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

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

Computer-aided prediction and cytotoxicity evaluation of dithiocarbamates of 9,10-anthracenedione as new anticancer agents

Anticancer activity as an associated action for a series of dithiocarbamates of 9,10-anthracenedione was predicted using the PASS computer program and analysed with PharmaExpert software. The predicted cytotoxic activity of the dithiocarbamate derivatives of 9,10-anthracenedione was evaluated in vitro on cancer cells of the human lung (A549), prostate (PC3), colon (HT29) and human breast (MCF7) using the sulforhodamine B (SRB) cell viability assay. Among these compounds, 9,10-dioxo-9,10-dihydroanthracen-1-yl pyrrolidin-1-carbodithioate and 9,10-dioxo-9,10-dihydroanthracen-2-yl pyrrolidin-1-carbodithioate were identified as the most potent anticancer agents with cytotoxic activity against the MCF-7 human breast cell line with GI(50) values of 1.40 M and 1.52 M, whereas the GI(50) value for the reference anticancer drug mitoxantrone was 3.93 M. Thus, anticancer activity predicted by PASS with a probability Pa > 30% was confirmed by the experiment. Relatively small Pa values estimated by PASS indicated the novelty of the considered derivatives comparing to the compounds from the PASS training set.Ministry of Education and Science of Ukraine, Scientific Research Project - 0116U004138Russian State Academies of Sciences Fundamental Research Programİstanbul Üniversitesi - NP-4562

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, Characterization, and Biological Properties of Novel Piperidinolyl-, Piperidinyl-, and Piperazinyl-Substituted Naphthoquinone Compounds and Their Reactions With Some Thiols

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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