Synthesis of Schiff base (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-thiazole-2-yl)benzenesulfonamide with antimicrobial potential, structural features, experimental biological screening and quantum mechanical studies

Elangovan, N.; Thomas, Renjith; Sowrirajan, S.

doi:10.1016/j.molstruc.2021.131762

Cited by 38 publications

(17 citation statements)

References 80 publications

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“… 44 Increasing the softness increases chemical activity, and increasing the hardness decreases the chemical activity. 45 , 46 As determined from the HOMO–LUMO orbital and orbital energy gap ( Tables S6 and S7 , Figures S14 and S15 ), the electron cloud is concentrated on the pyridine ring of the ligand and is composed of the π → π* orbital of C and N. CP- 1 – 4 showed high orbital energy differences of 6.9606, 6.0635, 6.7897, and 7.2436 eV in the HOMO–LUMO orbit, respectively. CP- 4 showed the largest range of orbital energy, and thus, was considered highly stable.…”

Section: Resultsmentioning

confidence: 99%

(8-Hydroxyquinoline) Gallium(III) Complex with High Antineoplastic Efficacy for Treating Colon Cancer via Multiple Mechanisms

et al. 2023

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A series of (8-hydroxyquinoline) gallium(III) complexes (CP-1–4) was synthesized and characterized by single X-ray crystallography and density functional theory (DFT) calculation. The cytotoxicity of the four gallium complexes toward a human nonsmall cell lung cancer cell line (A549), human colon cancer cell line (HCT116), and human normal hepatocyte cell line (LO2) was evaluated using MTT assays. CP-4 exhibited excellent cytotoxicity against HCT116 cancer cells (IC50 = 1.2 ± 0.3 μM) and lower toxicity than cisplatin and oxaliplatin. We also evaluated the anticancer mechanism studies in cell uptake, reactive oxygen species analysis, cell cycle, wound-healing, and Western blotting assays. The results showed that CP-4 affected the expression of DNA-related proteins, which led to the apoptosis of cancer cells. Moreover, molecular docking tests of CP-4 were performed to predict other binding sites and to confirm its higher binding force to disulfide isomerase (PDI) proteins. The emissive properties of CP-4 suggest that this complex can be used for colon cancer diagnosis and treatment, as well as in vivo imaging. These results also provide a foundation for the development of gallium complexes as potent anticancer agents.

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Section: Resultsmentioning

confidence: 99%

(8-Hydroxyquinoline) Gallium(III) Complex with High Antineoplastic Efficacy for Treating Colon Cancer via Multiple Mechanisms

et al. 2023

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“…Titled compound C1 structure was optimized to DFT mode with WB97XD/6‐311 + G(2d,p) basis set level with assistance of Gaussian‐09 package. [ 21‐23 ] Before optimization, conformational analysis was performed and the most stable conformer was selected for the optimization. [ 12 ] The detailed bond angle, bond length and dihedral angles of the optimized structure is tabulated in table S1.…”

Section: Resultsmentioning

confidence: 99%

Quantum mechanical studies of 5‐amino‐2‐(6‐(2‐hydroxyethyl)‐3‐oxononyl) cyclohex‐2‐enone isolated from a marine algae

Begum,

Rao,

Rao

et al. 2022

Vietnam Journal of Chemistry

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The compound C1 from marine algae was isolated and characterized by FTIR, FT‐Raman and UV‐Vis, with compared to experimental and simulated methods. The compound optimized with DFT method with the WB97XD and 6‐311 + G(2d,p) basis set level. The infrared and Raman spectrum were calculated with same basis set level; the simulated spectrum good agreement with experimental one. The HOMO‐LUMO and MEP also calculated with above mentioned same basis set level; this study is mainly predicted to the biological activity of the titled compound C1. The wave function studies like localized orbital locator, electron localized function, average localized ionization energy and non‐covalent interaction also studied for another theoretical evidence of the titled compound. The ADMET properties are also studied for in this compound for the support of Swiss ADMET online tool. Molecular docking study showed a high binding affinity of ‐7.9 kcal/mol to act as a 5‐hydroxytryptamine release stimulant.

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“…In this assay, Mueller Hinton broth and Sabouraud Dextrose agar at pH 7.0 were utilized to culture bacterial and fungi species, respectively [21] . The inocula of tested microorganisms were adjusted to 0.5 McFarland standard turbidity [22] . The final size of inoculum was 1.5×10 4 and 1.5×10 5 cfu/mL for bacteria and fungi species, respectively.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Antimicrobial Evaluation, Molecular Docking, and ADME Studies of Some Novel 3‐Hydroxypyridine‐4‐one Derivatives

Sadeghian,

Zare,

Goshtasbi

et al. 2023

ChemistrySelect

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A new class of 3‐hydroxypyridine‐4‐one derivatives was synthesized and screened against several Gram‐positive and Gram‐negative bacteria, as well as two species of fungi. Among these synthesized compounds, the substituted derivatives with ortho‐ and para‐nitro and para‐methoxy groups showed the highest antibacterial activities against S. aureus and E. coli species with MIC value of 32 μg/mL, which were more potent compared to ampicillin as a reference drug. Furthermore, the substituted derivatives with ortho‐methoxy, ortho‐, para‐chloride, ortho‐, and para‐hydroxy groups exhibited MIC values of 64 μg/mL against S. aureus and E. coli species. In addition, the synthesized compounds were evaluated for their antifungal activities against C. albicans and A. niger strains. The best antifungal activity was observed for compounds with ortho‐methoxy, ortho‐hydroxy, and para‐methyl substitutions against A. niger species with MIC values of 64 μg/mL. The analysis of the antimicrobial results revealed that the type and position of the phenyl ring substituents greatly influence the antimicrobial activities of the synthesized compounds. Subsequently, molecular docking studies on E. coli species were performed to predict the interaction mode of these compounds in the active site of the receptor. Also, in silico ADME profile outputs showed that the compounds comply with the rule of five.

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Synthesis of Schiff base (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-thiazole-2-yl)benzenesulfonamide with antimicrobial potential, structural features, experimental biological screening and quantum mechanical studies

Cited by 38 publications

References 80 publications

(8-Hydroxyquinoline) Gallium(III) Complex with High Antineoplastic Efficacy for Treating Colon Cancer via Multiple Mechanisms

(8-Hydroxyquinoline) Gallium(III) Complex with High Antineoplastic Efficacy for Treating Colon Cancer via Multiple Mechanisms

Quantum mechanical studies of 5‐amino‐2‐(6‐(2‐hydroxyethyl)‐3‐oxononyl) cyclohex‐2‐enone isolated from a marine algae

Synthesis, Antimicrobial Evaluation, Molecular Docking, and ADME Studies of Some Novel 3‐Hydroxypyridine‐4‐one Derivatives

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