6944-29-2

Basic information

• Product Name: 3-hydroxy-4-[(4-methylphenyl)hydrazono]cyclohexa-2,5-dien-1-one
• CAS NO: 6944-29-2
• Molecular Formula: C₁₃H₁₂N₂O₂
• Molecular Weight: 228.2466
• Mol File: 6944-29-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 383.1°C at 760 mmHg
• Flash Point: 185.5°C
• Density: 1.21g/cm³
• Vapor Pressure: 1.49E-06mmHg at 25°C
• Refractive Index: 1.607
• CAS DataBase Reference: 3-hydroxy-4-[(4-methylphenyl)hydrazono]cyclohexa-2,5-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-4-[(4-methylphenyl)hydrazono]cyclohexa-2,5-dien-1-one(6944-29-2)
• EPA Substance Registry System: 3-hydroxy-4-[(4-methylphenyl)hydrazono]cyclohexa-2,5-dien-1-one(6944-29-2)

Safety Data

• Hazardous Substances Data: 6944-29-2(Hazardous Substances Data)

Upstream product

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Relevant articles and documents

Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies

In the present study, a series of azo derivatives (TR-1 to TR-9) have been synthesised via the diazo-coupling approach between substituted aromatic amines with phenol or naphthol derivatives. The compounds were evaluated for their therapeutic applications against alpha-glucosidase (anti-diabetic) and pathogenic bacterial strains E. coli (gram-negative), S. aureus (gram-positive), S. aureus (gram-positive) drug-resistant strain, P. aeruginosa (gram-negative), P. aeruginosa (gram-negative) drug-resistant strain and P. vulgaris (gram-negative). The IC50 (μg/mL) of TR-1 was found to be most effective (15.70 ± 1.3 μg/mL) compared to the reference drug acarbose (21.59 ± 1.5 μg/mL), hence, it was further selected for the kinetic studies in order to illustrate the mechanism of inhibition. The enzyme inhibitory kinetics and mode of binding for the most active inhibitor (TR-1) was performed which showed that the compound is a non-competitive inhibitor and effectively inhibits the target enzyme by binding to its binuclear active site reversibly.

Synthesis and antimicrobial studies of new antibacterial azo-compounds active against staphylococcus aureus and listeria monocytogenes

Some novel (phenyl-diazenyl)phenols (4a–m) were designed and synthesized to be evaluated for their antibacterial activity. Starting from an active previously-synthesized azobenzene chosen as lead compound, we introduced some modifications and optimization of the structure, in order to improve solubility and drug conveyance. Structures of all newly-synthesized compounds were confirmed by 1H nuclear magnetic resonance (NMR), mass spectrometry, and UV-Vis spectroscopy. Antibacterial activity of the new compounds was tested with the dilution method against the bacteria strains Listeria monocytogenes, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa PAO1. All the compounds were selectively active against Gram-positive bacteria. In particular, compounds 4d, 4h, and 4i showed the highest activity against S. aureus and Listeria monocytogenes, reaching remarkable MIC100 values of 4 μg/mL and 8 μg/mL. The relationship between antimicrobial activity and compound structure has suggested that the presence of hydroxyl groups seems to be essential for antimicrobial activity of phenolic compounds.

Synthesis of diaryl-azo derivatives as potential antifungal agents

As compared with a commercially available agricultural fungicide hymexazol, some phenyl-azo phenol derivatives (e.g., 4a, 4b, 4f, 4n, 4q, 4u, and 4v) exhibited the more promising and pronounced antifungal activities in vitro against seven phytopathogenic fungi. It seemed that 4-((un)substituted phenylazo)-phenol and 4-((un)substituted phenylazo)-3-methylphenol might be considered as new lead structures for further design of agricultural fungicides.