18794-98-4

Basic information

• Product Name: Butanoic acid, 2-[(4-bromophenyl)hydrazono]-3-oxo-, ethyl ester
• CAS NO: 18794-98-4
• Molecular Formula: C12H13BrN2O3
• Molecular Weight: 313.151
• Mol File: 18794-98-4.mol

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 2-[(4-bromophenyl)hydrazono]-3-oxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 2-[(4-bromophenyl)hydrazono]-3-oxo-, ethyl ester(18794-98-4)
• EPA Substance Registry System: Butanoic acid, 2-[(4-bromophenyl)hydrazono]-3-oxo-, ethyl ester(18794-98-4)

Safety Data

• Hazardous Substances Data: 18794-98-4(Hazardous Substances Data)

Upstream product

• 141-97-9 ethyl acetoacetate 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 5669-71-6 (Z)-4-(2-(4-bromophenyl)hydrazono)-3-methylisoxazol-5(4H)-one 
• 70220-83-6 4-(4-bromophenylhydrazono)-3-methyl-1-phenyl-4,5-dihydropyrazole-5-one 
• 1346005-99-9 C₂₁H₁₇BrN₆OS 
• 1310823-79-0 1-(6-chlorobenzothiazol-2-yl)-3-methyl-4-(4-bromophenylhydrazono)-2-pyrazolin-5-one 
• 1309479-16-0 C₁₇H₁₅BrN₄O₃S 
• 145484-19-1 ethyl 1-(4-bromophenyl)-5-cyano-4-methyl-6-oxo-1,6-dihydrodihydropyridazine-3-carboxylate 
• 126854-93-1 6-(4-Bromo-phenyl)-2-hydroxy-4,5-diphenyl-5,6-dihydro-4H-pyrano[2,3-d]pyridazine-3,8-dicarboxylic acid diethyl ester 
• 126837-39-6 2-Amino-6-(4-bromo-phenyl)-4,5-diphenyl-5,6-dihydro-4H-pyrano[2,3-d]pyridazine-3,8-dicarboxylic acid 8-ethyl ester 
• 126837-30-7 6-(4-Bromo-phenyl)-2,4,5-triphenyl-5,6-dihydro-4H-pyrano[2,3-d]pyridazine-8-carboxylic acid ethyl ester 
• 126854-92-0 3-Acetyl-6-(4-bromo-phenyl)-2-methyl-4,5-diphenyl-5,6-dihydro-4H-pyrano[2,3-d]pyridazine-8-carboxylic acid ethyl ester 
• 126837-32-9 6-(4-Bromo-phenyl)-2-methyl-4,5-diphenyl-5,6-dihydro-4H-pyrano[2,3-d]pyridazine-8-carboxylic acid ethyl ester 
• 126836-78-0 5-(4-Bromo-phenyl)-6-phenyl-5,6-dihydro-1H-pyrazolo[4,3-c]pyridazin-3-ol 
• 136920-60-0 6-Bromo-3-(1-{[4-phenyl-3H-thiazol-(2Z)-ylidene]-hydrazono}-ethyl)-cinnolin-4-ol 
• 86380-71-4 4-Benzoyl-1-(4-bromo-phenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 

Relevant articles and documents

Synthesis and bioevaluation study of novel N-methylpicolinamide and thienopyrimidine derivatives as selectivity c-Met kinase inhibitors

Four series of N-methylpicolinamide moiety and thienopyrimidine moiety bearing pyridazinone were designed and synthesized and evaluated for the IC50 values against three cancer cell lines (A549, HepG2 and MCF-7) and some selected compounds were

Discovery of novel pyrrolo-pyridine/pyrimidine derivatives bearing pyridazinone moiety as c-Met kinase inhibitors

In continue to our previous research, eight series of pyrrolo[2,3-b]pyridine and pyrrolo[2,3-d]pyrimidine derivatives bearing pyridazinone moiety were designed, synthesized, and the in vitro antitumor activity was evaluated against four cancer cell lines (A549, HepG2, MCF-7 and PC-3). Some selected compounds (22f, 22g, 26c and 26e) were evaluated for the activity against c-Met kinase, and according to the results of kinase inhibitory activity, the compound 22g was further evaluated for other four tyrosine kinases (Flt-3, VEGFR-2, c-Kit and EGFR) to test the enzyme-based selectivity. The most promising compound 22g showed excellent activity than lead compound Foretinib against A549, HepG2, MCF-7 and PC-3 cell lines, with the IC50 values of 2.19 ± 0.45 μM, 1.32 ± 0.26 μM, 6.27 ± 1.04 μM and 4.63 ± 0.83 μM. The structure–activity relationships (SARs) and docking studies indicated that the pyrrolo[2,3-b]pyridine derivatives bearing 4-oxo-pyridazinone moiety was superior to the pyrrolo[2,3-d]pyrimidine derivatives bearing 6-oxo-pyridazinone moiety. What's more, the target compounds modified with X and Y (X = H, Y = H) were favorable to the activity. And electron drawing groups (EWGs) of 4-Cl-3CF3 on the aryl group show the best activity.

Synthesis and antidiabetic evaluation of novel pyrazolone derivatives

Ethyl-2-[diazo(substituted benzene) acetoacetates (2a-h) were treated with benzhydrazide (3) to yield the title compounds pyrazolone derivatives (4a-h). All the new compounds were characterized by IR, 1H-NMR, Mass and elemental analysis. The title compounds were subjected to in-vitro antidiabetic activity by α-amylase and α-glucosidase inhibitory activity. Compounds 4b and 4c showed good antidiabetic activity when compared to the standard drug acarbose.

Microwave assisted synthesis and biological activity of 4-(2-(aryl substituted) hydrazono)-1-(2-(p-tolyloxyacetyl)-3-methyl-1H-pyrazol- 5-one

A novel series of 4-(2-(aryl substituted) hydrazono)-1-(2-(p-tolyloxy) acetyl)-3-methyl- 1H-pyrazol-5-ones 3(a-j) was prepared by the reaction of ethyl-2-arylhydrazono -3- oxobutyrate and p-tolyloxyacethydrazide under microwave irradiation. The structures of the synthesized compounds were established by their spectral and analytical data. All the new compounds were screened for their antibacterial and antifungal activity.

Regioselective CC bond cleavage in arylhydrazones of 4,4,4-trifluoro-1- (thiophen-2-yl)butane-1,3-diones

New (Z)-2-(2-(para-substituted phenyl)hydrazono)-4,4,4-trifluoro-1- (thiophen-2-yl)butane-1,3-diones with chloro (1), bromo (2) and carboxy (3) substituents were synthesized and characterized by ESI-MS, IR, 1H and 13C NMR spectroscop

Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: Design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties

A novel series of phenyl hydrazone bearing pyrazole and pyrimidine hybrid compounds has been designed using the molinspiration toolkit based on Lipinski's rule of five and developed via sequential reactions starting from the diazotization of different anilines and further active methylation with acetyl acetone, ethyl acetoacetate and ethyl cyanoacetate to generate hydrazono derivatives. The target hybrid compounds were synthesized on cyclisation of the resulting hydrazono derivatives with hydrazine, phenyl hydrazine and urea. These molecules have been subsequently tested for anti-HIV activity using TZM-bl cell lines. The MTT assay was also carried out for the cytotoxicity determination of the active compounds. Further, to exemplify the key structural features of the molecules, a molecular docking analysis of the most active compounds was performed at the NNIBP of the HIV-RT protein. The antibacterial activity of the target compounds was also determined against a panel of four Gram-positive and four Gram-negative human pathogens. All molecules showed a potent anti-HIV activity along with a prominent inhibition of bacterial organisms.

Synthesis and antimicrobial activity of pyrazolinones and pyrazoles having benzothiazole moiety

A new class of 4-arylhydrazono-1-benzothiazolyl-3-methylpyrazolin-5-ones (3a-j) and 4-arylazo-1-benzothiazolyl-3,5-dimethylpyrazoles (4a-j) were designed as pharmacophore hybrids between pyrazolinone/pyrazole and benzothiazole moiety. The target molecules were efficiently synthesized by the cyclization of various oxobutyrates/pentane-2,4-dione derivatives with 6-chloro-2- hydrazinobenzothiazole in the presence of glacial acetic acid. The compounds were evaluated for their in vitro antimicrobial activity. Preliminary study of the structure-activity relationship revealed that electron-withdrawing groups in phenyl ring had a promising effect on the antimicrobial activity. Also, correlation study has been used to establish the relationships between the antibacterial activity and physicochemical parameter clogP. Springer Science+Business Media, LLC 2011.

AMINOTHIENOPYRIDAZINE INHIBITORS OF TAU ASSEMBLY

The present invention is directed to methods of inhibiting a tauopathy in a patient by administration of a compound of formula (I): Novel aminothienopyridazine compounds are also described.

Synthesis, characterization and antibacterial screening of new pyrazole and pyrazoline-5-one derivatives

A series of N′-(p-toluene sulphonyl)-3-methyl-4-(substituted arylhydrazono)-2-pyrazoline-5-ones and N′-(2-hydroxybenzoyl)-3,5-dimethyl- 4-(substituted arylazo)pyrazoles have been synthesized and characterized by chemical analysis, IR and 1H NMR spectral data. The compounds have been screened for antibacterial activity against Staphylococcus aureus and Escherichia coli.

Discovery of brain-penetrant, orally bioavailable aminothienopyridazine inhibitors of Tau aggregation

Agents capable of preventing the misfolding and sequestration of the microtubule-stabilizing protein tau into insoluble fibrillar aggregates hold considerable promise for the prevention and/or treatment of neurodegenerative tauopathies such as Alzheimer's