylammonium fluoride works as an effective organocatalyst for the cycloaddition between phenacylmalononitriles and electron-deficient olefins (having substituent groups of NO2, CHO, and COR), providing a facile synthetic route to versatile multifunctionalized cyclopentenes having an allylic quaternary carbon center bearing both cyano and carboxamide groups with high yields and high diastereoselectivity. Preliminary studies reveal that these functionalized cyclopentenes are convenient precursors for making α-cyano-functionalized cyclopentadienone oximes.

Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors

Epidermal growth factor receptor inhibitors are of importance in cancer therapy and possibly in the management of pain. Herein, we report a structure-activity relationship study with 29 new 6-aryl-furo[2,3-d]pyrimidin-4-amines, involving modification of the 4-amino group and 6-aryl function. The EGFR activity was especially dependent on having a chiral 4-benzylamino group with correct stereochemistry. Molecular dynamics indicate this to be due to favourable cation-π interactions. The most active inhibitor identified, equipotent to Erlotinib, was substituted with (R)-1-phenylethylamine at C-4 and a N1, N1-dimethyl-1,2-diamine group in para position of the 6-aryl moiety. These new furopyrimidines had a different off-target kinase profile when compared to Erlotinib, and also possessed high activity towards Ba/F3 EGFRL858R reporter cells. Further, comparing the EGFR data of the furo[2,3-d]pyrimidin-4-amines with that of the corresponding thieno- and pyrrolopyrimidines concludes the furopyrimidine scaffold to be highly useful for development of new epidermal growth factor receptor antagonists.

Phenacyl bromides revisited: Facile synthesis of some new pyrazoles, pyridazines, and their fused derivatives

Phenacylmalononitriles 8a, 8b react with hydrazines under dry conditions to afford the pyrazole derivatives 9a, 9b, 9c, 9d and in refluxing dioxane to afford the pyrazolo[3,4-c]pyridazine derivatives 11a, 11b, 11c, 11d and the pyridazine-6-imine derivativ

A highly diastereoselective five-component synthesis of 1-(alkylimino)-5,5-dicyano-3a-aryloctahydro-3-oxacyclobuta[cd]pentalene-1a,2,5a,5b(2H,3aH)-tetracarboxylates

A novel one-pot, five-component synthesis of 1-(alkylimino)-5,5-dicyano-3a-aryloctahydro-3-oxacyclobuta[cd]pentalene-1a,2,5a,5b(2H,3aH)-tetracarboxylates is described. A mixture of phenacyl bromide, malononitrile, isocyanide, and two equivalents of a dial

Novel 4-amino-furo[2,3-d]pyrimidines as Tie-2 and VEGFR2 dual inhibitors

A novel class of furo[2,3-d]pyrimidines has been discovered as potent dual inhibitors of Tie-2 and VEGFR2 receptor tyrosine kinases (TK) and a diarylurea moiety at 5-position shows remarkably enhanced activity against both enzymes. One of the most active compounds, 4-amino-3-(4-((2-fluoro-5-(trifluoromethyl) phenyl)amino-carbonylamino)phenyl)-2-(4-methoxyphenyl)furo[2,3-d]pyrimidine (7k) is 3 nM on both TK receptors and the activity is rationalized based on the X-ray crystal structure.

NOVEL CHEMICAL COMPOUNDS

The present invention relates generally to inhibitors of the kinases, such as GSK-3, and more particularly to fused pyrimidine compounds.

Synthesis of New Pyrrolo[2, 3-b]pyridines as a Potent Inhibitor of Tumour Necrosis Factor Alpha

The MAP kinase p38 plays a key role in the biosynthesis of the inflammatory cytokines tumor necrosis factor α (TNF-α) and 1L-1β. Accordingly, new pyrrolo[2,3]pyridine derivatives 5 a-d were prepared from 2-amino-3-cyanopyrroles 3 a-d via the intermediate

4-Acylamino-6-arylfuro[2,3-d]pyrimidines: Potent and selective glycogen synthase kinase-3 inhibitors

Modeling studies of a furo[2,3-d]pyrimidine GSK-3 hit compound 1 superimposed onto the X-ray crystal structure of a legacy pyrazolo[3,4-c] pyridazine GSK-3 inhibitor 2 led to the identification of 4-acylamino-6- arylfuro[2,3-d]pyrimidine template 3. Synth