14476-72-3

Usage

Uses

Used in Organic Synthesis:
2-(2-oxo-2-phenylethyl)malononitrile is utilized as a reagent in organic synthesis for its unique structural properties, which can contribute to the formation of complex organic molecules. Its role in synthesis is valuable for the development of new chemical entities.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2-(2-oxo-2-phenylethyl)malononitrile is used as a precursor in the synthesis of potential drug candidates. Its specific structural features may offer advantages in the design of new therapeutic agents, although the development and use of such pharmaceuticals must carefully consider the compound's inherent toxicity.
Used in Material Science:
2-(2-oxo-2-phenylethyl)malononitrile is also considered for its potential applications in material science, where it may contribute to the development of new materials with unique properties. 2-(2-oxo-2-phenylethyl)malononitrile's structural elements could be leveraged to create materials with specific characteristics for various applications.

InChI:InChI=1/C11H8N2O/c12-7-9(8-13)6-11(14)10-4-2-1-3-5-10/h1-5,9H,6H2

Upstream product

• 105-36-2 ethyl bromoacetate 
• 109-77-3 malononitrile 
• 70-11-1 α-bromoacetophenone 
• 4341-85-9 malonitrile 

Downstream Products

• 93764-95-5 5-Amino-3-benzoyl-1-phenyl-1H-pyrazole-4-carbonitrile 
• 125041-27-2 5-Amino-3-benzoyl-1-p-tolyl-1H-pyrazole-4-carbonitrile 
• 125041-28-3 5-Amino-3-benzoyl-1-(4-chloro-phenyl)-1H-pyrazole-4-carbonitrile 
• 22109-04-2 2-amino-4,5-dihydro-5-phenyl-3-furancarbonitrile 
• 105576-67-8 3,5-Diamino-4-phenacylpyrazole 
• 14742-32-6 2-amino-5-phenylfuran-3-carbonitrile 
• 158692-52-5 2-chloro-3-cyano-5-phenylpyrrole 
• 144294-74-6 C₂₂H₁₄N₄S₂ 
• 122238-01-1 2-Amino-5-phenyl-1-p-tolyl-1H-pyrrole-3-carbonitrile 
• 122238-02-2 2-Amino-1-(4-chloro-phenyl)-5-phenyl-1H-pyrrole-3-carbonitrile 
• 122238-08-8 2-Amino-1-(4-nitro-phenyl)-5-phenyl-1H-pyrrole-3-carbonitrile 
• 210347-38-9 3-oxo-6-phenyl-2,3,4,5-tetrahydropyridazine-4-carbonitrile 
• 257871-12-8 thiophenacylmalononitrile 
• 18031-97-5 4-amino-6-phenylfuro[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Synthesis of functionalized cyclopentenes through allenic ketone-based multicomponent reactions

A novel and efficient synthesis of diversely functionalized cyclopentene derivatives through the multicomponent reactions of 1,2-allenic ketones with 4-chloroacetoacetate and malononitrile/cyanoacetate under mild and metal-free conditions is presented. Me

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.

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

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

Utility of pyrrole-2-thioacetohydrazide in synthesis of new heterocyclic compounds with promising antimicrobial activities and molecular docking studies

One-pot synthetic method for [(3-cyano-5-phenyl-1H-pyrrol-2-yl)sulfanyl]acetic acids 3a,b with excellent yield have been accomplished via a tetrabutylammonium bromide (TBAB) catalyzed reaction of mercaptoacetic acid with 2-(2-oxo-2-arylethyl) malononitrile under phase transfer catalysis conditions (PTC). The coupling of methyl [(3-cyano-5-phenyl-1H-pyrrol-2-yl)sulfanyl] acetate 4a,b with hydrazine gave the corresponding 2-[(3-cyano-5-aryl-1H-pyrrol-2yl)thio] acetohydrazides 5a,b, which reacted with glucose, acetylacetone, carbon disulfide, phenyl isothiocyanate, chloroacetyl chloride or benzaldehyde, to afford the compounds 6a,b–11a,b, respectively ranged from satisfactory to excellent yields. In vitro antibacterial and antifungal activities were assessed with good results. Furthermore, molecular docking experiments were done for the most active compounds against the E. coli MurB enzyme in order to determine the mechanism of their antibacterial activity and showed good binding interactions.

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.

PYRROLO AND PYRAZOLOPYRIMIDINES AS UBIQUITIN-SPECIFIC PROTEASE 7 INHIBITORS

The invention relates to inhibitors of USP7 inhibitors useful in the treatment of cancers, neurodegenerative diseases, immunological disorders, inflammatory disorders, cardiovascular diseases, ischemic diseases, viral infections and diseases, and bacterial infections and diseases, having the Formula: where m, n, X1, X2, R1-R5, R5′ and R6 are described herein.

Regioselective alkylation of isopropylidene- and cyclohexylidenepropanedinitrile with phenacyl bromides

Alkylation of isopropylidene- and cyclohexylidenepropanedinitrile with phenacyl bromides gave 2,2-bis(2-aryl-2-oxoethyl)propanedinitriles. Direct alkylation of propanedinitrile with phenacyl bromides afforded only 2-(2-aryl-2-oxoethyl)propanedinitriles.

Synthesis and docking studies of novel antitumor benzimidazoles

In this work, the benzimidazole-pyrrole conjugates 6a-h and benzimidazole-tetracycles conjugates 12-14 were prepared. The cytotoxicity of the compounds 3, 4a-h, 6a-h, 8, 10 and 12-14 was tested against lung cancer cell line A549. Compound 6b exhibited higher activity than the bis-benzoxazole natural product (UK-1), the standard. The tested 4g,h, 6a-h, 10 and 12-14 exhibited remarkable cytotoxicity activity against breast cancer cell line MCF-7 with higher activity than tamoxifen. Furthermore, compound 4h was found to be also more potent than doxurubicin. The antitumor promotion activity of synthesized compounds 4g,h, 6a-h, 10 and 12-14 has been estimated by studying their possible inhibitory effects on EBV-EA activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). Among the studied compounds, the inhibitory activities of compounds 8, 13 and 14 demonstrated strong inhibitory effects on the Epstein-Barr virus early antigen (EBV-EA) activation without showing any cytotoxicity on the Raji cells and their effects being stronger than that of a representative control, oleanolic acid. Moreover, the molecular docking of the new compounds into plasminogen activator (uPA) receptor has been in correlation with the antitumor activity. All synthesized compounds 3, 4a-h, 6a-h, 8, 10 and 12-14 were docked into same groove of the binding site of the native co-crystalized (4-iodobenzo[b]thiophene-2-carboxamidine) ligand (PDB code:1c5x) for activity explaination. Compounds 4h, 6b and 13, giving the best docking results, were further studied to estimate their effect on the level of uPA using AssayMax human urokinase (uPA) ELISA kit. In case of A549 cell line, compound 6 exhibited similar activity to MMC, and for MCF-7 cell line, compound 4h exhibited similar activity to doxorubicin, in inhibiting the expression of uPA.