Synthesis, Antiproliferative Activity and In Silico Studies of Chalcones Derived From 4-(Imidazole-1-yl)Acetophenone

In this study, the synthesis of chalcone compounds (1-11) derived from 4-(imidazol-1-yl)acetophenone and the structure determination of these compounds by various spectroscopic methods were carried out. The anticancer activities of compounds 1-11 were examined against HeLa and PC-3 cancer cells at four different concentrations (100, 50, 25, and 5 µM) using the BrdU ELISA assay. It was determined that all molecules except compounds 1 and 6 in HeLa cancer cells and compounds 2 and 8 against PC-3 cancer cells were more active against HeLa and PC-3 than the standard drug 5-fluorouracil (5-FU). The best activity against PC-3 cancer cells was compound 4 (IC50: 1.39±0.00 µM). In addition, compound 11 (IC50: 1.58±0.01 µM) was found to have the highest activity against HeLa cancer cells. Compound 4 against PC-3 cancer cell and compound 11 against HeLa cancer cell displayed cell selective activity. The ADME properties and drug similarities of the molecules 1-11 using the SwissADME software were investigated. According to these properties, compounds 1-11 were found to obey Lipinski rules

Synthesis of novel chiral sulfonamide-bearing 1,2,4-triazole-3-thione analogs derived from D- and L-phenylalanine esters as potential anti-influenza agents

Novel enantiopure 1,2,4-trizole-3-thiones containing a benzensulfonamide moiety were synthesized via multistep reaction sequence starting with D-phenylalanine methyl ester and L-phenylalanine ethyl ester as a source of chirality. The chemical structures of all compounds were characterized by elemental analysis, UV, IR, (1) H NMR, (13) C NMR, 2D NMR (HETCOR), and mass spectral data. All compounds were tested in vitro antiviral activity against a broad variety of DNA and RNA viruses and in vitro cytostatic activity against murine leukemia (L1210), human T-lymphocyte (CEM) and human cervix carcinoma (HeLa) cell lines. Although enantiopure 1,2,4-triazole-3-thione analogs in (R) configuration emerged as promising anti-influenza A H1N1 subtype in Madin Darby canine kidney cell cultures (MDCK), their enantiomers exhibited no activity. Especially compounds , , , , and (EC50 : 6.5, 6.1, 2.4, 1.6, 1.7 μM, respectively) had excellent activity against influenza A H1N1 subtype compared to the reference drug ribavirin (EC50 : 8.0 μM). Several compounds have been found to inhibit proliferation of L1210, CEM and HeLa cell cultures with IC50 in the 12-53 μM range. Compound and in (R) configuration were the most active compounds (IC50 : 12-22 μM for and IC50 : 19-23 μM for ). Chirality 28:495-513, 2016. © 2016 Wiley Periodicals, Inc.status: publishe

Novel platinum(II) and palladium(II) complexes of thiosemicarbazones derived from 5-substitutedthiophene-2-carboxaldehydes and their antiviral and cytotoxic activities

A series of thiosemicarbazones and their platinum(II) and palladium(II) complexes have been synthesized. The chemical structures of ligands and their complexes were characterized by UV-Vis, IR, (1)H NMR, (13)C NMR, MS spectra, elemental analysis and TGA. The antiviral and cytotoxic activities of all compounds have been tested. Results of broad antiviral evaluation showed that none of the compounds evaluated endowed with anti-DNA or -RNA virus activity at subtoxic concentrations except for the palladium complex 1b. This compound exhibited slightly selective inhibition against cytomegalovirus. The platinum complex 4a exhibited the best cytostatic activities against human cervix carcinoma. Ligands 2, 4 and 5 showed cytostatic potential. The palladium complexes were in general less cytostatic than the corresponding platinum complexes or unliganded congeners.status: publishe

Asetilkolin esteraz inhibitörü olan hidrazid hidrazonlar üzerinde çalışmalar

Amaç: On beş adet hidrazit-hidrazon türevi sentezlenmiş ve asetilkolinesteraz enzimini (AChE) inhibe etme yetenekleri Ellman’ın modifiye spektrofotometrik yöntemi ile değerlendirilmiştir. Yöntem: Anti-asetilkolinesteraz aktivite tayini Ellman’ın modifiye edilmiş spektrofotometrik yöntemi kullanılarak yapılmıştır. Bu spektrofotometrik yöntem bir kromojenik reaktif olan 5,5-ditiyo-bis-(2-nitrobenzoik asit) ile salınan tiyokolinin renkli bir ürün vermesi esasına dayanır. Bulgular: Test edilen bileşikler arasında, 4-fluorobenzoik asit [(4-metoksifenil) metilen] hidrazid(6) ve 2-[(fluorobenzoil) hidrazono]-1,3-dihidroindol-3-on (15), referans ilaç donezepil (IC50=0.054±0.002μM) ile kıyaslandığında kayda değer anti-AChE aktivite göstermiştir. Sonuç: Anti- AChE aktivite sonuçları, p-metoksifenil sübstitüenti taşıyan bileşik 6 ve 1,3-dihidro-indol-3-on sübstitüenti taşıyan bileşik 15’in en aktif bileşikler olduğunu göstermiştir. Aktivite sonuçlarından, hidrazidhidrazon yapısı üzerinde hacimli grupların bulunmasının anti- AChE aktiviteye olumlu yönde katkıda bulunduğu görülmektedir

Synthesis, characterization, spectroscopy, X-ray structure and gaussian hybrid computational investigation of (−)-(S)-1-[2-(benzenesulfonamido)-3-phenylpropanoyl]-4-[(4-methyl)phenyl]thiosemicarbazide

<p>The molecule (−)-(<i>S</i>)-1-[2-(benzenesulfonamido)-3-phenylpropanoyl]-4-[(4-methyl)phenyl] thiosemicarbazide was synthesized and its structure analyzed by X-ray diffraction to understand its geometry, and inter/intra-molecular interactions. Theoretical calculations were carried out using DFT and TD-DFT methods with B3LYP/6-31G(d, p) and B3LYP/6-31G + (d, p) basis sets. Theoretical bond parameters, harmonic vibration frequencies, and chemical shifts are in good agreement with the experimental results. Electronic properties of the molecule derived from frontier orbitals, molecular electrostatic potential, and theoretical UV-Visible spectrum are validated experimentally.</p> <p></p

Synthesis, Characterization, and Biological Evaluation of Some Novel Thiosemicarbazones as Possible Antibacterial and Antioxidant Agents

<div><p> </p><p>The synthesis and characterization of 18 novel thiosemicarbazones have been investigated as part of a research program on development of compounds with antibacterial and antioxidant activities. Among the tested compounds, 2-(4-hydroxybenzylidene)-<i>N</i>-[4-(trifluoromethoxy)phenyl]hydrazine carbothioamide (<b>3g</b>) and 2-(thiophen-2-ylmethylidene)-<i>N</i>-[4-(morpholin-4-yl)phenyl]hydrazine carbothioamide (<b>4b</b>) showed excellent inhibition potency at low concentration (0.5 μg/mL) against Gram-positive pathogens <i>(Enterococcus faecalis</i> and <i>Staphylococcus aureus)</i>. All tested compounds were also found to possess antioxidant activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and 2,2’-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation.</p><p> [Supplementary materials are available for this article. Go to the publisher's online edition of <i>Phosphorus, Sulfur, and Silicon and the Related Elements</i> for the following free supplemental files: Additional text, tables, and figures.]</p></div