Zinc(II) Complexes of Acetophenone and 5-Chloro-2-hydroxy-benzophenone Thiosemicarbazones. Synthesis, Characterization, and Nonlinear Optical Properties from Quantum Chemical Calculations

A number of mixed ligand complexes of zinc(II) with acetylacetone, acetophenone thiosemicarbazone, and 5-chloro-2-hydroxy-benzophenone thiosemicarbazone ligands were synthesized. The complexes [Zn(L)(acac)(2)] were characterized by elemental analysis as well as by IR and H-1 NMR spectroscopy. The structure of the zinc(II) complex of acetophenone thiosemicarbazone (1) was determined by single crystal X-ray diffraction. Complex 1 crystallizes in the monoclinic space group P21/c with Z = 4. In vacuo geometry optimization and electronic calculation have been performed using Density Functional Theory (DFT) without any symmetry constraints for the compounds. Experimental and calculated data indicated that the thiosemicarbazone ligand acts as monodentate ligand through the sulphur atom and the complex adopts distorted square-pyramidal geometry, which consists of the sulphur atom and four oxygen atoms of the acetylacetone moieties. Polarizability (alpha), first hyperpolarizability (beta), frontier orbital energies, and dipole moment (mu) are also reported for ligands L-1, L-2, and complexes 1 and 2

Cytotoxic, genotoxic and apoptotic effects of naringenin-oxime relative to naringenin on normal and cancer cell lines

Objective: To assess and compare the cytotoxic, genotoxic, apoptotic and reactive oxygen species (ROS) generating effects of naringenin (NG) and its new derived compound naringenin-oxime (NG-Ox) on MCF-7, HT-29, PC-12 cancer and L-929 normal cell lines. Methods: The cells were incubated with different doses of NG-Ox and NG (50–1000 μmol/L) for 24 h. The cell viability was assessed based on ATP cell viability assay. Intracellular accumulation of ROS was determined using the fluorescent probes 2′7′-dichlorodihydrofluorescin diacetate. Genotoxic effects were evaluated by alkaline single cell gel electrophoresis assay (comet assay) and, the apoptotic effect was evaluated by acridine orange staining at below the IC50 levels. Results: Both NG-Ox and NG exhibited cytotoxic, genotoxic and apoptotic effects and resulted in increased ROS values in a dose-dependent manner. The effects were more pronounced on cancer cell lines. The cytotoxic, genotoxic and apoptotic effects of NG-Ox were higher than that of NG in all cell lines. Significant correlations were observed between cell viability, DNA damage, apoptosis and ROS, in all cell lines exposed to either NG-Ox or NG. Conclusions: This study showed that both NG-Ox and NG possess cytotoxic, genotoxic and apoptotic activities through the production of ROS on cells, NG-Ox being the more effective one. Therefore, derived compound of NG might be used as antiproliferative agents for the treatment of cancer

Synthesis, characterization and antioxidant capacity of naringenin-oxime

The recognition of the benefits of polyphenolic antioxidants is eliciting increasing interest in the search for new polyphenolic derivatives with improved antioxidant activity. Since naringenin (4'5,7-trihydroxyflavanone) (NG) is one of the most abundant citrus and grapefruit polyphenolics and flavanone oximes were used in the synthesis of anticancer and radioprotector compounds having antiradical activity, the corresponding oxime of NG, naringenin oxime (NG-Ox), was synthesized and investigated. The structure of NG-Ox was characterized by FT-IR, (1)H NMR, elemental analysis, and the synthesized compound was screened for its antioxidant capacity by using the cupric reducing antioxidant capacity (CUPRAC) method. Trolox equivalent antioxidant capacity (TEAC) of NG-Ox was measured to be higher than that of the parent compound, NG. Other parameters of antioxidant activity (scavenging effects on center dot OH, O(2)(center dot-) and H(2)O(2)) of NG-Ox were also determined. (C) 2011 Elsevier B.V. All rights reserved

4-(3-Chloro-2,2-dimethylpropanamido)benzenesulfonamide

In the title compound, C11H15ClN2O3S, the 3-chloro-2,2-dimethylpropanamide and sulfonamide substituents are arranged on opposite sides of the benzene ring plane. In the crystal, molecules are linked by N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds, forming a three-dimensional network

Novel oxime based flavanone, naringin-oxime: Synthesis, characterization and screening for antioxidant activity

Recent interest in polyphenolic antioxidants due to their involvement in health benefits has led to the investigation of new polyphenolic compounds with enhanced antioxidant activity. Naringin (4 ',5,7-tri-hydroxyflavanone-7-beta-L-rhamnoglucoside-(1,2)-alpha-D-glucopyranoside) is one of the major flavanones in citrus and grapefruit. The present study aimed to synthesize naringin oxime from naringin and to evaluate its antioxidant and anticancer potential using in vitro assay system. The structure of the synthesized compound, naringin oxime, was elucidated by FT-IR, H-1 NMR, elemental analysis and UV-vis spectroscopy. Antioxidant capacity of naringin oxime, as measured by the cupric reducing antioxidant capacity (CUPRAC) method, was found to be higher than that of the parent compound naringin. Other parameters of antioxidant activity (scavenging effects on OH center dot, O-2(center dot-), and H2O2) of naringin and naringin oxime were also determined. (C) 2014 Elsevier Ireland Ltd. All rights reserved