15310-69-7

Upstream product

• 17333-79-8 p-methoxybenzenediazonium 
• 108-46-3 recorcinol 
• 104-94-9 4-methoxy-aniline 
• 74148-29-1 1-((4-methoxyphenyl)diazenyl)piperidine 
• 4346-59-2 para-methoxyphenyldiazonium chloride 

Downstream Products

• 128953-40-2 {Cu(C₆H₃(OH)(O)NNC₆H₄(OCH₃))2} 
• 59360-34-8 4,4'-dimethoxy-2-hydroxyazobenzene 

Relevant academic research and scientific papers

Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions

This work describes the development of phenyl diazenyl piperidine triazene derivatives that can be activated to release aryl diazonium ions for labeling of proteins using light. These probes show marked bench stability at room temperature and can be photoisomerized via low-intensity UVA irradiation at physiological pH. Upon isomerization, the triazenes are rendered more basic and readily protonate to release reactive aryl diazonium ions. It was discovered that the intensity and duration of the UV light was essential to the observed diazonium ion reactivity in competition with the traditionally observed photolytic radical pathways. The combination of their synthetic efficiency coupled with their overall stability makes triazenes an attractive candidate for use in bioconjugation applications. Bioorthogonal handles on the triazenes are used to demonstrate the ease by which proteins can be modified.

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.

Design, synthesis and antibacterial activities of new azo-compounds: An experimental and a computational approach

Azo-compounds, with the general formula R-N=N-R' (where R and R' can be either aryl or alkyl groups), constitute an important class of organic dyes. Over the past decades, these compounds have attained increasing attention of the scientific community because of their immense biological as well as industrial applications. Methodology: A series of new azo-compounds was prepared starting from 4-aminophenol and 4-methoxyaniline under standard conditions. The synthesized compounds were investigated for their potential as antibacterial agents. The bacterial strains used were Escherichia coli, Streptococcus pyrogenes, Shigellasonnei, Neisseria gonorrhoeae and Staphylococcus aureus. Results and Discussion: The structures of newly synthesized compounds were established by usual spectroscopic techniques such as UV-Vis, FTIR, Mass Spectrometry and NMR spectroscopy. These results were further supported by molecular docking studies in order to confirm the binding interaction of the compounds with bacterial proteins. Furthermore, these compounds were also investigated by density functional theory calculations. The calculated band gap (Egap) of the targeted library was found between the ranges of 0.12307-13665 eV. Conclusion: In summary, we have synthesized and characterized an interesting series of azo-compounds which have potent anti-bacterial activities against several bacterial species. The experimental results were further supported by molecular docking analysis and density functional theory calculations.

Synthesis of new metallomesogens containing Ni(II) and Cu(II) atoms

A few new metallomesogens containing Ni(II) and Cu(II) atoms of the ligands 4-substituted 2′-hydroxy 4′(4″-n-hexadecyloxybenzoloxy)azobenzenes have been synthesized. The complexes have been characterized by C, H, N, microanalysis, IR, NMR and UV-Visible spectroscopies. Meso-morphic properties of all the ligands and complexes were investigated on a Leitz Laborlux 12 POL microscope provided with a heating stage.