4149-06-8

Usage

Chemical Properties

BEIGE POWDER

InChI:InChI=1/C9H9N3O/c10-8-6-9(13)12(11-8)7-4-2-1-3-5-7/h1-5H,6H2,(H2,10,11)

Upstream product

• 6152-31-4 phenyl hydrazine hydrate 
• 105-56-6 ethyl 2-cyanoacetate 
• 62-53-3 aniline 
• 84104-44-9 5-Methyl-3-(2-oxo-2-anilinoethyl)-1,2,4-oxadiazole 
• 61239-31-4 3-Oxo-3-anilinopropionamidoxime 
• 621-03-4 cyanoacetanilide 
• 2311-90-2 3-(Acetylamino)-1-phenyl-2-pyrazolin-5-one 
• 99365-97-6 3-Amino-4-(p-N,N-dimethylamino)phenylmethyliden-2-pyrazolin-5-on 
• 79852-93-0 3-Nitro-3-(phenyl-hydrazono)-propionic acid ethyl ester 

Downstream Products

• 71290-80-7 pyrazolo<3,4-b>pyridine-3,6-dione 
• 62208-81-5 3-amino-5-chloro-1-phenylpyrazole-4-carboxaldehyde 
• 1266714-02-6 (5-methyl-2-oxo-1-phenyl-2,4-dihydro-1H-pyrazolo[1,5-a]pyrimidin-7-ylidene)acetic acid butyl ester 
• 863880-27-7 4,6-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 1204822-77-4 1-(2-bromoethyl)-4,6-dimethyl-2-phenyl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one 
• 1204822-78-5 1-(2-(hexanhydropyrido[1,2-a][1,4]diazepin-2(1H,3H,7H)-yl)ethyl)-4,6-dimethyl-2-phenyl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one 
• 1266714-05-9 2-(1-allyl-6-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[3,4-b]pyridin-4-yl)acetic acid butyl ester 
• 1266714-08-2 1-allyl-4,6-dimethyl-2-phenyl-1,2-dihydro-1H-pyrazolo[3,4-b]pyridin-3-one 
• 1266714-10-6 1-allyl-4,6-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 1266714-11-7 4,6-dimethyl-3-oxo-2-phenyl-1-prop-2-ynyl-2,3-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 1266714-13-9 2-(1,4-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[3,4-b]pyridin-6-yl)acetic acid butyl ester 
• 1266714-16-2 C₂₀H₂₃N₃O₃ 
• 71290-77-2 4,6-dimethyl-2-phenyl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one 

Relevant academic research and scientific papers

Design, Synthesis, and Characterization of Some Hybridized Pyrazolone Pharmacophore Analogs against Mycobacterium tuberculosis

Twenty-seven hybridized pyrazolone analogs were designed, docked, synthesized in two series and evaluated for their in vitro antimycobacterial properties. In the first series, four Schiff base derivatives, 6b, 7b, 7h, and 7i, show good antitubercular activity with minimum inhibition concentration (MIC) values in the range of 32.56-42.55 μM. In the second series, two compounds, 8b and 8c, possessed significant antitubercular activity with MIC 630. Compounds 8b and 8c showed shikimate kinase inhibition activity at 5.84 and 6.93 μM, respectively. The activity and docking results lead to the conclusion that the compounds without double bond in the imine side chain and hydrophobic clashes at the pyrazolone end are necessary for good accommodation in the binding pocket and for imparting flexibility. All the compounds were also tested for antimicrobial activity (antibacterial and antifungal) and show highly significant activities against all the microorganisms tested. Hybridized pyrazolone analogs were designed, docked, and synthesized in two series. Both compound series were evaluated for their in vitro antimycobacterial properties, showing highly significant activities against all microorganisms tested. No double bond in the imine side chain and hydrophobic clashes at the pyrazolone end were necessary for good accommodation in the binding pocket of shikimate kinase.

Investigations on the Hydrolytic Stability of 4-Arylmethylidene-2-pyrazolin-5-ones

The 4-Arylmethylidene-2-pyrazoline-5-ones S are not stable under aqueous alkaline conditions.By the substitution of R3 with electron donor substituents S reacts preferably yielding aldehyde A and 2-pyrazoline-5-one P, while with electron acceptor substituents S forms 4,4'-arylmethylidene-bis-2-pyrazoline-5-one B.The intermediate of hydrolysis is 4-(arylhydroxymethyl)-2-pyrazoline-5-one SOH.The second order rate constants of the reactions of S with hydroxidions and with 2-pyrazoline-5-ones P(-) are determined.The dependence of the hydrolytic decomposition of S on the pH value, substituents and temperature is suitable for the intermediate formation of SOH.

A New Synthesis of 3-Amino-1-aryl-2-pyrazolin-5-ones

Reaction of ethyl 3-nitropropionate with aryldiazonium chlorides in basic medium yields ethyl 3-nitro-3-(arylhydrazono)propionates.These α-nitrohydrazones are converted by catalytic hydrogenation to 3-amino-1-aryl-2-pyrazolin-5-ones, probably via cyclization of intermediate amidrazones produced in situ.This appears to be the first route to the title compounds that does not use a substituted phenyl hydrazine intermediate and offers advantages in the preparation of pyrazolinones bearing electron-rich aryl rings.