Synthesis and Antimicrobial Activity of Nitrogen-Containing Anthraquinone Derivatives
DOI:
https://doi.org/10.31351/vol31iss2pp193-201Keywords:
antimicrobial activity, nucleophilic substitution, anthraquinone derivatives, triazenes, fungicidal activityAbstract
New substituted anthraquinones with amino derivations fragments were synthesized through the substitution of bromine atom by different amines using the Ullmann coupling reaction. Obtained compounds based on anthraquinone used for experimental antimicrobial studies. The structure of the synthesized compounds was confirmed by LC-MS and 1H, 13C NMR spectroscopy. Studies on planktonic microorganisms have shown that the first synthesized anthraquinone derivatives have an inhibitory effect against bacteria and fungi. The triazene 1-(3-(benzoic acid(triaz-1-en-1-ol(-4-(1H-imidazol-1-yl(-9,10-dioxo-9,10-dihydroanthracene -2-sulfonic acid, have wide spectrum of activity, growth retardation zones against gram-positive microorganisms in the range of 8.41-11.5 mm, gram-negative bacteria 5.87-8.18 mm, fungi of the genus Candida 5.81-7.48 mm. The high antimicrobial activity of this compound is probably due to the presence of benzoic acid in its molecule.
How to Cite
Publication Dates
References
Malik E, Muller C. Anthraquinones as pharmacological tools and drugs. Medicinal Research Reviews. 2016; 36(4):705–748.
Marzouk B, Marzouk Z, Decor R et al. Antibacterial and anticandidal screening of Tunisian Citrullus colocynthis Schrad. from Medenine. J. Ethnopharmacol. 2009; 125(2):344–349.
Subedi YP, Alfindee MN, Shrestha JP, Chang T. Tuning the biological activity of cationic anthraquinone analogues specifically toward Staphylococcus aureus. Eur. J. Med. Chem. 2018; 157:683–690.
Wuthi-udomlert M, Kupittayanant P, Gritsanapan W. In vitro evaluation of antifungal activity of anthraquinone derivatives of Senna alata. J Health Res. 2010; 24(3):117–122.
Stasevych M, Zvarych V, Lunin V, Halenova T, Savchuk O, Dudchak O, Vovk M, Novikov V. Novel anthraquinone-based derivatives as potent inhibitors for receptor tyrosine kinases. Indian J. Pharm. Sci. 2015; 77:634–637.
Rubin JE, Ball KR, Chirino-Trejo M. Antimicrobial susceptibility of Staphylococcus aureus and Staphylococcus pseudintermedius isolated from various animals. Can. Vet. J. 2011; 52:153–157.
Gouda MA, Berghot MA, Shoeib AI, Khalil AM. Synthesis and antimicrobial of new anthraquinone derivatives incorporating pyrazole moiety. European Journal of Medicinal Chemistry. 2010; 45:1843–1848.
Stasevych M, Zvarych V, Lunin V, et. all. Synthesis and investigation of antimicrobial and antioxidant activity of anthraquinonylhydrazones. Monatshefte für Chemie - Chemical Monthly. 2018; 149:1111–1119.
Stasevych MV, Zvarych VI, Lunin VV, Khomyak SV, Vovk MV, Novikov VP. Synthesis of pyrazole and tetrazole derivatives of 9,10-anthraquinonylhydrazones. Chem. Heterocycl. Compd. 2017; 53:942–944.
Zvarych VI, Stasevych MV, Stanko OV, Komarovskaya-Porokhnyavets EZ, Poroikov VV, Rudik AV, Lagunin AA, Vovk MV, Novikov VP. Computerized prediction, synthesis, and antimicrobial activity of new amino-acid derivatives of 2-Chloro-N-(9,10-Dioxo-9,10-Dihydroanthracen-1-yl)acetamide. Pharm. Chem. J. 2014; 48:584–588.
Shupenyuk V, Taras T, Sabadakh O, Luchkevich E, Kornii Y. Synthesis some 4-substituted 9,10-anthraquinones. French-Ukrainian Journal of Chemistry. 2020; 8(1):58-65.
Shupeniuk V, Amaladoss N, Sabadakh O, Taras T, Matkivsky M. Synthesis of 4-substituted primary aliphatic aminoanthraquinones and in silico studies. Russ. J. Org. Chem. 2021; 57 (4):582-588.
Sabadakh O, Taras T, Luchkevich E, Novikov V. Synthesis of triazene derivatives of 9,10-anthraquinone. Russ. J. Org. Chem. 2015; 51(2):277–278.
Downloads
Published
Issue
Section
License
Copyright (c) 2022 Iraqi Journal of Pharmaceutical Sciences ( P-ISSN 1683 - 3597 E-ISSN 2521 - 3512)
This work is licensed under a Creative Commons Attribution 4.0 International License.
