33279-01-5

Usage

Uses

Used in Chemical Synthesis:
3-OXO-PENTANENITRILE is used as a key intermediate in the synthesis of various organic compounds, particularly in the pharmaceutical and agrochemical industries. Its ability to undergo a range of chemical reactions, such as reduction, hydrolysis, and condensation, makes it a versatile building block for the development of new molecules with potential biological activities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-OXO-PENTANENITRILE is used as a starting material for the synthesis of various drug candidates. Its unique structural features allow for the development of novel therapeutic agents with improved pharmacological properties, such as enhanced potency, selectivity, and bioavailability.
Used in Agrochemical Industry:
3-OXO-PENTANENITRILE is also utilized in the agrochemical industry for the synthesis of bioactive compounds with potential applications as pesticides, herbicides, and insecticides. Its structural diversity and reactivity enable the design of new molecules with improved efficacy and selectivity against target pests and weeds.

InChI:InChI=1/C5H7NO/c1-2-5(7)3-4-6/h2-3H2,1H3

Upstream product

• 105-37-3 Ethyl propionate 
• 75-05-8 acetonitrile 
• 90087-51-7 2-Cyano-3-oxo-pentanoic acid ethyl ester 
• 13284-42-9 2-pentenenitrile 
• 554-12-1 propanoic acid methyl ester 
• 79-03-8 propionyl chloride 
• 105-56-6 ethyl 2-cyanoacetate 
• 616-27-3 1-chlorobutan-2-one 
• 151-50-8 potassium cyanide 

Downstream Products

• 4949-44-4 ethyl propanoylacetate 
• 77479-49-3 5-amino-3-ethylisoxazole 
• 1904-24-1 5-ethyl-3-amino-1H-pyrazole 
• 1904-24-1 5-ethyl-2H-pyrazol-3-ylamine 
• 137628-85-4 3-Methyl-5-phenyl-2,4-dioxo-1-cyclohexancarbonitril 
• 1226176-50-6 3-ethyl-1-(2-methylphenyl)-1H-pyrazol-5-amine 
• 198561-27-2 (R)-3-hydroxypentanenitrile 
• 1226191-26-9 3-ethyl-1-(p-tolyl)-1H-pyrazol-5-amine 
• 1207895-42-8 (E)-2-benzylidene-3-oxopentanenitrile 
• 1159001-69-0 3-(p-tolylamino)pent-2-enenitrile 
• 19754-80-4 5-ethyl-1,2-oxazol-3-amine 
• 943906-32-9 2-[(2-chloro-phenyl)-hydrazono]-3-oxo-pentanenitrile 
• 943906-29-4 2-[(4-chloro-phenyl)-hydrazono]-3-oxo-pentanenitrile 
• 943906-33-0 3-oxo-2-(p-tolyl-hydrazono)-pentanenitrile 

Relevant academic research and scientific papers

Synthesis and anticonvulsant activity of enaminones. 4. Investigations on isoxazole derivatives

Due to the exceptional anticonvulsant activity displayed by substituted aniline enaminones, related pyridine derivatives and phenothiazines synthesised in our laboratories, the further investigation of various aromatic heterocycles was undertaken. Condensation of cyclic 1,3-diketo esters with 3-, and 5-aminoisoxazole derivatives led to a series of potent anti-maximal electroshock (MES) analogues, three of which occurred in the 3-amino series: ethyl ester (10), orally (po) active in rats [ED50 68.9 mg kg-1, TD50>500 mg kg-1, protective index (PI=TD50/ED50)>49.6]; methyl ester (9), ED50 68.9 mg kg-1 intraperitoneally (ip) in mice, TD50>500 mg kg-1, PI>7.3, and tert-butyl ester (8), ED50 28.1 mg kg-1 po in rats, TD50>500 mg kg-1, PI>17.8. Sodium channel binding studies, as well as evaluations against pentylenetetrazol, bicuculline, and picrotoxin on isoxazole 10 were all negative, leading to an unknown mechanism of action. X-ray diffraction patterns of a representative of the 3-amino series (isoxazoles 6-11) unequivocally display the existence of intramolecular hydrogen bonding of the nitrogen to the vinylic proton in the cyclohexene ring, providing a pseudo three ring structure which was also shown previously with the vinylic benzamides. Physicochemical-permeability across the BBB suggested an efflux mechanism for the previously synthesised aniline enaminones, but not with isoxazole 10.

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.

Discovery of 2,4-diaminopyrimidine derivatives targeting p21-activated kinase 4: Biological evaluation and docking studies

In this study, novel 2,4-diaminopyrimidine derivatives targeting p21-activated kinase 4 (PAK4) were discovered and evaluated for their biological activity against PAK4. Among the derivatives studied, promising compounds A2, B6, and B8 displayed the highest inhibitory activities against PAK4 (IC50 = 18.4, 5.9, and 20.4 nM, respectively). From the cellular assay, compound B6 exhibited the highest potency with an IC50 value of 2.533 μM against A549 cells. Some compounds were selected for computational ADME (absorption, distribution, metabolism, and elimination) properties and molecular docking studies against PAK4. The detailed structure–activity relationship based on the biochemical activities and molecular docking studies were explored. According to the docking studies, compound B6 had the lowest docking score (docking energy: ?7.593 kcal/mol). The molecular docking simulation indicated the binding mode between compound B6 and PAK4. All these results suggest compound B6 as a useful candidate for the development of a PAK4 inhibitor.

Application of 5-aminopyrazole compounds to plant growth regulation aspect

The invention discloses application of 5-aminopyrazole compounds to plant growth regulation aspect in the technical field of pesticide compounds, in particular to application of the 5-aminopyrazole compounds shown by the formula to the plant growth regulation aspect, particularly the application to the plant growth inhibition. The formula I is shown in the description. The compound shown in the formula I can be used as a weedicide; weeds in places such as highway and railway can be killed through regulating the concentration of the 5-aminopyrazole compounds, wherein the R1 is hydrogen or alkylor phenyl or substituted phenyl; R2 is alkyl; R3 is hydrogen or halogen.

Preparation of 3,4-Substituted-5-Aminopyrazoles and 4-Substituted-2-Aminothiazoles

3,4-Substituted-5-aminopyrazoles and 4-substituted-2-aminothiazoles are frequently used intermediates in medicinal chemistry and drug discovery projects. We report an expedient flexible synthesis of 3,4-substituted-5-aminopyrazoles (35 examples), based on palladium-mediated α-arylation of β-ketonitriles with aryl bromides. A library of 4-substituted-2-aminothiazoles (21 examples) was assembled by a sequence employing Suzuki coupling of newly prepared, properly protected pinacol ester and MIDA ester of 4-boronic acid-2-aminothiazole with (hetero)aryl halides.

New trisubstituted cyanopyrazoles and cyanoscorpionates

New syntheses are reported to give pyrazoles with cyano substituents at the 4-position of the pyrazole ring and ethyl or isopropyl substituents at the 3-position, as well as pyrazoles with cyano substituents at the 4-position and alkyl/aryl/bromo substituents at both the 3- and 5-positions. Synthesis of scorpionates using tetradecane as a high-boiling solvent has been shown to be more efficient than the melt method and has led to new scorpionates using the newly synthesized pyrazoles. An unexpected complex is isolated in which the Ni(cyclam)2+moiety crystallizes with two cyanoscorpionates as counterions, without binding of the scorpionate ligands to the Ni atom.

Dihydro pyridine compound, its composition, preparation method and use

Disclosed dihydropyridine compounds are the compounds possessing the following general formula (I) as shown in the specification, wherein R1 is selected from hydrogen, halogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, alkylamino, substituted alkylamino, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic groups, substituted heterocyclic groups, ester group and amide group; R2 is selected from hydrogen, cyanogroup, alkyl, substituted alky, alkenyl, substituted alkenyl and acyl; or R2 and R3 form a fused ring; R3 is selected from alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl; or R3 and R2 or R4 form a fused ring; R4 is selected from hydrogen, alkyl and substituted alkyl; or R4 and R3 or R5 form a fused ring; R5 is selected form alkyl, substituted alky, aryl, substituted aryl, heteroaryl and substituted heteroaryl; or R5 and R4 form a fused ring. The invention also discloses a preparation method of the compounds of the general formula (I), compositions containing the compounds of the general formula (I), and applications of the compositions to medicaments for treating cancers.

Pyrazolotriazines as inhibitors of nucleases

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3 and R4 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

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.