Structural and molecular docking studies of biologically active mercaptopyrimidine Schiff bases

Kirubavathy, S. Jone; Velmurugan, R.; Karvembu, Ramasamy; Bhuvanesh, Nattamai; Enoch, Israel V.M.V.; Selvakumar, P. Mosae; Premnath, D.; Chitra, S.

doi:10.1016/j.molstruc.2016.07.082

Cited by 39 publications

(11 citation statements)

References 30 publications

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“…So, it is necessary to identify novel, selective, potent and less toxic anticancer agents which became one of the most pressing problems. Cancer is a complex disease that is normally correlated to a wide range of escalating effects both at the cellular and molecular levels . The cytotoxic ability of Schiff base ligand and its metal complexes were evaluated against breast carcinoma cells (MCF‐7 cell line), which is one of the most common form of cancer.…”

Section: Anticancer Activitiesmentioning

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: Anticancer Activitiesmentioning

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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“…They form very easy and coordinate with a large variety of metal ions. This allows using them as catalysts in different reactions and biological systems …”

Section: Introductionmentioning

confidence: 99%

New Chloro‐Based Azo‐Azomethine Dyes: Synthesis, Biological and Optical Spectroscopic Studies for Detection of some Transition Metal Ions

Shaghaghi

Rezanezhad

2018

ChemistrySelect

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Two new chromogenic receptors 1,2-[1-(3-imino-4-hydroxophenylazobenzene)]-4-chlorobenzene (1 a) and 1,2-[1-(3-imino-4hydroxophenylazo-4-nitrobenzene)]-4-chlorobenzene (1 b) have been designed and chearcterized for detection of some transition metal ions in DMSO solution by UV/Vis spectroscopy. Upon addition of Cd 2 + , Zn 2 + and Cu 2 + ions to 1 a in DMSO, the peak at 460 nm increases in intensity, while the band at 352 nm decreases in intensity and approximately disappears. n!p* transition of azo groups of 1 a decreases in intensity after adding Hg 2 + ions and does not change after adding Ni 2 + ions. This indicates high tendency of 1 a towards Cd 2 + , Zn 2 + and Cu 2 + against Ni 2 + and Hg 2 + ions. Compound 1 b shows some color changes after addition of metal ions. Upon addition of all metal ions to 1 b in DMSO, the band at 560 nm increases in intensity with the hypsochromic shift for Cu 2 + , Zn 2 + , Co 2 + and Ni 2 + . But the largest blue shift (-67 nm) is seen after adding Cu 2 + ion with remarkable color change from violet-green to orange. Benesi-Hildebrand plot and Job's method are used for determination of binding constant (K a ) and stoichiometry of formed complexes with 1 b. Then, complex Cu(II) with 1 b is synthezied for recognition of binding sites of ligand. The results indicate that 1 b behaves as one tetradentate ligand with N and O donor atoms when bound to Cu(II). Moreover, the study of antioxidant properties of 1 a and 1 b with DPPH method reveals good and significant activity.[a] Dr.

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“…Schiff base compounds are a class of compounds containing the imine (−C=N−) group, which is formed by the condensation of amine and active carbonyl groups through nucleophilic reaction . Schiff base compounds have a wide range of biological properties, such as antifungal, antibacterial, anticancer, anti‐inflammation, and anticonvulsant activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Activity, and Molecular Docking Studies of Novel 5‐Substituted‐1,2,4‐Triazole‐3‐thione Derivatives

et al. 2020

ChemistrySelect

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Seven Schiff base compounds were synthesized via the nucleophilic condensation of 5‐substituted‐3‐thione‐1,2,4‐triazole and 2,4,6‐trimethyl benzaldehyde. All of the synthesized compounds (A1–A3 and B1–B4) were thoroughly characterized by using spectroscopic and physical analytical methods. The in vitro antifungal activities of the prepared compounds were studied, and results showed that A2, B1, B2, and B3 have good biological activity. Molecular docking was used to predict the binding modes of the ligands to 6CR2 protein, and the reasons behind the excellent activities of A2 and B2 were explored. Finally,the highest occupied molecular orbital, lowest unoccupied molecular orbital, and natural bonding orbital of the compounds were calculated by using density functional theory at the B3LYP/6‐31G level.

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Structural and molecular docking studies of biologically active mercaptopyrimidine Schiff bases

Cited by 39 publications

References 30 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

New Chloro‐Based Azo‐Azomethine Dyes: Synthesis, Biological and Optical Spectroscopic Studies for Detection of some Transition Metal Ions

Synthesis, Biological Activity, and Molecular Docking Studies of Novel 5‐Substituted‐1,2,4‐Triazole‐3‐thione Derivatives

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