Synthesis, spectroscopy, X-ray crystallography, DFT calculations, DNA binding and molecular docking of a propargyl arms containing Schiff base

Balakrishnan, Chithiraivel; Subha, L.; Neelakantan, M.A.; Mariappan, S.S.

doi:10.1016/j.saa.2015.06.013

Cited by 32 publications

(14 citation statements)

References 38 publications

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“…It necessitates the ligand and the receptor as PDB format input. The water molecules, co‐crystallized ligands and other unsupported elements (e.g., Na, K, Hg, etc.,) were removed but the amino acid chain was kept . The structure of the ligand in PDB file format was created by Gaussian03 software.…”

Section: Methodsmentioning

confidence: 99%

Metal complexes of novel Schiff base derived from iron sandwiched organometallic and 4‐nitro‐1,2‐phenylenediamine: Synthesis, characterization, DFT studies, antimicrobial activities and molecular docking

Mahmoud

Deghadi

2018

Applied Organom Chemis

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The condensation of 2-acetylferrocene with 4-nitro-1,2-phenylenediamine in a 1:1 molar ratio, resulting in formation of a novel bi-dentate organometallic Schiff base ligand (L), (2-(1-((2-amino-5-nitrophenyl)imino)ethyl)cyclopenta-2,4-dien-1-yl)(cyclopenta-2,4-dien-1-yl)iron. Also, its Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) complexes have been synthesized. The stoichiometric ratios of the prepared compounds were estimated using elemental analysis (C, H, N, M), molar conductivity, FT-IR, UV-Vis, 1 H-NMR, SEM and mass spectral analysis. Furthermore, their TG and DTG properties were studied. The geometrical structure of the complexes was found to be octahedral. From spectral analysis, the Schiff base coordinated to metal ions through the azomethine and amine groups. DFT-based molecular orbital energy calculations of the synthesized ligand have been studied, in which the ligand was theoretically optimized.The Schiff base and its metal complexes have been screened for their antimicrobial activities against different bacterial and fungal species by using disc diffusion method. The anticancer activities of the ligand and its metal complexes have also been studied towards breast cancer (MCF-7) and human normal melanocytes (HFB-4) cell lines. Molecular docking was also used to identify the interaction between the Schiff base ligand and its Cd(II) complex with the active site of the receptors of breast cancer mutant oxidoreductase (PDB ID: 3HB5), crystal structure of Staphylococcus aureus (PDB ID: 3Q8U) and yeast-specific serine/threonine protein phosphatase (PPZ1) of Candida albicans (PDB ID:5JPE).

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Section: Methodsmentioning

confidence: 99%

Metal complexes of novel Schiff base derived from iron sandwiched organometallic and 4‐nitro‐1,2‐phenylenediamine: Synthesis, characterization, DFT studies, antimicrobial activities and molecular docking

Mahmoud

Deghadi

2018

Applied Organom Chemis

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“…Tables S2 and S3, in the Supporting Information, show the experimental and theoretical vibrational frequencies and their respective assignment for I and II , respectively. The analysis includes also a vibrational band assignment based on the computed Potential Energy Distribution (PED) analysis and comparison with reported data available in the literature for similar molecules …”

Section: Resultsmentioning

confidence: 99%

“…The molecular structures of aryl propargyl ethers in the crystalline phase show that the terminal propargyl group is rather acidic, allowing for the formation of hydrogen bonds (–C≡C–H⋅⋅⋅A) . Moreover, hybrid compounds bearing the propargyl ether moiety and chromen‐2‐one, and Schiff base showed salient spectroscopic properties attributed to the acidic acetylene end group.…”

Section: Introductionmentioning

confidence: 99%

Interplay between Conformation and Crystal Packing in Aryl Propargyl Ethers: Structural and Spectroscopic Properties of 2‐(prop‐2‐yn‐1‐yloxy)acene Derivatives

et al. 2019

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The 2-(prop-2-yn-1-yloxy)naphthalene (compound I) and 1nitro-2-(prop-2-yn-1-yloxy)benzene (compound II) were prepared in excellent yields by the reaction of propargyl bromide with 2-naphthol and 2-nitrophenol, respectively. Structural and conformational properties of both compounds have been analyzed using a combined approach including single-crystal X-ray diffraction and quantum chemical calculations. Two forms are found to be stable and nearly isoenergetic conformers, depending on the mutual orientation of the C � C triple bond and the O-C single bond of the prop-2-yn-1-yloxy group. The gauche conformation is the most stable form for the vacuum isolated species, with the anti conformation higher in energy by 1.00 and 1.89 kcal/mol computed at the M06-2X/6-311 + + G(d,p) level of approximation, for I and II, respectively. The gauche form is observed in the crystal of I but the nearly planar anti conformation is adopted in the crystalline phase of compound II. The occurrence of C-H⋅⋅⋅π and C-H⋅⋅⋅O intermolecular interactions involving the acidic -C � C-H hydrogen donor and -C � C-and -OCH 2 -acceptors is discussed. Furthermore, vibrational features of the prop-2-yn-1-yloxy moiety are analyzed by infrared and Raman spectroscopy. The UV-Vis spectrum shows the presence of well-defined absorption at ca. 280 and 320 nm assigned to the π!π* transitions in the naphtyl/benzyl and prop-2-yn-1-yloxy groups, respectively.

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Section: Introductionmentioning

confidence: 99%

“…Theoretical NMR calculations and their comparisons with experimental NMR values are as important as the experimental characterization methods and constitute one of supportive methods of characterization generally referred to by scientists in recent studies [33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49] In this study, four optically active Schiff bases, which are well known [50][51][52][53] but no theoretical studies or enzyme inhibition/activation studies were conducted, were synthesized and their inhibition and activation effects on human CA I and II enzymes were investigated. In addition, each compound was optimized by the density functional theory (DFT) method and B3LYP/6-311+G(2d,p) basis set using Gaussian 09 [54] software package, and theoretical 1 H NMR shift values were calculated.…”

Section: Introductionmentioning

confidence: 99%

Investigation of the Effect of Some Optically Active Imine Compounds on the Enzyme Activities of hCA‐I and hCA‐II under In Vitro Conditions: An Experimental and Theoretical Study

Tektas

Akkemik

Baykara

2016

J Biochem & Molecular Tox

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Inhibitors of carbonic anhydrase (hCA; EC 4.2.1.1) are used as medicines for many diseases. Therefore, they are very important. In this study, a known series of Schiff bases were synthesized and their effects on the activities of hCA-I and hCA-II, which are cytosolic isoenzymes of carbonic anhydrase, were investigated under in vitro conditions. The synthesized compounds (H1, H2, H3, and H4) were found to cause inhibition on enzyme activities of hCA-1 and hCA-II. IC50 values of H1, H2, H3, and H4 compounds were 140, 88, 201, and 271 μM for hCA-I enzyme activity and 134, 251, 79, and 604 μM for hCA-II enzyme activity, respectively. The synthesized Schiff bases were characterized by several methods, including (1) H NMR, FT-IR, elemental analysis, and polarimetric measurements. Correlation coefficient square values (R(2) ) of comparison of the theoretical and experimental (1) H NMR shifts for H1, H2, H3, and H4 compounds were found as 0.9781, 0.9814, 0.9758, and 0.8635, respectively.

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Synthesis, spectroscopy, X-ray crystallography, DFT calculations, DNA binding and molecular docking of a propargyl arms containing Schiff base

Cited by 32 publications

References 38 publications

Metal complexes of novel Schiff base derived from iron sandwiched organometallic and 4‐nitro‐1,2‐phenylenediamine: Synthesis, characterization, DFT studies, antimicrobial activities and molecular docking

Metal complexes of novel Schiff base derived from iron sandwiched organometallic and 4‐nitro‐1,2‐phenylenediamine: Synthesis, characterization, DFT studies, antimicrobial activities and molecular docking

Interplay between Conformation and Crystal Packing in Aryl Propargyl Ethers: Structural and Spectroscopic Properties of 2‐(prop‐2‐yn‐1‐yloxy)acene Derivatives

Investigation of the Effect of Some Optically Active Imine Compounds on the Enzyme Activities of hCA‐I and hCA‐II under In Vitro Conditions: An Experimental and Theoretical Study

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