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

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\u27-[(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

Nucleophilic substitution reactions of 1,4-naphthoquinone and biologic properties of novel S-, S,S-, N-, and N,S-substituted 1,4-naphthoquinone derivatives

A novel series of S-, S,S-, N- and N,S-substituted 1,4-naphthoquinone derivatives were synthesized and evaluated for their antibacterial and antifungal activity. Among the synthesized compounds especially 10a and 11b have been discovered as an antibacterial or antifungal agents, and 15f is the most effective compound against M. luteum as potent antifungal. The structures of the novel products were characterized by micro analysis, UV/Vis, H-1 NMR, C-13 NMR, and MS. The electrochemical properties of some of the novel 1,4-naphthoquinone derivatives were also investigated by cyclic voltammetry

Synthesis of novel 1,4-naphthoquinone derivatives: antibacterial and antifungal agents

A novel series of substituted 1,4-naphthoquinone derivatives was synthesized and evaluated for antibacterial and antifungal activity. The structures of the novel products were characterized by spectroscopic methods. Among the tested compounds, 3a and 9 are the most effective compounds against M. luteum as potent antibacterial and C. tenuis and A. niger as potent antifungal. These two compounds are promising as biologically active compounds

Synthesis and biological evaluation of novel nitrogen- and sulfur-containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents

1,4-Naphthoquinones are unique reagents in organic synthesis and have been employed in several well known and recently developed areas of application. Furthermore, these 1,4-naphthoquinones have demonstrated high reactivity in nucleophilic vinylic substitutions, in the preparation of sulfurated, (hetero)cyclic and several other transformations. This study describes the synthesis and biological evaluation of derivatives of monosulfurated naphthalene-1,4-dione (3), 3-chloro-2-ethoxy-naphthalene-1,4-dione (4), disulfurated naphthalene-1,4-dione (5), and symmetrical bis-1,4-naphthoquinones (7, 9) were obtained from the reaction of 2,3-dichloro-naphthaquinone (1) with S-, O-substituted mono-, di-, and tetrathiols, respectively. The structures of the novel products were characterized by spectroscopic methods. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved

Synthesis and Antibacterial and Antifungal Properties of Novel S-, N-, N,S-, and S,O-Substituted 1,4-Naphthoquinone Derivatives

A novel series of substituted 1,4-naphthoquinone derivatives were synthesized and evaluated for their antibacterial and antifungal activity. The structures of the novel products were characterized by spectroscopic methods. Among the tested compounds, 2,2,3,3-alkoxy substituted naphthoquinones, S,O-substituted naphthoquinone, and N,S-substituted naphthoquinone derivatives are the most potent antifungals against C. tenuis. 2,3-Thio-2,3-alkoxy substituted naphthoquinones are the most effective antifungal compounds against A. niger. Supplemental materials are available for this article. Go to the publisher's online edition ofPhosphorus, Sulfur, and Silicon and the Related Elementsto view the free supplemental file

Synthesis and antimicrobial properties of 4-acylaminobenzenethiosulfoacid S-esters

AbstractA series of esters of 4-acetyl, 4-trifluoroacetyl- and 4-(3-chloropropionyl)aminobenzenethiosulfoacids (twenty-four compounds) were synthesized and characterized by elemental analysis, 1H NMR and IR spectroscopy. The antibacterial activity of the novel candidates has been screened using the agar diffusion or serial dilution methods against representative Gram-positive (Staphylococcus aureus, Bacillus subtilis, Bacillus mesentericus, Mycobacterium sp., Mycobacterium luteum), Gram-negative (Aeromonas sp., Burkholderia cepacia, Alcaligenes faecalis, Pseudomonas aeruginosa, Escherichia coli, Proteus vulgaris) bacteria and fungi (Candida albicans, Candida tenuis, Candida glabrata, Verticillium dahliae, Trichophyton gypseum, Aspergillus niger, Aspergillus fumigatus, Penicillium chrysogenum). Particular potency has been discovered against all tested pathogenic bacteria and fungi by compounds 1l and 3l at nanomolar concentrations. Some appropriate effect of thiosulfoesters structure upon their antimicrobial activity was determined

Synthesis, antibacterial and antifungal evaluation of thio- or piperazinyl-substituted 1,4-naphthoquinone derivatives

A series of S-, S,S-, S,O-, N- and N,S-derivatives from 2,3-dichloro-1,4-naphthoquinone compound 1 were synthesized in different reaction media and evaluated for their antibacterial and antifungal activities. The structures of the novel products were characterized by spectroscopic methods, such as microanalysis, H-1 NMR, C-13 NMR and MS. Among the tested compounds 9, 12 and 18 are the most effective compounds against Candida tenuis as potent antifungal compounds. Compound 9 is also the most effective compound against Staphylococcus aureus as a potent antifungal compound