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• Voskienė, A
• Sapijanskaitė, B
• Mickevičius, V
• Jonuškienė, I
• Stasevych, M
• Komarovska-Porokhnyavets, O
• Musyanovych, R
• Novikov, V
• [+] on Google Scholar
• Voskienė, A
• Sapijanskaitė, B
• Mickevičius, V
• Jonuškienė, I
• Stasevych, M
• Komarovska-Porokhnyavets, O
• Musyanovych, R
• Novikov, V
• [+] on PubMed
• Voskienė, A
• Sapijanskaitė, B
• Mickevičius, V
• Jonuškienė, I
• Stasevych, M
• Komarovska-Porokhnyavets, O
• Musyanovych, R
• Novikov, V

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

Article

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

Aušra Voskienė ¹ , Birutė Sapijanskaitė ¹ , Vytautas Mickevičius ¹ , Ilona Jonuškienė ^1,* , Maryna Stasevych ² , Olena Komarovska-Porokhnyavets ² , Rostyslav Musyanovych ²  and Volodymyr Novikov ²

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; in revised form: 26 November 2012 / Accepted: 3 December 2012 / Published: 5 December 2012

(This article belongs to the Section Organic Synthesis)

Download PDF Full-Text [251 KB, uploaded 5 December 2012 11:18 CET]

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

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