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Molecules 2012, 17(12), 14434-14448; doi:10.3390/molecules171214434

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

1
Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, Lithuania
2
Department of Technology of Biologically Active Substances, Pharmacy Biotechnology, National University “Lviv Politechnic” Bandera str. 12, 79013, Lviv-13, Ukraine
*
Author to whom correspondence should be addressed.
Received: 9 October 2012 / Revised: 26 November 2012 / Accepted: 3 December 2012 / Published: 5 December 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

New 3-substituted 1-(3-hydroxyphenyl)-5-oxopyrrolidine derivatives containing hydrazone, azole, diazole, oxadiazole fragments, as well as 2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinone derivatives were synthesized. The structure of all compounds has been confirmed by NMR, IR, mass spectra, and elemental analysis data. Methyl 1-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)oxy]phenyl}-5-oxo-3-pyrrolidinecarboxylate demonstrated potential antibacterial and antifungal activities as determined by diffusion and serial dilution methods, while N'-[(4-bromophenyl)methylidene]-1-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)oxy]phenyl}-5-oxo-3-pyrrolidinecarbohydrazide and 2-{3-[4-(1,2,3-oxadiazol-5-yl)-2-oxo-1-pyrrolidinyl]phenoxy}-3-{3-[4-(1,3,4-oxadiazol-2-yl)-2-oxo- 1-pyrrolidinyl]phenoxy}naphthoquinone showed antifungal activity against Candida tenuis and Aspergillus niger at low concentrations, as determined by the serial dilution method. The substitution of the methoxy fragment by N-containing substituents in monophenoxy substituted naphthoquinones was found to decrease their activity against Mycobacterium luteum. Besides, introduction of the second phenoxy substituted fragment increased the antifungal activity against Candida tenuis and Aspergillus niger at lower concentrations.
Keywords: 3-substituted 1-(3-hydroxyphenyl)-5-oxopyrrolidine derivatives; 1,4-naphtho-quinone; antibacterial activity; antifungal activity 3-substituted 1-(3-hydroxyphenyl)-5-oxopyrrolidine derivatives; 1,4-naphtho-quinone; antibacterial activity; antifungal activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Voskienė, A.; Sapijanskaitė, B.; Mickevičius, V.; Jonuškienė, I.; Stasevych, M.; Komarovska-Porokhnyavets, O.; Musyanovych, R.; Novikov, V. Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties. Molecules 2012, 17, 14434-14448.

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