140-87-4Relevant academic research and scientific papers
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.
Green Synthesis of Pyrazole and Oxazole Derivatives
Toche, Raghunath B.,Patil, Vasant M.,Chaudhari (Patil), Sunita A.,Chavan, Satish M.,Sabnis, Ram W.
, p. 38 - 43 (2019)
New intermediate 3-methyl-5-oxopyrazol propanenitrile was synthesized by one pot three component reactions using ethyl cyanoacetate, hydrazine hydrate, and ethyl acetoacetate and was used for the synthesis of new oxazole and pyrazole derivatives. All reactions were carried out using eco-friendly solvents and without catalyst.
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.
Synthesis, characterization and DNA photocleavage study of a novel dehydroacetic acid based hydrazone Schiff's base and its metal complexes
Pal,Kumar,Gupta,Beniwal
, p. 3327 - 3335 (2014)
A series of some novel colored complexes of Co(II), Ni(II), Cu(II), Mn(II) and Zn(II) with a novel dehydroacetic acid based hydrazone Schiff's base has been synthesized and evaluated for their DNA photocleavage potential. The ligand utilized in the present investigation was synthesized via a condensation reaction between cyanoacetic acid hydrazide and dehydroacetic acid. Further, the ligand was treated with different metal acetates of first transition series in 1:1 and 1:2 (metal to ligand) ratios, respectively, to obtain metal complexes with different ligand to metal stoichiometry. Ligand as well as all the synthesized metal complexes were characterized on the basis of data obtained from the techniques like 1H and 13C NMR, IR spectroscopy, mass spectrometry, UV visible spectroscopy, elemental analysis and molar conductance. 1H NMR spectrum of Zn(II) complexes showed the coordination of enolic oxygen atom without deprotonation, but in case of DLCu, the deprotonation of enolic proton was occurred prior to coordination. IR data revealed the participation of a carbonyl oxygen atom of ligand in coordination with metal ions. UV visible data confirmed the square-planar and octahedral geometry of the complexes. Mass spectrum showed the formation of both 1:1 and 1:2 metals to ligand stoichiometry. Most of metal complexes exhibited very good DNA photocleavage activities.
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.
Synthesis of Diphenyl Pyridazinone-based flexible system for conformational studies through weak noncovalent interactions: Application in DNA binding
Kumar, Ranjeet,Singh, Praveen,Gaurav, Archana,Yadav, Pratima,Khanna, Ranjana S.,Tewari, Ashish Kumar
, p. 555 - 564 (2016)
This paper reports conformational studies of pyridazinone-based flexible dimer connected through diethylamine linker. The conformational studies have been done by X-ray crystal structure and DFT calculation. Further, after crystallization, the compound has shown two types of crystals, one is hydrated and another one is non-hydrated. The hydrated and non-hydrated crystals showed difference in their conformation due to the presence of water in crystal lattice of hydrated crystal. The difference in their conformation has been proved by crystallographic studies, DSC curves and detailed analysis of Hirshfeld surfaces and fingerprint plots facilitating a comparison of intermolecular interactions. Along with conformational studies, this compound also showed DNA binding, as revealed in docking simulation studies.
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.
2-Imino 2H-chromene and 2-(phenylimino) 2H-chromene 3-aryl carboxamide derivatives as novel cytotoxic agents: synthesis, biological assay, and molecular docking study
Edraki, Najmeh,Iraji, Aida,Firuzi, Omidreza,Fattahi, Yousef,Mahdavi, Mohammad,Foroumadi, Alireza,Khoshneviszadeh, Mehdi,Shafiee, Abbas,Miri, Ramin
, p. 2163 - 2171 (2016)
The inhibition of AKR1B10 has been recognized as a potential therapeutic approach to the treatment of various types of cancers. A novel series of compounds with imino-2H-chromen and phenylimino-2H-chromen scaffolds were synthesized by Knoevenagel condensation reaction. The in vitro cytotoxic activity of synthesized compounds was evaluated against MOLT-4 and SK-OV-3 cells. Among the tested compounds, N-(3,4-dimethoxyphenyl)-2-(phenylimino)-2H-chromene-3-carboxamide (8g) demonstrated potent inhibitory activity against both examined cell lines. The results of the molecular docking study suggested that this compound is involved in critical hydrogen-bonding interactions with the Val301 and Lue302 of AKR1B10 catalytic site.
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.
AIE based “on-off” fluorescence probe for the detection of Cu2+ ions in aqueous media
Assiri, Mohammed A.,Al-Sehemi, Abdullah G.,Pannipara, Mehboobali
, p. 11 - 15 (2018/11/20)
A simple hydrazine carboxamide derivative with intramolecular charge transfer and aggregation induced emission (AIE) properties have been designed and synthesized. The derivative (Probe 1) shows typical AIE characteristic emission in THF-water mixtures and emits yellowish orange color on reaching the water fraction 98%. The probe molecule show selective sensing response for Cu2+ ions via fluorescence turn-off mechanism in aqueous media over other metal ions. The emission changes towards Cu2+ ions that could be clearly observed by the naked eyes under 365 nm UV lamp promote the probe molecule as a promising candidate for practical utilization. Furthermore, from the fluorescence titration data, the detection limit for Cu2+ ions was found to be 0.44 μM.
