140-87-4Relevant articles and documents
Synthesis, spectral, magnetic, DFT calculations, antimicrobial studies and phenoxazinone synthase biomimetic catalytic activity of new binary and ternary Cu(II), Ni(II) and Co(II) complexes of a tridentate ONO hydrazone ligand
Shebl, Magdy,Saleh, Akila A.,Khalil, Saied M. E.,Dawy, Magdah,Ali, Amira A. M.
, p. 195 - 209 (2021)
New mononuclear copper(II), nickel(II) and cobalt(II) hydrazone complexes of 2-cyano-N′-((4-oxo-4H-chromen-3-yl)methylene)acetohydrazide have been synthesized. Structure identification of the prepared complexes was carried out by physicochemical and spectroscopic techniques including elemental analyses, infrared, electronic, mass and electron spin resonance spectra, thermal analysis, conductivity and magnetic susceptibility measurements, powder x-ray diffraction and transmission electron microscope. The isolated binary complexes are neutral mononuclear complexes (with 1:1 and 1:2; M:L stoichiometries) and ternary complexes (with 1:1:1; M:L:L′ stoichiometry). The analytical and spectroscopic techniques illustrated the monoanionic tridentate behavior of the hydrazone ligand with γ-pyrone oxygen, enolic oxygen and azomethine nitrogen coordinating sites. The metal complexes displayed square planar, tetrahedral and octahedral geometries. Density Functional Theory calculations were carried out for the chelating agent and its copper(II) chelates. The phenoxazinone synthase activity of the binary copper(II) complexes was studied and discussed. The antimicrobial activity of the hydrazone ligand and its complexes was evaluated toward some sorts of Gram–positive bacteria, Gram–negative bacteria, yeast and fungus.
Ring-chain transformation of 4-aroyl-5-phenylamino-2,3-dihydrothiophene-2,3-diones: Facile and efficient synthesis of novel pyrrolo[2,3-c]pyrazol-3(2H)-ones and 1,2-dihydro-5H,6H-pyridazine-5,6-diones
Hafez Taghva, Pardis,Kabirifard, Hassan
, p. 200 - 209 (2020)
Seven, novel pyrrolo[2,3-c]pyrazol-3(2H)-one and 1,2-dihydro-5H,6H-pyridazine-5,6-dione chromophores were synthesized by the reaction of 4-aroyl-5-phenylamino-2,3-dihydrothiophene-2,3-diones with cyanoacetohydrazide and arylhydrazines such as phenylhydrazine and 4-nitrophenylhydrazine. These derivatives were characterized by elemental analysis, IR, UV-Visible, 1H, 13C NMR and mass spectroscopy. Spectral characteristics of the compounds were studied in four organic solvents of differing polarity.
Multifunctional iminochromene-2H-carboxamide derivatives containing different aminomethylene triazole with BACE1 inhibitory, neuroprotective and metal chelating properties targeting Alzheimer's disease
Iraji, Aida,Firuzi, Omidreza,Khoshneviszadeh, Mehdi,Tavakkoli, Marjan,Mahdavi, Mohammad,Nadri, Hamid,Edraki, Najmeh,Miri, Ramin
, p. 690 - 702 (2017)
Alzheimer's disease (AD) is a neurodegenerative disorder known for the presence of amyloid beta plaques resulting from the sequential action of β-secretase and γ-secretase on amyloid precursor protein. We developed and synthesized, through click reactions, a new family of iminochromene carboxamides containing different aminomethylene triazole. The BACE1 inhibition, neuroprotective capacity and metal chelation of these derivatives make them ideal candidates against AD. Most of the synthesized compounds were shown to have potent BACE1 inhibitory activity in a FRET assay, with an IC50 value of 2.2 μM for the most potent compound. Moreover, molecular modeling evaluation of these BACE1 inhibitors demonstrates the vital role of the amine and amide linkers through hydrogen bond interactions with key amino acids in the BACE1 active site. Our in vitro neuroprotective evaluations in PC12 neuronal cells of Aβ-induced neuroprotection demonstrated promising activity for most of the compounds as neuroprotective agents. Based on our findings, we propose that introduction of a phthalimide substitute on the triazole ring shown to be interesting multifunctional lead compound worthy of further study.
A new modification of the Friedlaender synthesis. A simple route to 2-aminoquinoline-3-carboxylic acid and its derivatives
Ukhin,Belov
, p. 418 - 421 (2008)
A new version of the Friedlaender synthesis of 2-aminoquinoline-3- carboxylic acid and its derivatives from stable 2-tosylaminobenzaldehyde or its morpholinal was proposed.
Spectroscopic characterization of Cu(II), Ni(II), Co(II) complexes, and nano copper complex bearing a new S, O, N-donor chelating ligand. 3D modeling studies, antimicrobial, antitumor, and catalytic activities
Ali, Amira A. M.,Dawy, Magdah,El-ghamry, Mosad A.,Khalil, Saied M. E.,Saleh, Akila A.,Shebl, Magdy
, (2021/10/12)
A new tridentate hydrazone ligand (HL), its Co(II), Ni(II), Cu(II) complexes (in 1:1, 1:2 molar ratios of metal to ligand), and the mixed-ligand Co(II), Ni(II), Cu(II) complexes of the ligand HL, with 8-HQ in 1:1:1 (M:L:8-HQ) stoichiometry, in addition to a nano Cu(II) complex have been synthesized and characterized using physical, analytical and spectral methods. Octahedral geometry was assigned for all investigated complexes except Cu(II) complex 1 which exhibited square planar arrangement. The TGA results suggested the thermal stability of the current complexes. The XRD data indicated that the particles of Cu(II) complex 2 were situated in nano-scale range. Furthemore, the SEM and TEM images of the nano Cu(II) complex 2 showed spherical and sheet-shaped particles with an average size of 48 nm. The geometries of the metal complexes were optimized with respect to the energy taking the 6-311G(p,d) basis set in Gaussian 09 W program in gaseous phase by DFT. The data obtained revealed that all metal complexes are more reactive than the free ligand HL, and the Cu(II) complex 1 has the highest chemical reactivity. The antimicrobial activity study illustrated enhancement in activity of the free ligand upon complex formation., and the Cu(II) complex 1 may be considered as promising antibacterial agent, and as promising antifungal agent. The results of antitumor activity study revealed an inhibition of HepG-2 cell growth for the ligand HL, with enhancement in activity upon complexation, and the Cu(II) complex 1 exhibited the highest cytotoxic activity. The phenoxazinone synthase activity study indicated the ability of both Cu(II) complexes 1 and 2 to catalyze the oxidative dehydrogenation of 2-aminophenol (OAPH) to 2-aminophenoxazine-3-one (APX) under atmospheric conditions and at room temperature.
