936-02-7Relevant articles and documents
New nano-complexes of Zn(II), Cu(II), Ni(II) and Co(II) ions; spectroscopy, thermal, structural analysis, DFT calculations and antimicrobial activity application
El-Shafiy, Hoda F.,Saif,Mashaly, Mahmoud M.,Halim, Shimaa Abdel,Eid, Mohamed F.,Nabeel,Fouad
, p. 452 - 461 (2017)
This work presents synthesis, characterization, and application of several metal (II) complexes with (E)-2-hydroxy-N/-((thiophen-2-yl)methylene)benzohydrazide (H2L). Prepared complexes were identified by elemental, thermal, FT-IR, UV–Vis, 1H NMR, and XRD analysis, as well as molar conductivity and magnetic moment measurements. Changes in FT-IR and 1H NMR spectra of hydrazone ligand upon coordination indicated that the ligand behaves the same way as a monoanonic ligand with ONS donor sites. Kinetic parameters were determined for each thermal degradation stage of the ligand and its complexes using ‘Coats–Redfern’ method. All results confirm that all prepared compounds have 1:2 metal-to-ligand stoichiometry except Zn(II) complex, which has 1:1 metal-to-ligand stoichiometry. The antimicrobial activity for complexes was investigated. The antimicrobial activity results revealed that Zn(II) complex (1) has a good potency against gram positive bacteria (E. coli) and gram negative bacteria (P. vulgaris) in comparision with doxymycin standard, AT B3LYP/6-311G (d,p) level, Density Functional Theory (DFT) calculations were carried out to investigate the optimized structure of both, the ligand and the complexes. Total energy, energy of HOMO, and LUMO as well as Mullikan atomic charges were calculated. Dipole moment, orientation, and structure activity relationship were performed and discussed.DFT calculations, moreover, confirmed practical antimicrobial results.
A new dual-channel ratiometric fluorescent chemodosimeter for Cu2+and its imaging in living cells
Fan, Zheng,Ye, Jia-Hai,Bai, Yang,Bian, Song,Wang, Xiaolong,Zhang, Wenchao,He, Weijiang
, p. 5281 - 5285 (2016)
A new BODIPY derivative bearing hydrazone and hydrazide moieties was developed as an efficient dual-channel ratiometric fluorescence chemodosimeter 1 for Cu2+in neutral aqueous medium via Cu2+-mediated hydrolysis of C[dbnd]N bond in hydrazone unit. Confocal microscopy experiments have demonstrated that chemodosimeter 1 could also be used in live cells for the fast detection of Cu2+.
Synthesis and in vitro acetylcholinesterase and butyrylcholinesterase inhibitory potential of hydrazide based Schiff bases
Rahim, Fazal,Ullah, Hayat,Taha, Muhammad,Wadood, Abdul,Javed, Muhammad Tariq,Rehman, Wajid,Nawaz, Mohsan,Ashraf, Muhammad,Ali, Muhammad,Sajid, Muhammad,Ali, Farman,Khan, Muhammad Naseem,Khan, Khalid Mohammed
, p. 30 - 40 (2016)
To discover multifunctional agents for the treatment of Alzheimer's disease, a series of hydrazide based Schiff bases were designed and synthesized based on multitarget-directed strategy. We have synthesized twenty-eight analogs of hydrazide based Schiff bases, characterized by various spectroscopic techniques and evaluated in vitro for acetylcholinesterase and butyrylcholinesterase inhibition. All compounds showed varied degree of acetylcholinesterase and butyrylcholinesterase inhibition when compared with standard Eserine. Among the series, compounds 10, 3 and 24 having IC50 values 4.12?±?0.01, 8.12?±?0.01 and 8.41?±?0.06?μM respectively showed potent acetylcholinesterase inhibition when compared with Eserine (IC50?=?0.85?±?0.0001?μM). Three compounds 13, 24 and 3 having IC50 values 6.51?±?0.01, 9.22?±?0.07 and 37.82?±?0.14?μM respectively showed potent butyrylcholinesterase inhibition by comparing with eserine (IC50?=?0.04?±?0.0001?μM). The remaining compounds also exhibited moderate to weak inhibitory potential. Structure activity relationship has been established. Through molecular docking studies the binding interaction was confirmed.
A Zn(II) luminescent complex with a Schiff base ligand: solution, computational and solid state studies
Martínez, Sebastián,Igoa, Fernando,Carrera, Ignacio,Seoane, Gustavo,Veiga, Nicolás,De Camargo, Andrea S. S.,Kremer, Carlos,Torres, Julia
, p. 874 - 889 (2018)
A new mononuclear complex of zinc(II), [Zn(HL)2]?2DMF (H2L?=?(E)-N′-((E)-(hydroxyimino)butan-2-ylidene)salicyloylhydrazide, DMF?=?N,N-dimethylformamide), was prepared and characterized. Single-crystal X-ray crystallography revealed a six-coordinate zinc(II) surrounded by nitrogen of the oxime function and oxygen and distal nitrogens of the acylhydrazone group. This entity also exists in solution as demonstrated by 1H-NMR and potentiometric titrations. The computational analysis showed that the molecular orbitals involved in the main electronic transitions of the complex species in solution are centered on the ligand with negligible contribution of the metal ion. The photophysical properties of the complex were evaluated in solution and in the solid state. Luminescence studies showed that the solid has a strong emission at 550?nm with a large Stokes shift with respect to absorption. The solid state fluorescence emission is ascribed to ligand-centered and/or ligand-to-ligand charge transfer transitions, following the DFT results in solution. A comparison with a previously reported mononuclear [Zn(HL)2] allowed the investigation of the influence of DMF molecules in the structural packing and the luminescence properties.
Pyrazole derivatives of medically relevant phenolic acids: Insight into antioxidative and anti-lox activity
Bogdanovi?, Goran A.,Brankovi?, Jovica,Milovanovi?, Vesna,Mladenovi?, Milan,Novakovi?, Sla?ana,Petrovi?, Vladimir P.,Petrovi?, Zorica D.,Simijonovi?, Du?ica
, p. 807 - 819 (2021/10/21)
Background: From the point of view of medicinal chemistry, compounds containing phenolic and pyrazolic moiety are significant since they are often constituents of bioactive compounds. Objective: The aims of this study were to synthesize pyrazole derivatives of medically relevant phenolic acids, confirm their structure, and evaluate their antioxidative and anti-LOX activities. Methods: Phenolic pyrazole derivatives were obtained, starting from esters of medically relevant phenolic acids. The structures of all obtained compounds were determined by NMR and IR spectroscopy, and UV-Vis spectrophotometry. In addition, the single-crystal X-ray diffraction was used. Pyrazole derivatives were tested for their in vitro antioxidative (DPPH assay), and lipoxygenase (LOX) inhibitory ac-tivities. Radical quenching mechanism was estimated using DFT and thermodynamic approach, while molecular docking was used to estimate the binding mode within the enzyme. Results: Pyrazole derivatives were obtained in high yields. The crystal structure of a new compound 3e was determined. Pyrazole derivative with catechol moiety 3d exhibited excellent radical scavenging ac-tivity, while compound 3b exhibited the best anti-LOX activity. Molecular docking study revealed that there is no direct interaction of any ligand with the active site of LOX-Ib, but pyrazoles 3a-e behave as inhibitors blocking the approach of linoleic acid to the active site. Conclusion: In this research, protocatechuic and vanillic acid pyrazole derivatives have been obtained for the first time. In vitro antioxidative assay suggests that pyrazole derivate of protocatechuic acid is a powerful radical scavenger, while anti-LOX assay indicates a pyrazole derivative with 4-hydroxyphenyl moiety.
Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction
Zhou, Wenjuan,Xu, Chenhao,Dong, Guanjun,Qiao, Hui,Yang, Jing,Liu, Hongmin,Ding, Lina,Sun, Kai,Zhao, Wen
, (2021/03/24)
Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.
