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Int. J. Mol. Sci. 2016, 17(5), 766; doi:10.3390/ijms17050766

An Eco-Friendly Ultrasound-Assisted Synthesis of Novel Fluorinated Pyridinium Salts-Based Hydrazones and Antimicrobial and Antitumor Screening

1
Department of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia
2
Department of Chemistry, Faculty of Sciences, University of Sciences and Technology Mohamed Boudiaf, Laboratoire de Chimie and Electrochimie des Complexes Metalliques (LCECM) USTO-MB, P.O. Box 1505, El M`nouar, Oran 31000, Algeria
3
Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Jordan, Amman 11942, Jordan
4
Chemistry Department, Faculty of Science, Alexandria University, Alexandria 21500, Egypt
*
Author to whom correspondence should be addressed.
Academic Editors: Andreas Taubert and Peter Hesemann
Received: 10 April 2016 / Revised: 28 April 2016 / Accepted: 9 May 2016 / Published: 21 May 2016
(This article belongs to the Special Issue Ionic Liquids 2016 and Selected Papers from ILMAT III)
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Abstract

The present work reports an efficient synthesis of fluorinated pyridinium salts-based hydrazones under both conventional and eco-friendly ultrasound procedures. The synthetic approach first involves the preparation of halogenated pyridinium salts through the condensation of isonicotinic acid hydrazide (1) with p-fluorobenzaldehyde (2) followed by the nucleophilic alkylation of the resulting N-(4-fluorobenzylidene)isonicotinohydrazide (3) with a different alkyl iodide. The iodide counteranion of 510 was subjected to an anion exchange metathesis reaction in the presence of an excess of the appropriate metal salts to afford a new series of fluorinated pyridinium salts tethering a hydrazone linkage 1140. Ultrasound irradiation led to higher yields in considerably less time than the conventional methods. The newly synthesized ILs were well-characterized with FT-IR, 1H NMR, 13C NMR, 11B, 19F, 31P and mass spectral analyses. The ILs were also screened for their antimicrobial and antitumor activities. Within the series, the salts tethering fluorinated counter anions 1113, 2123, 3133 and 3638 were found to be more potent against all bacterial and fungal strains at MIC 4–8 µg/mL. The in vitro antiproliferative activity was also investigated against four tumor cell lines (human ductal breast epithelial tumor T47D, human breast adenocarcinoma MCF-7, human epithelial carcinoma HeLa and human epithelial colorectal adenocarcinoma Caco-2) using the MTT assay, which revealed that promising antitumor activity was exhibited by compounds 5, 12 and 14. View Full-Text
Keywords: ultrasound irradiation; hydrazones; metathesis; antimicrobial activity; anticancer activity ultrasound irradiation; hydrazones; metathesis; antimicrobial activity; anticancer activity
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Rezki, N.; Al-Sodies, S.A.; Aouad, M.R.; Bardaweel, S.; Messali, M.; El Ashry, E.S.H. An Eco-Friendly Ultrasound-Assisted Synthesis of Novel Fluorinated Pyridinium Salts-Based Hydrazones and Antimicrobial and Antitumor Screening. Int. J. Mol. Sci. 2016, 17, 766.

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