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An improved method for the quaternization of nicotinamide and antifungal activities of its derivatives

Siber, Tamara; Bušić, Valentina; Zobundžija, Dora; Roca, Sunčica; Vikić-Topić, Dražen; Vrandečić, Karolina; Gašo-Sokač, Dajana (2019) An improved method for the quaternization of nicotinamide and antifungal activities of its derivatives. Molecules, 24 (6). ISSN 1420-3049

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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.

Item Type: Article
Uncontrolled Keywords: quaternization ; nicotinamide ; substituted 2-bromoacetophenones ; microwave synthesis ; antifungal activity
Subjects: NATURAL SCIENCES > Chemistry
Divisions: NMR Center
Depositing User: Sunčica Roca
Date Deposited: 10 Mar 2020 16:11
Last Modified: 10 Mar 2020 16:11
URI: http://fulir.irb.hr/id/eprint/5333
DOI: 10.3390/molecules24061001

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