6944-29-2Relevant academic research and scientific papers
Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies
Tahir, Tehreem,Shahzad, Mirza Imran,Tabassum, Rukhsana,Rafiq, Muhammad,Ashfaq, Muhammad,Hassan, Mubashir,Kotwica-Mojzych, Katarzyna,Mojzych, Mariusz
, p. 1509 - 1520 (2021/07/16)
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.
Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions
Davis, Garrett J.,Townsend, Julia A.,Morrow, Madeline G.,Hamie, Mohamed,Shepard, Abigail J.,Hsieh, Chih-Chieh,Marty, Michael T.,Jewett, John C.
, p. 2432 - 2438 (2021/11/18)
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
Piotto, Stefano,Concilio, Simona,Sessa, Lucia,Diana, Rosita,Torrens, Gabriel,Juan, Carlos,Caruso, Ugo,Iannelli, Pio
, (2017/08/29)
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.
An experimental and theoretical study on influence of H-bonding on the synthesized azo derivatives structures
Amiri, Rahebeh,Haghdadi, Mina,Golshani, Ashkan,Amiri, Maryam Mohamadian,Barikani, Maryam
, p. 45 - 52 (2013/03/28)
We have reported a simple and efficient reaction for the synthesis of some new functionalized azo structures which were prepared by electron deficient acetylenic compounds in the presence of triphenylphosphine. The characterization of the synthesized azo compounds has been determined by FTIR, UV-Vis, 1H NMR, 13C NMR andMass spectroscopic techniques. The influence of H-bonding on the products has been shown by different experimental analysis. Also, the regioselectivity of the reaction, tautomerization equilibrium and the stability of products was investigated using DFT calculations at the B3LYP/6-31G level of theory.
Synthesis of diaryl-azo derivatives as potential antifungal agents
Xu, Hui,Zeng, Xiwen
supporting information; experimental part, p. 4193 - 4195 (2010/08/22)
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.
