19212-27-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Oxo-4-phenylbutanenitrile is utilized as a key component in the development of pharmaceuticals due to its cytotoxic activities. It contributes to the therapeutic effects of the petroleum ether fruit extract of Brucea javanica fruits, which are recognized for their potential in treating various health conditions.
Used in Cancer Treatment Research:
In the field of cancer research, 3-Oxo-4-phenylbutanenitrile is used as a cytotoxic agent for its potential to inhibit the growth and proliferation of cancer cells. Its presence in the fruit extract of Brucea javanica suggests that it may play a role in the development of natural compounds for cancer treatment, offering an alternative or complementary approach to conventional therapies.

Upstream product

• 75-11-6 diiodomethane 
• 60299-77-6 cinnamoyl cyanide 
• 103-82-2 phenylacetic acid 
• 372-09-8 cyanoacetic acid 
• 103-80-0 phenylacetyl chloride 
• 101-97-3 Ethyl 2-phenylethanoate 
• 95092-10-7 N-methoxy-N-methyl-2-phenylacetamide 
• 75-05-8 acetonitrile 
• 1116-98-9 cyanoacetic acid tert-butyl ester 
• 100-44-7 benzyl chloride 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 101-41-7 benzeneacetic acid methyl ester 

Downstream Products

• 87942-97-0 4-Brom-3-oxo-4-phenylbutannitril 
• 2901-29-3 ethyl 2,4-diphenyl-3-oxobutanoate 
• 222056-50-0 5-benzyl-2-(2,2-diethoxy-ethyl)-2H-pyrazol-3-ylamine 
• 150712-24-6 3-benzyl-1H-pyrazol-5-amine 
• 347376-01-6 C₁₀H₁₅NO 
• 1159001-72-5 4-phenyl-3-(p-tolylamino)but-2-enenitrile 
• 59757-38-9 (E/Z)-2-((dimethylamino)methylene)-3-oxo-4-phenylbutanenitrile 
• 1047644-97-2 N-[3-amino-1-(phenylmethyl)propyl]-4-bromo-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride 
• 1047644-96-1 1,1-dimethylethyl [3-({[4-bromo-5-(1-methyl-1H-pyrazol-5-yl)-2-thienyl]carbonyl}amino)-4-phenylbutyl]carbamate 

Relevant academic research and scientific papers

A new β-keto amide synthesis

In a modification of the Wierenga-Skulnick β-ketoester synthesis, the dianions of malonic acid mono-amides were condensed with acid chlorides. Acidic workup led to decarboxylation and isolation of the corresponding β-keto amides in good-to-excellent yield

Solid-phase C-acylation of active methylene compounds

Active methylene compounds were attached to the Wang resin by an ester linkage. C-acylation was achieved with a reactive species generated in sire by the combination of a carboxylic acid, diethyl phosphorocyanidate, and triethylamine. Cleavage from the resin with simultaneous decarboxylation gave the products in moderate to good yield.

Identification of diphenylalkylisoxazol-5-amine scaffold as novel activator of cardiac myosin

To identify novel potent cardiac myosin activator, a series of diphenylalkylisoxazol-5-amine compounds 4–7 have been synthesized and evaluated for cardiac myosin ATPase activation. Among the 37 compounds, 4a (CMA at 10 μM = 81.6%), 4w (CMA at 10 μM = 71.2%) and 6b (CMA at 10 μM = 67.4%) showed potent cardiac myosin activation at a single concentration of 10 μM. These results suggested that the introduction of the amino-isoxazole ring as a bioisostere for urea group is acceptable for the cardiac myosin activation. Additional structure–activity relationship (SAR) studies were conducted. Para substitution (-Cl, –OCH3, -SO2N(CH3)2) to the phenyl rings or replacement of a phenyl ring with a heterocycle (pyridine, piperidine and tetrahydropyran) appeared to attenuate cardiac myosin activation at 10 μM. Additional hydrogen bonding acceptor next to the amino group of the isoxazoles did not enhance the activity. The potent isoxazole compounds showed selectivity for cardiac myosin activation over skeletal and smooth muscle myosin, and therefore these potent and selective isoxazole compounds could be considered as a new series of cardiac myosin ATPase activators for the treatment of systolic heart failure.

5- OR 7-AZAINDAZOLES AS BETA-LACTAMASE INHIBITORS

The present invention relates to β-lactamase inhibitors having the following general formula (I): wherein R1-R4 and X1-X2 are defined in the specification, pharmaceutical composition thereof, and use thereof for the treatment of a bacterial infection, alone or in combination with β-lactam antibiotics and/or other antibiotics and/or other β-lactamase inhibitors.

Electrophile-Directed Diastereoselective Oxonitrile Alkylations

Diastereoselective alkylation of prochiral oxonitrile dianions with secondary alkyl halides efficiently installs two contiguous stereogenic centers. The confluence of nucleophilic trajectory and the electrophile chirality causes distinct steric differences that allow efficient discrimination for one of the six possible conformers. Numerous oxonitrile-derived dianions efficiently displace secondary alkyl halides propagating the electrophile chirality to efficiently install two contiguous tertiary centers. The prevalence of chiral, secondary electrophiles makes the interdigitated alkylation of chiral electrophiles a particularly attractive route because the resulting oxonitriles are readily transformed into bioactive heterocycles.

Palladium-Catalyzed Carbonylative α-Arylation of tert -Butyl Cyanoacetate with (Hetero)aryl Bromides

A three-component coupling protocol has been developed for the generation of 3-oxo-3-(hetero)arylpropanenitriles via a carbonylative palladium-catalyzed α-arylation of tert-butyl 2-cyanoacetates with (hetero)aryl bromides followed by an acid-mediated decarboxylation step. Through the combination of only a stoichiometric loading of carbon monoxide and mild basic reaction conditions such as MgCl2 and dicyclohexylmethylamine for the deprotonation step, an excellent functional group tolerance was ensured for the methodology. Through the use of 13C-labeled carbon monoxide generated from 13COgen, the corresponding 13C-isotopically labeled β-ketonitriles were obtained, and these products could subsequently be converted into cyanoalkynes and 3-cyanobenzofurans with site specific 13C-isotope labeling. (Chemical Equation Presented).

SULFONYLAMINOPYRIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE

Provided are sulfonylaminopyridine compounds that are inhibitors of ITK kinase, compositions containing these compounds and methods for treating diseases mediated by ITK kinase. In particular, provided are compounds of Formula (I), (II) or (III), stereoisomers, tautomers, solvates, prodrugs or pharmaceutically acceptable salts thereof, where n, R1, R2, R3, R6 and R7 are defined herein, pharmaceutical compositions comprising the compound and a pharmaceutically acceptable carrier, adjuvant or vehicle, methods of using the compound or composition in therapy, for example, for treating a disease or condition mediated by ITK kinase in a patient.

Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides

A synthesis of β-oxonitriles is reported via the generation of R1R2CLiCN species followed by the trapping with variously decorated Weinreb amides. The optimization study revealed that lithiation of acetonitriles is best accomplished by deprotonation with MeLi-LiBr at low temperature. The protocol can be conveniently adapted to the synthesis of α-mono or α,α-disubstituted cyanoketones. 15N- and 17O-NMR data are reported for selected compounds. This journal is

Substituted pyrazoloquinazolinones and pyrroloquinazolinones as allosteric modulators of group II metabotropic glutamate receptors

The present invention relates to the pyrazoloquinazolinone and pyrroloquinazolinone derivatives of the general formula (I), as well as pharmaceutical compositions containing them, and their use in the treatment and/or prophylaxis of conditions associated with altered glutamatergic signalling and/or functions, and/or conditions which can be affected by alteration of glutamate level or signalling in mammals, in particular their use in the treatment and/or prophylaxis of acute and chronic neurological and/or psychiatric disorders.

SUBSTITUTED PYRAZOLOQUINAZOLINONES AND PYRROLOQUINAZOLINONES AS ALLOSTERIC MODULATORS OF GROUP II METABOTROPIC GLUTAMATE RECEPTORS

The present invention relates to the pyrazoloquinazolinone and pyrroloquinazolinone derivatives of the general formula (I), as well as pharmaceutical compositions containing them, and their use in the treatment and/or prophylaxis of conditions associated with altered glutamatergic signalling and/or functions, and/or conditions which can be affected by alteration of glutamate level or signalling in mammals, in particular their use in the treatment and/or prophylaxis of acute and chronic neurological and/or psychiatric disorders.