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Open AccessArticle

An Improved Method for the Quaternization of Nicotinamide and Antifungal Activities of Its Derivatives

1
Faculty of Agrobiotechnical Sciences, Josip Juraj Strossmayer University of Osijek, Vladimira Preloga 1, HR–31000 Osijek, Croatia
2
Faculty of Food Technology, Josip Juraj Strossmayer University of Osijek, Kuhačeva 20, HR–31000 Osijek, Croatia
3
NMR Centre, Ruđer Bošković Institute, Bijenička cesta 54, HR–10000 Zagreb, Croatia
4
Department of Natural and Health Sciences, Juraj Dobrila University of Pula, Zagrebačka 30, HR–52100 Pula, Croatia
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(6), 1001; https://doi.org/10.3390/molecules24061001
Received: 27 February 2019 / Revised: 7 March 2019 / Accepted: 9 March 2019 / Published: 13 March 2019
(This article belongs to the Special Issue New Studies on the Synthesis of Biologically Active Products)
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Abstract

The quaternization reactions of nicotinamide, with different electrophiles: methyl iodide and substituted 2-bromoacetophenones (4-Cl, 4-Br, 4-H, 4-CH3, 4-F, 4-OCH3, 4-Ph, 2-OCH3, 4-NO2) are reported. The preparations were carried out by conventional synthesis and under microwave irradiation in absolute ethanol and acetone. The synthesis performed by microwave dielectric heating significantly improved yield, up to 8 times, and shortened down the reaction time from ca. one day in conventional, to 10–20 min. The structures of the synthesized compounds were confirmed by IR, 1H- and 13C-NMR spectroscopy, mass spectrometry and elemental analysis. The compounds have been screened for antifungal activities against Fusarium oxysporum, Fusarium culmorum, Macrophomina phaseolina and Sclerotinia sclerotiorum at concentrations of 10 µg/mL and 100 µg/mL. Six compounds showed the strong inhibition of mycelium growth at a concentration of 10 µg/mL. All tested compounds revealed the great inhibitory activities against S. sclerotiorum at a concentration of 100 µg/mL. View Full-Text
Keywords: quaternization; nicotinamide; substituted 2-bromoacetophenones; microwave synthesis; antifungal activity quaternization; nicotinamide; substituted 2-bromoacetophenones; microwave synthesis; antifungal activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Siber, T.; Bušić, V.; Zobundžija, D.; Roca, S.; Vikić-Topić, D.; Vrandečić, K.; Gašo-Sokač, D. An Improved Method for the Quaternization of Nicotinamide and Antifungal Activities of Its Derivatives. Molecules 2019, 24, 1001.

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