Synthesis, structure, antibacterial studies and DFT calculations of arene ruthenium, Cp∗Rh, Cp∗Ir and tricarbonylrhenium metal complexes containing 2-chloro-3-(3-(2-pyridyl)pyrazolyl)quinoxaline ligand

Sangilipandi, S.; Sutradhar, Dipankar; Bhattacharjee, Kaushik; Kaminsky, Werner; Joshi, S. R.; Chandra, Asit K.; Rao, Kollipara Mohan

doi:10.1016/j.ica.2015.11.012

Cited by 36 publications

(16 citation statements)

References 76 publications

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“…Examples of (1H-pyrazol-1-yl)pyrazine coordinated to transition metal have been previously described (2,3). Bis-pyrazolylpyrazine derivatives coordinated to a transition metal ion have been described (4)(5)(6)(7)(8)(9)(10)(11), although this includes, to the best of our knowledge, no example of the 2,5 substitutions.…”

Section: Introductionmentioning

confidence: 99%

The Effect of Pyrazolyl Substituents on the Photophysical and Photochemical Properties of Pyrazine Derivatives

Pizarro

Prado

Saldías

et al. 2018

Photochem & Photobiology

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The reaction of 2,5-dibromopyrazine with N-Lithium pyrazolate in a 1:2 ratio leads to a mixture of 2-bromo-5-(1H-pyrazol-1-yl)pyrazine (I) and 2,5-di(1H-pyrazol-1-yl)pyrazine (II). The structures of I and II are highly planar. Two absorption bands can be observed for the compounds in the UV-Vis region, having ε in the order of 10 m cm . TD-DFT computed results support the nature of the lower energy absorptions as π →π* transitions, including an additional intraligand charge transfer transition for I (π →π* ). Upon excitation at 280 or 320 nm, the emission of both compounds is almost not affected by solvent polarity or oxygen presence, showing two bands for I and one for II in the 350-450 nm region. Emission of II follows a mono-exponential decay, while I decays following a bi-exponential law, hypothesized from π →π* and π →π* transitions. Photodegradation of I and II follows a first-order kinetic with constants of 1.18 × 10 min and 0.13 × 10 min , respectively. Results suggest that photodegradation of I starts with the loose of bromide followed by intermolecular pyrazolyl subtraction and ring opening. This path is not available for II, which is reflected in its enhanced photostability.

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Section: Introductionmentioning

confidence: 99%

The Effect of Pyrazolyl Substituents on the Photophysical and Photochemical Properties of Pyrazine Derivatives

Pizarro

Prado

Saldías

et al. 2018

Photochem & Photobiology

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“…The electronic structure calculation of the HL ligand was carried out using the Gaussian03 suite of program . They were fully optimized employing the density functional theory (DFT)‐based B3LYP method along with the LAN12DZ basis set.…”

Section: Methodsmentioning

confidence: 99%

Physicochemical characterization of nanobidentate ferrocene‐based Schiff base ligand and its coordination complexes: Antimicrobial, anticancer, density functional theory, and molecular operating environment studies

Mahmoud

2019

J Chinese Chemical Soc

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A novel bidentate Schiff base ligand (HL, Nanobidentate Ferrocene based Schiff base ligand L (has one replaceable proton H)) was prepared via the condensation of 2‐amino phenol with 2‐acetyl ferrocene. The ligand was characterized using elemental analysis, mass spectrometry, infrared (IR) spectroscopy, 1proton nuclear magnetic resonance (H‐NMR) spectroscopy, scanning electron microscopy (SEM), and thermal analysis. The corresponding 1:1 metal complexes with some transition‐metal ions were additionally characterized by their elemental analysis, molar conductance, SEM, and thermogravimetric ana1ysis (TGA). The complexes had the general formula [M(L)(Cl)(H2O)3]xCl·nH2O (M = Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II)), (x = 0 for Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II), x = 1 for Cr(III) and Fe(III)), (n = 1 for Cr(III), n = 3 for Mn(II) and Co(II), n = 4 for Fe(III), Ni(II), Cu(II), Zn(II), and Cd(II)). Density functional theory calculations on the HL ligand were also carried out in order to clarify molecular structures by the B31YP exchange‐correlation function. The results were subjected to molecular orbital diagram, highest occupied mo1ecu1ar orbital–lowest occupied molecular orbital, and molecular electrostatic potential calculations. The parent Schiff base and its eight metal complexes were assayed against four bacterial species (two Gram‐negative and two‐Gram positive) and four different antifungal species. The HL ligand was docked using molecular operating environment 2008 with crystal structures of oxidoreductase (1CX2), protein phosphatase of the fungus Candida albicans (5JPE), Gram(−) bacteria Escherichia coli (3T88), Gram(+) bacteria Staphylococcus aureus (3Q8U), and an androgen‐independent receptor of prostate cancer (1GS4). In order to assess cytotoxic nature of the prepared HL ligand and its complexes, the compounds were screened against the Michigan cancer foundation (MCF)‐7 breast cancer cell line, and the IC50 values of compounds were calculated.

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“…The electronic structure calculation for the free ligand was carried out using the Gaussian03 suite of programs . The structures were fully optimized employing the DFT‐based B3LYP method along with the LANL2DZ basis set.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, characterization, spectroscopic and theoretical studies of transition metal complexes of new nano Schiff base derived from l‐histidine and 2‐acetylferrocene and evaluation of biological and anticancer activities

Mahmoud

Omar

Sayed

2018

Applied Organom Chemis

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A new Schiff base derived from the condensation of 2‐acetylferrocene with l‐histidine was prepared and characterized using elemental analyses and spectroscopic methods. Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) complexes of the Schiff base were prepared and characterized using various physicochemical methods such as elemental analysis, Fourier transform infrared and UV–visible spectroscopies, molar conductance, thermal analysis and scanning electron microscopy (SEM). Both ligand and complexes were investigated for their biological and anticancer activities. The elemental analyses showed that complexes were formed in a metal‐to‐ligand ratio of 1:1 stoichiometry. The spectral analyses proved that the ligand was tridentate and all complexes had an octahedral geometry, except the Zn(II) complex that was tetrahedral. SEM showed that the ligand and its Cd(II) complex were of nanometric structure. The molecular and electronic structure of the free ligand was optimized theoretically and the quantum chemical parameters were calculated. The molecular structure can be used to investigate the coordination sites and the total charge density around each atom. According to anticancer studies, Cd(II) complex was recommended to be used as anti‐breast cancer drug as it had very low IC50 (3.5 μg ml−1). Molecular docking was used to predict the binding between the free ligand and its Cd(II) complex and crystal structure of Staphylococcus aureus (PDB ID: 3Q8u), receptors of breast cancer mutant oxidoreductase (PDB ID: 3Hb5) and crystal structure of Escherichia coli (PDB ID: 3 T88) and to identify the binding mode and the crucial functional groups interacting with the three proteins.

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Synthesis, structure, antibacterial studies and DFT calculations of arene ruthenium, Cp∗Rh, Cp∗Ir and tricarbonylrhenium metal complexes containing 2-chloro-3-(3-(2-pyridyl)pyrazolyl)quinoxaline ligand

Cited by 36 publications

References 76 publications

The Effect of Pyrazolyl Substituents on the Photophysical and Photochemical Properties of Pyrazine Derivatives

The Effect of Pyrazolyl Substituents on the Photophysical and Photochemical Properties of Pyrazine Derivatives

Physicochemical characterization of nanobidentate ferrocene‐based Schiff base ligand and its coordination complexes: Antimicrobial, anticancer, density functional theory, and molecular operating environment studies

Synthesis, characterization, spectroscopic and theoretical studies of transition metal complexes of new nano Schiff base derived from l‐histidine and 2‐acetylferrocene and evaluation of biological and anticancer activities

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