Synthesis of 9,10-anthracenedione diethyldithiocarbamates

Zvarych, Viktor; Stasevych, Maryna; Лунин, В.В.; Vovk, M. V.; Novikov, Volodymyr

doi:10.1134/s1070363216120227

Cited by 6 publications

(7 citation statements)

References 16 publications

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“…Continuing our research on the search for new substances with practically valuable properties among the functionalized derivatives of 9,10-anthraquinone [19][20][21][22][23], in this work presented herein we report a series of 9,10-anthraquinone derivatives containing dithiocarbamate, thiourea and triazole fragments applied as dyes for the polyester fibers. The sulfur-and nitrogen-containing derivatives 8-18 were prepared via consecutive refunctionalization of aminoanthraquinones 1-7 using methods published in the previous works [15][16][17][18]. The spectral curves of the dyed and the undyed PES fabric samples were shown in Figure 2.…”

Section: Resultsmentioning

confidence: 99%

“…Dye series of 1,8dihydroxy-4,5-dinitroanthracene-9,10-dione and 1,4-dihydroxyanthracene-9,10-dione analogs were synthesized using supercritical carbon dioxide dying conditions [14] In this study, the dyeing properties of a series of derivatives of 9,10-anthraquinone containing dithiocarbamate, thiourea and triazole fragments 8-18, which were prepared via effective consecutive refunctionalization of 1(2)-aminoanthraquinones 1-7, have been investigated for their potential as novel dyes for polyester fiber (Figure 1). The synthesis and the spectral properties of these compounds were reported in our previous studies [15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

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Dyeing of polyester fibers with sulfur- and nitrogen-containing anthraquinone derivatives

Deniz

Sayıl

Öner

et al. 2022

CI&CEQ

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A series of disperse dyes, 9,10-anthraquinone containing dithiocarbamate, thiourea and triazole fragments, were prepared via consecutive refunctionalization of aminoanthraquinones in our previous studies and their structures were confirmed by the 1H, 13C NMR, IR spectra, LC-MS and elemental analysis data. The obtained compounds were applied on polyester fabrics by the exhaustion method at 130?C at pH 4.0-5.0, and their dyeing properties were evaluated by color measurements, the washing fastness test and the light fastness test. Many of these dyes gave solid and level dyeings on polyester fabric with low % concentration of dye. The dyed samples displayed very good color fastnesses. The color change and staining test results were quite good with ratings of ?4-5? or above. The light fastness test results were also satisfactory for the most of the dyed samples.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Dyeing of polyester fibers with sulfur- and nitrogen-containing anthraquinone derivatives

Deniz

Sayıl

Öner

et al. 2022

CI&CEQ

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“…Continuing our research on the directed functionalization of the 9,10-anthraquinone system and the search for new biologically active substances [25][26][27][28][29][30], in the work presented herein we report an effective synthetic approach to a number of new condensed anthraquinone derivatives, namely anthra [1,2-d] [1,2,3]triazine-4,7,12(3H)-triones 22-38 (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones as a New Class of Antistaphylococcal Agents: Synthesis and Biological Evaluation

et al. 2019

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The development and spread of resistance of human pathogenic bacteria to the action of commonly used antibacterial drugs is one of the key problems in modern medicine. One of the especially dangerous and easily developing antibiotic resistant bacterial species is Staphylococcus aureus. Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones 22–38 have been developed as novel effective antistaphylococcal agents. These compounds have been obtained by sequential conversion of 1-amino-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (1) and 1-amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (2) into the corresponding amides 5–21, followed by subsequent endo-cyclization under the influence of sodium nitrite in acetic acid. Evaluation of the antimicrobial activity of the synthesized compounds against selected species of Gram-positive and Gram-negative bacteria as well as pathogenic yeasts of the Candida genus has been carried out by the serial dilution method. It has been established that anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones exhibit selective antibacterial activity against Gram-positive bacteria. Eight, six and seven, out of seventeen compounds tested, effectively inhibited the growth of S. aureus ATCC 25923, S. aureus ATCC 29213 and S. epidermidis ATCC12228, respectively, at a concentration equal to 1 µg/mL or lower. The high antistaphylococcal potential of the most active compounds has been also confirmed against clinical isolates of S. aureus, including the MRSA strains. However, bacteria of the Staphylococcus genus have demonstrated apparent resistance to the novel compounds when grown as a biofilm. None of the four selected compounds 3234 and 36 at a concentration of 64 µg/mL (128 or 256 × MIC—against planktonic cells) has caused any decrease in the metabolic activity of the staphylococcal cells forming the biofilm. The kinetic time–kill assay revealed some important differences in the activity of these substances. Compound 33 is bacteriostatic, while the other three demonstrate bactericidal activity.

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“…Taking into account the practical value of dithiocarbamates both in theoretical and practical significance, in previous works [5,6] we obtained monoand bisdithiocarbamate derivatives of 9,10anthracenediones. Some of the obtained compounds have a powerful biological potential [5,7,8].…”

Section: Introductionmentioning

confidence: 99%

Proton-Initiated Conversion of Dithiocarbamates of 9,10-Anthracenedione

Stasevych¹,

Zvarych²,

Khomyak³

et al. 2018

ChChT

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1 Proton-initiated conversion of dithiocarbamate derivatives of the 9,10-anthracenedione under conditions of acid-catalyzed cyclodehydration using the action of a mixture of H 2 SO 4-AcOH and further treatment with perchloric acid was investigated. Based on the data of the spectral methods (1 H, 13 C NMR, IR, UV spectroscopy), it is established that the reaction stops at the stage of protonation of the sulfur atom of the thiocarbonyl group with the formation of perchlorates. The UV spectra of the obtained perchlorates are characterized by a hypochromic shift with a clearly pronounced absorption maximum.

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Synthesis of 9,10-anthracenedione diethyldithiocarbamates

Cited by 6 publications

References 16 publications

Dyeing of polyester fibers with sulfur- and nitrogen-containing anthraquinone derivatives

Dyeing of polyester fibers with sulfur- and nitrogen-containing anthraquinone derivatives

Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones as a New Class of Antistaphylococcal Agents: Synthesis and Biological Evaluation

Proton-Initiated Conversion of Dithiocarbamates of 9,10-Anthracenedione

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