Antileishmanial activity study and theoretical calculations for 4-amino-1,2,4-triazole derivatives

WOS: 0004038557000114-amino-1,2,4-triazole derivatives; 4-amino-1-((5-mercapto-1,3,4-oxadiazole-2-yl)methyl)-3-(thiophene-2-ylmethyl)-1H-1,2,4-triazole-5(4H)-one (1) and 4 -amino-1-((4-amino-5 mercapto-4H-1,2,4triazole-3-yl)rnethyl)-3-(thiophene-2-ylmethyl)-1H-1,2,4-triazole-5(4H)-one (2) were studied theoretically by Density Functional Theory (DFT) method with 6-311++G(d,p) basis set, structural and some spectroscopic parameters were determined. Significant differences between the experimental and calculated values of vibrational frequencies and chemical shifts were explained by the presence of intermolecular (S-H center dot O and S-H center dot center dot N type) hydrogen bonds in structures. The Molecular Electrostatic Potential (MEP) maps obtained at B3LYP/6-311G++(d,p) support the existence of hydrogen bonds. Compounds were tested against to Leishmania infantum promastigots by microdilution broth assay with Alamar Blue Dye. Antileishmanial activity of 4-amino-1,2,4-triazole derivative (2) is remarkable. (C) 2017 Elsevier B.V. All rights reserved

Spectroscopic characterization and density functional studies of new thiadiazole 1,1-dioxide compounds

3rd International Turkish Congress on Molecular Spectroscopy (TURCMOS) -- AUG 26-29, 2017 -- Bodrum, TURKEYWOS: 000449132500007New thiadiazole compounds, 3-imino-4-(anthracene-9-yl)-1,2,5-thiadiazolidine 1,1-dioxide (I) and 3-imino-4-(10-chloroanthracene-9-yl)-1,2,5-thiadiazolidine 1,1-dioxide (II) were synthesized and characterized by Fourier Transform Infrared Spectroscopy (FTIR), C-13 and H-1 NMR and UV-vis spectroscopic methods. Calculations of molecular geometries and spectroscopic parameters were performed using DFT/6-311++G(d,p) method. Frontier Molecular Orbitals (FMOs), Non-Linear Optical (NLO) properties and Molecular Electrostatic Potential (MEP) maps of newly synthesised compounds were obtained. The some considerable differences between experimental and calculated vibrational frequencies and NMR chemical shift values can be attributed to the presence of N-H center dot center dot center dot O type intermolecular hydrogen bonds in the molecular structures of both compounds. NLO properties of compounds were determined by using the mean polarizability (alpha) and the first-order hyperpolarizability (beta) values calculated as 36.8326 x 10(-24)/18.7571 x 10(-31) esu for I, 36.9489 x 10(-24)/31.6544 x 10(-31) esu for II, respectively at the mentioned computational level. These values are greater than the ones of urea (alpha = 4.9067 x 10(-24) and beta = 7.8782 x 10(-31) esu) and therefore, NLO properties study demonstrates that the both compounds, especially compound II, can be suggested as a good nonlinear optical material. (C) 2018 Elsevier B.V. All rights reserved.Ordu University, Scientific Research Projects Co-ordination Department (ODU/BAP) [HD-1611]We thank the Ordu University, Scientific Research Projects Co-ordination Department (ODU/BAP) for their financial support (No. HD-1611)

5-Phenyl thiophene amino phenol derivatives: Synthesis, spectroscopic characterization, computational study and antimicrobial activity

WOS: 000458618500005(((5-phenylthiophen-2-yl) methylene) amino) phenol derivatives were synthezised and characterized by IR and NMR. The density functional theory (DFT) method with 6-311++G (d,p) basis set was used for both calculations of molecular geometries and spectroscopic parameters. Frontier molecular orbitals and molecular electrostatic potential maps for compounds la, lb and lc were obtained. Due to the differences observed in the theoretical spectral parameters, N-H center dot center dot center dot O type intermolecular/intramolecular hydrogen bonds in the molecular structures of compounds were proposed. To determine the nonlinear optical properties of compounds, the mean polarizability (a) and the first hyperpolarizability ((3) obtained as 44.2388 x 10(-24) esu and 373.1267 x 10(-31) esu for compound 1a, 43.8141 x 10(-24) esu and 195.2893 x 10(-31) esu for compound 1b, 36.9489 x 10(-24) esu and 120.73825 x 10(-31) esu for compound 1c, respectively were used. These values indicate that compounds can be suggested as a good nonlinear optical material. In addition, the antimicrobial properties of compounds were investigated by considering antileishmanial and antibacterial activities. The compounds were evaluated against Leishmania infantum promastigots for antileishmanial activity and against five standard bacteria (Escherichia coli, Shigella flexneri, Yersinia enterocolitica, Salmonella typhimurium and Salmonella enterica) for antibacterial activity, by microdilution broth assay with Alamar Blue Dye. Results show that only compound la has high antileishmanial activity and can be evaluated in leishmaniasis treatment after in vivo studies and also considered in pharmacological studies for antibacterial activity. (C) 2019 Published by Elsevier B.V

New Chalcone Derivative: Synthesis, Characterization, Computational Studies and Antioxidant Activity

Ozdemir, Namik/0000-0003-3371-9874WOS: 000505999500006A new chalcone derivative, called as 1-(4-(benzylideneamino)phenyl)-3-(furan-2-yl)prop-2-en-1-one (I), was synthezised and characterized by spectral methods (infrared (IR) and proton and carbon-13 nuclear magnetic resonance (H-1- and C-13-NMR) spectroscopy). A computational study was performed by the density functional theory (DFT) method. Spectral data of compound I optimized by using 6-311G(d,p) and 6-311++G(d,p) basis sets were obtained by 6-311++G(d,p) basis set. The E-Z isomerism for newly synthesized chalcone derivative was investigated by considering four isomeric form, E/E, E/Z, Z/E and Z/Z. The results show that, as assumed and thus named, the chalcone DOI: derivative is in the E/E form. In addition, quantum chemical parameters were calculated by using DFT method with 6-311++(d,p) basis set. Antioxidant activity of compound I was determined by the feiric reducing ability of plasma (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay methods. Compound I has low antioxidant activity.Karadeniz Technical UniversityKaradeniz Teknik UniversityThis study was supported by grants from Karadeniz Technical University

EXPERIMENTAL AND THEORETICAL STUDIES OF 4-[(4-METHYL-5-PHENYL-4H1,2,4-TRIAZOL-3-YL)SULFANYL]BENZENE-1,2-DICARBONITRILE

AKCAY, Hakki Turker/0000-0002-8502-9608; Vazquez-Lopez, Ezequiel M./0000-0002-6012-0931; Hokelek, Tuncer/0000-0002-8602-4382WOS: 000392794300003In this study, 4-[(4-methy1-5-pheny1-4H-1,2,4-triazol-3-yl)sulfanyl]benzene-1,2-dicarbonitrile was synthesized and its molecular structure was characterized by means of FT-IR. and X-ray diffraction methods. the crystal is monoclinic and belongs to the P21/n space group. There are three weak intermolecular C-H...N type hydrogen bonds in the molecular structure. the geometrical parameters, vibration frequencies, HOMO LUMO energies, and molecular electrostatic potential (MEP) map of the compound (3) in ground state were calculated by using density functional theory (DFT/B3LYP) with the 6-311G(d) basis set. Calculated geometrical parameters were compared with X-ray diffraction geometric parameters. on the other hand, theoretical and experimental FT-IR results were also compared.Higher Education CouncilThe author would like to thank the Higher Education Council for supporting this study within international research

1,2,4-triazole derivatives with morpholine; DFT study and antileishmanial activity

1,2,4-triazole derivatives with morpholine; 4-((3-methylthiophene-2-yl) methylenamino)-1-((4-(3-methylthiophene-2-yl) methylene amino)-1-(morpholinomethyl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-3-yl) methyl)-3-(thiophene-2-ylmethyl)-1H-1,2,4-triazole-5(4H)-one (compound I) and 1-((1-(morpholinomethyl)-4-(5-nitrothiophene-2-yl) methyleneamino)-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-3-yl) methyl)4-(( 5-nitrothiophene-2-yl) methyleneamino)-3-(thiophene-2-ylmethyl)-1H-1,2,4-triazole-5(4H)-one (compound II), were optimized using a density functional theory (DFT) method with 6-311G(d,p) basis set and structural and spectral parameters were determined. In vitro antileishmanial activities of compounds were performed against Leishmania infantum promastigots by microdilution broth assay with Alamar Blue dye. Amphotericin B was used as standard drug. The results show that both compounds are antiparasitic and especially compound II has considerable antileishmanial activity due to the minimal inhibitory concentration value of 312 mu g/mL