Serkan Dayan

Experimental and molecular modeling investigation of (E)-N-{2-[(2-hydroxybenzylidene)amino]phenyl}benzenesulfonamide

The Schiff base compound (E)-N-{2-[(2-hydroxybenzylidene)amino]phenyl}benzenesulfonamide has been synthesized and characterized by IR, NMR and Uv-vis spectroscopies, and single-crystal X-ray diffraction technique. In addition, quantum chemical calculations employing density functional theory (DFT) method with the 6–311++G(d,p) basis set were performed to study the molecular, spectroscopic and some electronic structure properties of the title compound, and the results were compared with the experimental findings. There exists a good correlation between experimental and theoretical data. Enol-imine/keto-amine tautomerization mechanism was investigated in the gas phase and in solution phase using the polarizable continuum model (PCM) approximation. The energetic and thermodynamic parameters of the enol-imine → keto-amine transfer process show that the single proton exchange is thermodynamically unfavored both in the gas phase and in solution phase. However, the reverse reaction seems to be feasible with a low barrier height and is supported by negative values in enthalpy and free energy changes both in the gas phase and in solution phase. The solvent effect is found to be sizable with increasing polarity of the solvents for the reverse reaction. The predicted nonlinear optical properties of the compound are found to be much greater than those of urea.

Synthesis and pro-apoptotic effects of new sulfonamide derivatives via activating p38/ERK phosphorylation in cancer cells

Abstract Herein, the compounds bearing sulfonamide fragment such as N-(2-amino-5-benzoylphenyl)-4-nitrobenzene sulfonamide hydrochloride (1), N-(quinolin-8-yl)-4-nitro-benzenesulfonamide hydrochloride (2), N-(pyridine-2-ylmethyl)-4-nitro-benzenesulfonamide hydrochloride (3) were synthesized by the reaction of 3,4-diaminobenzophenone, 8-aminoquinoline or 2-picoylamine and 4-nitrobenzensulfonyl chloride, respectively. The structures of the newly synthesized compounds were elucidated on the basis of elemental and spectral analyses. All the prepared compounds were evaluated for their in vitro anti-cancer activity against various cancer cell lines and to explore the underlying molecular mechanisms involved in this process. In vitro cytotoxic activities of the compounds were screened against human hepatocellular (HepG2), breast (MCF-7) and colon (Colo-205) cancer cell lines by MTT assay, mRNA expression of genes with qPCR and phosphorylation of p38 and ERK1/2 with Western blot. Tested compounds could significantly reduce cell proliferation and induced mRNA expression of pro-apoptotic genes; caspase 3, caspase 8 and caspase 9. Activation of these apoptotic genes probably is mediated by activation of p38.

Synthesis of imine and reduced imine compounds containing aromatic sulfonamide: Use as catalyst for in situ generation of ruthenium catalysts in transfer hydrogenation of acetophenone derivatives

Three imine and three reduced imine ligands containing aromatic sulfonamide (2-7) were isolated by a simple method and characterized by FT-IR, NMR, and elemental analysis. Meanwhile, the interaction of 2-7 ligands with [(p-cymene)RuCl2]2 was analyzed in situ by UV-vis spectrophotometer. The in situ generated catalytic system derived from N-(2-(benzylideneamino)phenyl)-2,4,6-trimethyl-benzenesulfonamides and N-(2-(benzylamino)phenyl)-2,4,6-trimethyl-benzenesulfonamides with [(p-cymene)RuCl2]2 was used as a catalyst in the transfer hydrogenation (TH) of p-substituted acetophenone derivatives. The catalytic systems displayed high activities, which increased in the order 7<4<5<6<1<2<3. The best activity for the TH of 4-chloroacetophenone was provided with the [(p-cymene)RuCl2]2/ligand (3) catalytic system (turnover frequency values: 720 h(-1) for 10 min on S/C: 500/1).

Potential anti-inflammatory effect of water-soluble sulfonamido compounds on lipopolysaccharide-stimulated macrophage-like cellular systems

The present study was designed to investigate the potential anti-inflammatory effects and mechanisms of water-soluble sulfonamido compounds such as Sodium-N-(2-amino-5-benzoylphenyl)-4-n-propyl-benzenesulfonamido (1), Sodium-N-(2-amino-5-benzoylphenyl)-2,4,6-trimethyl-benzenesulfonamido (2), Sodium-N-(2-amino-5-benzoylphenyl)-4-chloro-benzenesulfonamido (3) and Sodium-N-(2-amino-5-benzoylphenyl)-4-methoxy-benzenesulfonamido (4) in Raw 267.4 macrophages and BV-2 microglia cells. Compounds (1–4) identities are characterized by various methods such as 1H-NMR, 13C-NMR, FT-IR, UV–Vis, cyclic voltammetry and elemental analysis. Cytotoxicity (MTT method) and production of cytokines were determined with ELISA. Furthermore, intracellular mitogen-activated protein kinase (MAPK) signaling pathway and cyclooxygenase-2 (Cox-2) expression were analyzed by Western blot. Lowest cytotoxicity was seen in compound 4 treated cells. The compound 4 inhibited lipopolysaccharide-stimulated Cox-2 expression and p38/ERK MAPK pathway in both cell lines. In addition, the inhibitory action of compound 4 not only restricted Cox-2 and p38/ERK MAPKs, but also inhibited the secretion of pro-inflammatory cytokines TNF-α/IL-6 and activated anti-inflammatory cytokine IL-10. The experimental results suggest the anti-inflammatory action of water-soluble sulfonamido compounds on activated macrophage-like cellular systems, which could be used as a future therapeutic agent in the management of chronic inflammatory diseases.

Fabrication of MgAl2Si2O8 : M0.01 (M = Ni2+, Cu2+, Pd2+, Pt2+ and Ru3+): catalytic effects for the reduction of 2- or 4-nitroanilines in water

Five new MgAl2Si2O8 : M0.01 (M = Ni2+, Cu2+, Pd2+, Pt2+ and Ru3+) materials were developed for the reduction of nitroarenes as catalysts by conventional solid state reaction at 1300∘C. The prepared materials were characterized by thermal analysis, Fourier transform infrared spectroscopy, X-ray powder diffraction analysis, scanning electron microscopy, energy-dispersive X-ray analysis and nitrogen adsorption–desorption analysis. The catalytic activities of the prepared catalysts were tested in the reduction of 2- or 4-nitroanilines in aqueous media at ambient temperature in the presence of NaBH4 by UV–vis spectrophotometer. Furthermore, the MgAl2Si2O8 : M0.01 catalysts can be recovered by filtration and reused for five cycles for the reduction of 2-nitroaniline. These results show that the MgAl2Si2O8 : M0.01 catalysts can be used in practical applications in the reduction of nitroanilines.