Iron(III), nickel(II) and zinc(II) complexes based on acetophenone-S-methyl-thiosemicarbazone: synthesis, characterization, thermogravimetry, and a structural study

New complexes, [Fe(L)Cl], [Ni(L)], and [Zn(L)C2H5OH] (1-3), were synthesized by template reaction of 2-hydroxy-acetophenone-S-methyl-thiosemicarbazone with 2-hydroxy-benzaldehyde. The compounds were characterized by elemental analysis, magnetic measurements, FT-IR, H-1 NMR, UV-visible, and ESI-MS spectra. In these complexes, the ligand is coordinated to the metal ion as dinegatively charged tetradentate chelating agents via the N2O2 donor set. The iron(III) and zinc(II) complexes exhibit square pyramidal geometry whereas the nickel(II) complex has a square planar geometry. The crystal structure of 1, determined by X-ray diffraction method, indicates that 1 crystallizes in the monoclinic space group P21/c with Z=4. Thermal decompositions of the compounds have been investigated using TGA in air

Synthesis of N-, S-, O-substituted quinone dyes and their dyeability on polyester fibers

The aim of this study was synthesis of substituted naphthoquinone derivatives and testing of their dyeability on polyester fibers. There are few studies concerned with dyeing properties of heteroatom-substituted-1,4-naphthoquinone compounds in the literature. A series of N-, S-, O-substituted-1,4-naphthoquinone compounds were synthesized via vinylic substitution. Their structures were determined by infrared spectrometry, H-1 and C-13 nuclear magnetic resonance spectroscopy, mass spectrometry and elemental analysis. The ultraviolet-visible absorption spectra of the dyes were examined in different solvents. The dyes were applied to polyester fibers and dyeing properties were investigated. The rubbing fastness, wash fastness and optical properties of the synthesized compounds also were measured. (C) 2016 Elsevier B.V. All rights reserved

Synthesis, Structural, Spectroscopic and Electrochemical Properties of Novel S- and S,O-Substituted 1,4-Naphthoquinones

New S- and S,O-substituted 1,4-naphthoquinone compounds 3, 4 and 5 were synthesized from the reaction of 2,3-dichloro-1,4-naphthoquinone (1) with 2-mercaptobenzylalcohol (2) in ethanol with sodium carbonate for 2 h at room temperature. The structures of novel compounds were characterized by using micro analysis, FT-IR, UV/Vis, (1)H NMR, (13)C NMR, mass spectra, cyclic voltammetry and fluorescence spectrophotometer. The crystal structure of 3 was determined by X-ray diffraction method. The compound 3 was crystallized in the triclinic crystal system (space group P-1) with the unit cell parameters a = 7.9433(10) angstrom, b = 8.1707(11) angstrom, c = 10.5705(11) angstrom, alpha = 91.173(6)degrees, beta = 93.564(6)degrees, gamma = 106.115(6)degrees

Preparation and Spectral Properties of Novel N,S-Substituted Trichloronitrodienes

The S-substituted nitrodienes were obtained by the reactions of polyhalo-3-nitrobutadiene 1 with some S-nucleophiles [4-(tert-butylbenzyl) thiol, 4-chlorophenylthiol, ethylthiol, and cyclopentylthiol] in directly at room temperature. N, S-Substituted trichloronitrodienes were synthesized from the reactions of the S-substituted nitrodienes with some piperazines in dichloromethane at room temperature. Their structures were characterized by microanalysis, Fourier transform infrared spectroscopy (FT-IR), H-1 nuclear magnetic resonance (H-1 NMR), C-13 nuclear magnetic resonance (C-13-NMR) and mass spectrometry (MS). The high temperature NMR technique was used for determination of methylene protons of piperazine ring in the new compound [4-(1-(2furoyl) piperazin-1-yl]-4-(4-tertbutylbenzyl-sulfanyl)-polyhalo-3-nitro-1,3-butadiene at 45 degrees C and 100 degrees C in DMSO

One-pot synthesis, characterization, and antioxidant capacity of sulfur- and oxygen-substituted 1,4-naphthoquinones and a structural study

In the present study, we reported the one-pot synthesis of S,S- and S,O-substituted 1,4-naphthoquinones, their structural studies, and investigation of their antioxidant activity. The multicomponent reactions of 2,3-dichloro-1,4-naphthoquinone with sulfur- and oxygen-containing nucleophiles were investigated to obtain highly functionalized S,S- and S,O-substituted 1,4-naphthoquinone derivatives. All new compounds were characterized on the basis of H-1, F-19, and C-13 nuclear magnetic resonance spectroscopy, mass spectrometry, and Fourier transform infrared spectroscopy. Crystal structure of 2,3-dihydro-2-(hydroxymethyl)naphtho[2,3-b]-1,4-oxathiin-5,10-dione was determined by X-ray diffraction method. The synthesized compounds were screened for their antioxidant capacity and free radical scavenging activity using the cupric reducing antioxidant capacity method and DPPH method, respectively. 3-Chloro-2-[3-(3-chloro-1,4-dihydro-1,4-dioxonaphthalen-2-yloxy)propylsulfanyl]-1,4-naphthoquinone shows the highest antioxidant capacity with 0.63 cupric reducing antioxidant capacity-trolox equivalent antioxidant capacity coefficient

Synthesis of Tris(Arylthio)-1,3-Butadienes by Nucleophilic Vinylic Substitution of Polyhalogenated Nitrodienes and Structural Elucidation of the Products

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Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells

In the course of biological properties of quinone derivatives, the N(H)-, S- and S,S-substituted-1,4-naphthoquinones were synthesized by reactions of 2,3-dichloro-1,4-naphthoquinone with different amines (2-morpholinoaniline, tert-butyl 4-aminobenzoate, 4-tert- butyl-benzylamine, N-(3-aminopropyl)-2-pipecoline, 2-amino-5,6-dimethylbenzothiazole, N,N'-diphenyl- p-phenylenediamine) and thiolat (sodium 2-methyl-2-propanethiolate). All new products were characterized by MS-ESL UV-Vis, FT-IR, H-1 NMR, C-13 NMR. The antiproliferative activities of these compounds on human cervical cancer (HeLa) cells were evaluated by MTT (3[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide) assay. Although all derivatives inhibited cell growth, the most active compound was 2-(tert-butylthio)-3-chloronaphthalene-1,4-dione 5 (IC50 =10.16 mu M) against the HeLa cells

Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted

A series of new 1,4-naphtho- and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving a Michael addition. In the synthesized compounds, antimicrobial activity at low concentrations against Escherichia coli B-906, Staphylococcus aureus 209-P, and Mycobacterium luteum B-917 bacteria and Candida tenuis VKM Y-70 and Aspergillus niger F-1119 fungi in comparison with controls was identified. 2-Chloro-3-((2-(piperidin-1-yl)ethyl)amino)naphthalene-1,4-dione 3g and 2,5-dichloro-3-ethoxy-6-((2,4,6-trifluorophenyl)amino)cyclohexa-2,5-diene-1,4-dione 17 were the most potent, with a minimum inhibitory concentration value of 15.6 μg/mL against test-culture M. luteum and S. aureus, respectively. Furthermore, in this work, a catalase activity of benzo- and naphthoquinone derivatives was examined for the first time. The catalase activity of benzo- and naphthoquinone derivatives was determined, showing that compound 3g had significant inhibition activity for catalase enzyme

Synthesis, characterization and investigation of antibacterial and antifungal activities of novel 1,3-butadiene compounds

The nitro group-substituted perhalogenobuta-1,3-diene (1) is important synthetic precursor in the synthesis of different heterocycles groups with high biological activity. Firstly, new N,S-substituted-perhalonitro-1,3-butadiene compounds were synthesized by the reactions of various amino or thiol containing nucleophiles with1. The structures of all new compounds have been identified by using spectroscopic techniques (FT-IR,H-1-NMR,C-13-NMR, MS and microanalysis). Secondly, their antimicrobial properties were tested as potential antibacterial and antifungal agents. Antimicrobial activity of synthesized N,S-substituted perhalonitrobutadienes4a-jand5a-dwas evaluated againstEscherichia coliB-906,Staphylococcus aureus209-P, andMycobacterium luteumB-917 bacteria andCandida tenuisVKM Y-70 andAspergillus nigerF-1119 fungi and the compounds4c,4d,5aand5bwith high antifungal action against test-cultureAspergillus nigerat MIC values 0.9-1.9 mu g/cm(3)were identified as the most potent