Alkyl sulfonic acide hydrazides: Synthesis, characterization, computational studies and anticancer, antibacterial, anticarbonic anhydrase II (hCA II) activities
| Autor: | Zuhal Karagoz Genc, Suat Tekin, Neslihan Özbek, Ayla Balaban Gündüzalp, Firdevs İlbiz, Fatma Hamurcu, Ümmühan Özmen Özdemir |
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| Přispěvatelé: | Kırşehir Ahi Evran Üniversitesi, Fen-Edebiyat Fakültesi, Kimya Bölümü |
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
Gram-negative bacteria biology Stereochemistry Carbonic anhydrase II Gram-positive bacteria Organic Chemistry Computational studies Bacillus cereus biology.organism_classification Hydrazide Sulfonamide Medicinal chemistry Alkyl sulfonic acide hydrazide Analytical Chemistry Inorganic Chemistry Antibacterial Anti carbonic anhydrase II isoenzyme chemistry.chemical_compound Homologous series Enzyme Anticancer chemistry Spectroscopy |
| Zdroj: | JOURNAL OF MOLECULAR STRUCTURE |
| ISSN: | 0003-6536 |
| Popis: | WOS: 000365361600056 Methane sulfonic acide hydrazide, CH3SO2NHNH2 (1), ethane sulfonic acide hydrazide, CH3CH2SO2NHNH2 (2), propane sulfonic acide hydrazide, CH3CH2CH2SO2NHNH2 (3) and butane sulfonic acide hydrazide, CH3CH2CH2CH2SO2NHNH2 (4) have been synthesized as homologous series and characterized by using elemental analysis, spectrophotometric methods (H-1-C-13 NMR, FT-IR, LC-MS). In order to gain insight into the structure of the compounds, we have performed computational studies by using 6 311G(d, p) functional in which B3LYP functional were implemented. The geometry of the sulfonic acide hydrazides were optimized at the DFT method with Gaussian 09 program package. A conformational analysis of compounds were performed by using NMR theoretical calculations with DFT/B3LYP/6 311++G(2d, 2p) level of theory by applying the (GIAO) approach. The anticancer activities of these compounds on MCF-7 human breast cancer cell line investigated by comparing IC50 values. The antibacterial activities of synthesized compounds were studied against Gram positive bacteria; Staphylococcus aureus ATCC 6538, Bacillus subtilis ATCC 6633, Bacillus cereus NRRL-B-3711, Enterococcus faecalis ATCC 29212 and Gram negative bacteria; Estherichia coli ATCC 11230, Pseudomonas aeruginosa ATCC 15442, Klebsiella pneumonia ATCC 70063 by using the disc diffusion method. The inhibition activities of these compounds on carbonic anhydrase II enzyme (hCA II) have been investigated by comparing IC50 and Ki values. The biological activity screening shows that butane sulfonic acide hydrazide (4) has more activity than the others against tested breast cancer cell lines MCF-7, Gram negative/Gram positive bacteria and carbonic anhydrase II (hCA II) isoenzyme. (C) 2015 Elsevier B.V. All rights reserved. Gazi UniversityGazi University [05/2010-92] This research was supported by Gazi University Research Fund under Project No 05/2010-92. We thank Ankara University, Faculty of Pharmacy. Central Labs, for allocation of time at the Mass Spectra and Elemental Analyses. |
| Databáze: | OpenAIRE |
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