20954-21-6

Basic information

• Product Name: Butanoic acid, 2-[(3-chlorophenyl)hydrazono]-3-oxo-, ethyl ester
• CAS NO: 20954-21-6
• Molecular Formula: C12H13ClN2O3
• Molecular Weight: 268.7
• Mol File: 20954-21-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 2-[(3-chlorophenyl)hydrazono]-3-oxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 2-[(3-chlorophenyl)hydrazono]-3-oxo-, ethyl ester(20954-21-6)
• EPA Substance Registry System: Butanoic acid, 2-[(3-chlorophenyl)hydrazono]-3-oxo-, ethyl ester(20954-21-6)

Safety Data

• Hazardous Substances Data: 20954-21-6(Hazardous Substances Data)

Upstream product

• 100-77-6 3-chlorobenzenediazonium chloride 
• 141-97-9 ethyl acetoacetate 
• 108-42-9 3-chloro-aniline 
• 7732-18-5 water 

Downstream Products

• 77335-98-9 4-[(3-Chloro-phenyl)-hydrazono]-5-methyl-2-(pyridine-4-carbonyl)-2,4-dihydro-pyrazol-3-one 
• 143835-78-3 (Z)-4-(2-(3-Chlorophenyl)hydrazono)-3-methylisoxazol-5(4H)-one 
• 1493471-82-1 2-[1-(4-isobutylphenyl)ethyl]-5-methyl-4-[2-(3-chlorophenyl)hydrazinylidene]-2,4-dihydro-3H-pyrazol-3-one 
• 1282449-13-1 5-amino-3-(3-chlorophenyl)-N-isopropyl-4-oxo-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxamide 
• 1282449-10-8 5-amino-3-(3-chlorophenyl)-4-oxo-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxylic acid 
• 1062292-52-7 ethyl 5-amino-3-(3-chlorophenyl)-4-oxo-3,4-dihydrothieno-[3,4-d]pyridazine-1-carboxylate 
• 123534-18-9 ethyl 1-(3-chlorophenyl)-5-cyano-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate 
• 123534-17-8 5-Amino-3-(3-chloro-phenyl)-6-cyano-7-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-phthalazine-1-carboxylic acid ethyl ester 
• 735334-86-8 N-(5-acetyl-4-ethoxy-2-oxo-2,5-dihydro-imidazol-1-yl)-N-(3-chloro-phenyl)-acetamide 
• 137440-66-5 8-(3-Chloro-phenyl)-4-methyl-2,2,7,7-tetraoxo-1,2,7,8-tetrahydro-6H-3-oxa-2λ⁶,7λ⁶-dithia-1,6,8,8a-tetraaza-naphthalen-5-one 
• 132577-06-1 4-[(3-Chloro-phenyl)-hydrazono]-5-methyl-2-phthalazin-1-yl-2,4-dihydro-pyrazol-3-one 
• 137440-57-4 7-(3-Chloro-phenyl)-3-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-thia-2,5,7,7a-tetraaza-indene-4,6-dione 
• 70079-56-0 2-(4,6-dimethyl-pyrimidin-2-yl)-5-methyl-2H-pyrazole-3,4-dione 4-[(3-chloro-phenyl)-hydrazone] 

Relevant articles and documents

Discovery of a new class of sortase a transpeptidase inhibitors to tackle gram-positive pathogens: 2-(2-phenylhydrazinylidene)alkanoic acids and related derivatives

A FRET-based random screening assay was used to generate hit compounds as sortase A inhibitors that allowed us to identify ethyl 3-oxo-2-(2-phenylhydrazinylidene)butanoate as an example of a new class of sortase A inhibitors. Other analogues were generated by changing the ethoxycarbonyl function for a carboxy, cyano or amide group, or introducing substituents in the phenyl ring of the ester and acid derivatives. The most active derivative found was 3-oxo-2-(2-(3,4dichlorophenyl)hydrazinylidene)butanoic acid (2b), showing an IC50 value of 50 μM. For a preliminary assessment of their antivirulence properties the new derivatives were tested for their antibiofilm activity. The most active compound resulted 2a, which showed inhibition of about 60% against S. aureus ATCC 29213, S. aureus ATCC 25923, S. aureus ATCC 6538 and S. epidermidis RP62A at a screening concentration of 100 μM.

Type II diabetes-related enzyme inhibition and molecular modeling study of a novel series of pyrazolone derivatives

Inhibitors of alpha-Amylase are targets for the development of novel drugs for the treatment of diabetes and obesity. Alpha amylase is an enzyme which increases the bio availability of glucose in the blood. Hence, the inhibition effects of alpha amylase of 2-[1-(4-isobutylphenyl)ethyl]-5-methyl-4-[2-(aryl- substituted)hydrazinylidene]-2,4-dihydro-3H-pyrazol-3-one (4a-l) were investigated, among them compounds 4d, 4f, 4a, and 4g have displayed good inhibitory activity. The compounds with significant results were further evaluated for their molecular modeling study using in silico method. The new series of compounds were synthesized by solvent-free microwave irradiation method and were characterized by spectral and analytical data.

Aminothienopyridazine inhibitors of tau aggregation: Evaluation of structure-activity relationship leads to selection of candidates with desirable in vivo properties

Previous studies demonstrated that members of the aminothienopyridazine (ATPZ) class of tau aggregation inhibitors exhibit a promising combination of in vitro activity as well as favorable pharmacokinetic properties (i.e., brain-penetration and oral bioavailability). Here we report the synthesis and evaluation of several new analogues. These studies indicate that the thienopyridazine core is essential for inhibition of tau fibrillization in vitro, while the choice of the appropriate scaffold decoration is critical to impart desirable ADME-PK properties. Among the active, brain-penetrant ATPZ inhibitors evaluated, 5-amino-N-cyclopropyl-3-(4-fluorophenyl)-4-oxo-3,4- dihydrothieno[3,4-d]pyridazine-1-carboxamide (43) was selected to undergo maximum tolerated dose and one-month tolerability testing in mice. The latter studies revealed that this compound is well-tolerated with no notable side-effects at an oral dose of 50 mg/kg/day.