29211-70-9

Usage

Uses

Used in Pharmaceutical Industry:
3-N-PROPYL-2-PYRAZOLIN-5-ONE is used as a reactant in the preparation of 6-amino-5-cyanospiro-4-(piperidine-4'')-2H,4H-dihydropyrazolo[3,4-b]pyrans. These spiro compounds are of interest in the pharmaceutical industry due to their potential biological activities, such as anti-inflammatory, analgesic, and antipyretic properties. The synthesis of these compounds involves the use of 3-N-PROPYL-2-PYRAZOLIN-5-ONE as a key intermediate, highlighting its importance in the development of new drugs.

InChI:InChI=1/C6H10N2O/c1-2-3-5-4-6(9)8-7-5/h4H,2-3H2,1H3,(H2,7,8,9)

Upstream product

• 3249-68-1 ethyl butyroyl acetate 
• 30414-54-1 methyl 3-oxohexanoate 

Downstream Products

• 316360-38-0 6-amino-3-propyl-4-(thiophen-2-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile 
• 354554-34-0 6-amino-3-propyl-4-(2,3,4-trimethoxy-phenyl)-2,4-dihydro-pyrano[2,3-c]pyrazole-5-carbonitrile 
• 309724-93-4 6'-amino-3'-propyl-2-oxo-2'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile 
• 312509-91-4 C₁₈H₂₀N₄O₃ 
• 300393-93-5 6-amino-4-phenyl-3-propyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile 

Relevant academic research and scientific papers

Synthesis of new derivatives of pyrazol-chromeno[2,3-d]pyrimidine-ones by a one-pot three-component reaction

A new three-component reaction between salicylaldehydes, barbituric acid, pyrazolones, in the presence of para-toluenesulfonic acid, efficiently provides pyrazol-chromeno[2,3-d]pyrimidine-ones derivatives in good yields in ethanol/water at 70 °C. This mul

Screening, synthesis, crystal structure, and molecular basis of 6-amino-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles as novel AKR1C3 inhibitors

AKR1C3 is a promising therapeutic target for castration-resistant prostate cancer. Herein, an evaluation of in-house library discovered substituted pyranopyrazole as a novel scaffold for AKR1C3 inhibitors. Preliminary SAR exploration identified its derivative 19d as the most promising compound with an IC50 of 0.160 μM among the 23 synthesized molecules. Crystal structure studies revealed that the binding mode of the pyranopyrazole scaffold is different from the current inhibitors. Hydroxyl, methoxy and nitro group at the C4-phenyl substituent together anchor the inhibitor to the oxyanion site, while the core of the scaffold dramatically enlarges but partially occupies the SP pockets with abundant hydrogen bond interactions. Strikingly, the inhibitor undergoes a conformational change to fit AKR1C3 and its homologous protein AKR1C1. Our results suggested that conformational changes of the receptor and the inhibitor should both be considered during the rational design of selective AKR1C3 inhibitors. Detailed binding features obtained from molecular dynamics simulations helped to finally elucidate the molecular basis of 6-amino-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles as AKR1C3 inhibitors, which would facilitate the future rational inhibitor design and structural optimization.

POLYCYCLIC DERIVATIVES TARGETING RAL GTPASES AND THEIR THERAPEUTICAL APPLICATIONS

Contemplated compounds, compositions and methods are directed to Ral GTPase inhibitors with improved activity.

Synthesis of 4,5-dihydropyrazolyl-2H-indenediones by aldol condensation of ninhydrin with 1H-pyrazol-5-ol

A simple and efficient procedure for the synthesis of 2-hydroxy-2-(5-hydroxy-1H-pyrazol-4-yl)-2H-indene-1,3-dione derivatives, proceeding via aldol condensation between ninhydrin and various 3-alkyl-1H-pyrazol-5-ols is described. The syntheses were carried out in ethanol at room temperature and proceeded with short reaction times to give the products with high yields.

N,N-dialkyl-N′-chlorosulfonyl chloroformamidines in heterocyclic synthesis. Part VIII. Novel pyrazolo-fused oxathiadiazines and thiatriazoles

N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with pyrazol-3-ones 2 under a variety of conditions to give pyrazolo[2,3-e][1,2,3,5] oxathiadiazine dioxides 3 and pyrazolo[3,2-b][1,4,3,5]oxathiadiazine dioxides 5, and frequently, one or both of pyrazolo[1,2-b][1,2,3,5]thiatriazole 1,1,5-trioxides 4 and 1,1,7-trioxides 6. In all reactions, the pyrazolo[3,2-b][1,4,3,5]oxathiadiazine 5 was the major product, with the pyrazolo[2,3-e][1,2,3,5]oxathiadiazine 3 being a significant product in the absence of base. Prior to our recent work, the core ring systems of compounds 3 and 5 had not been reported and compounds 4 and 6 are new derivatives of a rare ring system. CSIRO 2010.

A new convenient four-component synthesis of 6-amino-2H,4H-pyrano[2,3-c] pyrazole-5-carbonitriles and one-pot synthesis of 6′-amino-5′-cyano- 1,2-dihydrospiro- [(3H)-indole-3,4′-(4′H)-pyrano[2,3-c]pyrazol]-2- ones

A new convenient method for the synthesis of 6-amino-2H,4H-pyrano[2,3-c] pyrazole-5-carbonitriles, namely, four-component condensation of carbonyl compounds (aromatic aldehydes, heterocyclic ketones), malononitrile, ss-keto esters, and hydrazine hydrate in ethanol in the presence of triethylamine as a catalyst, which occurs selectively, is developed. One-pot two-step modification of this method is proposed for the synthesis of spiro[(3H)-indole-3,4′-(4′H)-pyrano[2,3-c]pyrazol]-2-ones.

Kinase inhibitors

Compounds, pharmaceutical compositions, kits and methods are provided for use with kinases that comprise a compound of the formula: wherein R1, R2, R3, Q, U, V, W, X, and Y are as defined herein.

Microwave-assisted synthesis of substituted pyrazolones under solvent-free conditions

Condensation of hydrazine derivatives with various β-keto esters under solvent-free conditions using microwave irradiation leads to very rapid formation of pyrazolones with good to excellent yields.

QUINAZOLINE DERIVATIVES

The invention relates to the use of compounds of the formula I: wherein: ring C is a 5-6 membered heterocyclic moiety; Z is -O-, -S-, or -CH2-; R1 is hydrogen, C1-4alkyl, C1-4alkoxymethyl, di(C1-4)alkoxy)methyl, C1-4alkanoyl, trifluoromethyl, cyano, amino, C2-5alkenyl, C2-5alkynyl, carboxy, C3-7cycloalkyl, C3-7-cycloalkylC1-3alkyl, or an optionally substituted group selected from phenyl, benzyl, phenylC2-4alkyl and a 5-6 membered heterocyclic group; n is an integer from 0 to 5; m is an integer from 0 to 3; R2 represents hydrogen, hydroxy, halgeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3alkylsulphanyl, -NR3R4 (wherein R3 and R4, which may be the same or different, each represents hydrogen or C1-3alkyl), or R5X1- (wherein X1 represents a direct bond, -CH2-, or a heteroatom linker group and R5 is an alkyl, alkenyl or alkynyl chain optionally substituted by for example hydroxy, amino, nitro, alkyl, cycloalkyl, alkoxyalkyl, or an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, which alkyl, alkenyl or alkynyl chain may have a heteroatom linker group, or R5 is an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.