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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.
Highlights
Quinones are important compounds widely spread in Nature
We describe the synthesis of new 2- and 2,3-diphenoxy-substituted 1,4-naphthquinone derivatives containing hydrazone, azole, diazole and oxadiazole fragments, and investigation their microbiological activity
Reaction of ester 2 with hydrazine hydrate in 2-propanol under reflux gave 1-(3-hydroxyphenyl)-5-oxo-3-pyrrolidinecarbohydrazide 3, which crystallized from the reaction mixture after cooling
Summary
Quinones are important compounds widely spread in Nature. Compounds containing1,4-naphthoquinone moiety exhibit a broad spectrum of biological activities such as cytotoxic [1,2]antiviral [3,4] anti-inflammatory [5,6] antimalarial [7], antibacterial [8,9], antifungal [10] and antiproliferative properties [11]. Quinones are important compounds widely spread in Nature. 1,4-naphthoquinone moiety exhibit a broad spectrum of biological activities such as cytotoxic [1,2]. Naphthoquinones are important in dye chemistry, and recently they have been used for new infrared dyes in optical recording media [12,13,14]. The aim of this research was to synthesize some new 2,3-disubstituted 1,4-naphthoquinone derivatives and to screen their antibacterial and antifungal activity. The incidence of fungal and bacterial infections has increased dramatically in recent years. The widespread use of antifungal and antibacterial drugs and the development of resistance against them of fungal and bacterial infections has led to serious health hazards. The resistance against wide spectrum antifungal and antibacterial agents has prompted the discovery of new antifungal and antibacterial drugs. The recent pharmacophore modelling approach and three dimensional quantitative structure-activity (3D-QSAR)/comparative molecular similarity indices analysis (CoMSIA) methods applied to 2,3-disubstituted-1,4-naphthoquinones and heterocyclic
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