62455-70-3

Usage

Uses

Used in Pharmaceutical Industry:
3-CYCLOHEXYL-3-OXOPROPANENITRILE is used as a chemical intermediate for the preparation of pyrazoloquinazolinone derivatives, which act as PARP-1 inhibitors. These inhibitors play a crucial role in the development of anticancer drugs, as they target and inhibit the activity of poly(ADP-ribose) polymerase-1 (PARP-1), an enzyme involved in DNA repair and cell survival. This inhibition can lead to the death of cancer cells and enhance the effectiveness of chemotherapy.
Additionally, 3-CYCLOHEXYL-3-OXOPROPANENITRILE is used in the preparation of benzoxazoyl amino cyanopyrimidines, which function as negative allosteric modulators of the mGlu5 receptor. These modulators have potential therapeutic applications in the treatment of neurological and psychiatric disorders, such as anxiety, depression, and addiction. By modulating the activity of the mGlu5 receptor, these compounds can help regulate neurotransmission and alleviate symptoms associated with these conditions.

InChI:InChI=1S/C9H13NO/c10-7-6-9(11)8-4-2-1-3-5-8/h8H,1-6H2

Upstream product

• 4630-82-4 methyl cyclohexylcarboxylate 
• 75-05-8 acetonitrile 
• 3289-28-9 ethyl cyclohexanecarboxylate 
• 372-09-8 cyanoacetic acid 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 1116-98-9 cyanoacetic acid tert-butyl ester 
• 98-89-5 Cyclohexanecarboxylic acid 
• 823-76-7 Cyclohexyl methyl ketone 
• 7677-24-9 trimethylsilyl cyanide 
• 119612-85-0 {[1-cyclohexylethenyl]oxy}trimethylsilane 

Downstream Products

• 81542-54-3 3-cyclohexyl-1H-pyrazol-5-amine 
• 95882-34-1 (Z)-3-Amino-3-cyclohexyl-acrylonitrile 
• 7560-69-2 1-cyclohexyl-2-propyn-1-one 
• 394647-20-2 (Z)-2-(3,3-dimethyl-3,4-dihydro-(2H)-isoquinolin-1-ylidene)-1-cyclohexylethan-1-one 
• 500766-46-1 3-cyclohexyl-5-aminoisoxazole 
• 126679-00-3 3-amino-1-cyclohexylpropan-1-ol 
• 198561-32-9 (S)-3-cyclohexyl-3-hydroxypropanenitrile 
• 92587-21-8 Methyl (R)-α-hydroxycyclohexaneacetate 
• 53585-93-6 (R)-(-)-hexahydromandelic acid 
• 39140-53-9 2,2-dichloro-1-cyclohexylethanone 
• 95882-45-4 (Z)-3-Amino-3-cyclohexyl-thioacrylamide 
• 95882-24-9 3-Cyclohexyl-isothiazol-5-ylamine 
• 100287-22-7 3-Cyclohexyl-1,6-dimethyl-4-(2-nitro-phenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 2-phenoxy-ethyl ester; hydrochloride 
• 93181-13-6 3-Cyclohexyl-1,6-dimethyl-4-(2-nitro-phenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester; hydrochloride 

Relevant academic research and scientific papers

Nitrogen-containing ring derivative inhibitor as well as preparation method and application thereof

The invention relates to a nitrogen-containing ring derivative inhibitor as well as a preparation method and an application thereof. In particular, the present invention relates to a compound represented by general formula (I), a preparation method thereof, a pharmaceutical composition containing the compound, and uses of the compound as a P2X3 inhibitor in treatment of P2X3 receptor dysfunction diseases, especially in treatment of neurogenic diseases.

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.

NOVEL PYRAZOLO-PYRROLO-PYRIMIDINE-DIONE DERIVATIVES AS P2X3 INHIBITORS

The present invention covers substituted Pyrazolo-pyrrolo-pyrimidine-dione (PPPD) compounds of general formula (I): in which R1, R2 and R3 are as defined herein, methods of preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of neurogenic diseases, as a sole agent or in combination with other active ingredients.

A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones

The acylation of the acetonitrile anion with lactones and esters in ethereal solvents was successfully exploited using inexpensive KOt-Bu to obtain a variety of β-ketonitriles and trifunctionalized building blocks, including useful O-unprotected diols. It was discovered that lactones react to produce the corresponding derivatized cyclic hemiketals. Furthermore, the addition of a catalytic amount of isopropanol, or 18-crown-6, was necessary to facilitate the reaction and to reduce side-product formation under ambient conditions.

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.

One-pot dichlorinative deamidation of primary β-ketoamides

An approach to the dichlorinative deamidation of primary β-ketoamides through ketonic cleavage is described, and a series of α,α-dichloroketones were furnished mostly in the presence of TEMPO. Based on control experiments, a mechanism involving tandem dichlorination and deamidation is proposed to interpret the observed reactivity.

Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers

An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.

Chemo- And stereoselective reduction of β-keto-α-oximino nitriles by using baker's yeast

The baker's yeast mediated reduction of β-keto-α-oximino nitriles 3 at 20 ° C gave β-hydroxy-α-oximino nitriles 4 in high yields with high enantiomeric purity [enantiomeric excess (ee) values >99%]. At room temperature, the same reaction afforded the product in a slightly lower yield. The β-hydroxy-α-oximino nitriles 4 were obtained as single stereoisomers according to chiral GC-MS analyses and the 1H and 19F NMR spectra of the corresponding Mosher esters. The abso-lute stereochemistry of alcohol 4a was determined by hydrolysis of its oximino nitrile group followed by conversion into its corresponding α-hydroxy ester. The β-hydroxy-α-oximino nitrile products were further submitted to oxime- and nitrileselective transformations. This chemo- and stereoselective reduction can be used to generate important chiral building blocks.

AURORA KINASE INHIBITORS

Disclosed herein inter alia are compositions and methods useful in the treatment of cancer and for modulating the activity of Aurora A kinase and/or a Myc family protein.

PYRIDO PYRIMIDINES

Compounds of formula and pharmaceutically acceptable salts thereof are described, as well as the pharmaceutical compositions containing said compounds and their pharmaceutically acceptable salts, and the use of said compounds and pharmaceutical compositions for the treatment, control or amelioration of proliferative diseases, including cancer, Down syndrome or early onset Alzheimer's disease.