INVESTIGATION OF ANTIBACTERIAL AND ANTIFUNGAL ACTIVITY OF SOME 4-THIOMETHYL FUNCTIONALIZED THIAZOLES
DOI:
https://doi.org/10.32782/pcsd-2023-4-2Keywords:
4-thiomethyl-functionalized 1,3-thiazoles, thioesters, antibacterial activity, antifungal activity, bioscreeningAbstract
The thiazole nucleus is a key element of the structure of such pharmacologically important types compounds as antibiotics (Penicillin, Ceftriaxone, Ampicillin, Cefotaxime, Amoxicillin) and antimicrobial drugs (Myxothiazole, Sulfathiazole, Ethaboxam, Abafungin, Ravuconazole). The prevalence of the thiazole cycle in the above-mentioned drugs is a strong basis for the purposeful search, screening, development and introduction of drugs with antimicrobial action based on it. That is why the present work is dedicated to the study of the antibacterial and antifungal activity of previously synthesized new 1,3-thiazole derivatives exofunctionalized at position 4 with aryl and heteroarylthio substituents. The obtained results of the bioscreening showed that 4-thiomethyl-functionalized 1,3-thiazoles are characterized by moderate bactericidal and fungicidal activities, which were evaluated by the values of the zones of growth inhibition of test cultures, as well as by the values of the minimum bacteriostatic concentration (MBsK) and minimum fungicidal concentration (MfsK) by the method of serial dilutions. It was found that 3-(4-hydroxy-3-methoxyphenyl)-2-(4-((5-nitro-1H-benzo[d] imidazol-2-ylthio)methyl)thiazol-2-yl)acrylonitrile 8 with a MBsK of 31.25 μg/ml against Enterococcus faecalis ATCC 29212 bacteria. When determining the minimum fungistatic concentration by the method of serial dilutions, it was found that compounds 4,7,10,13,14,16,21 were more selective against Candida krusei ATCC 6258 with an MfsK of 15.625-31.25 μg/ml.
References
Lagu, S.B., Yejella, R.P., Bhandare, R.R., Shaik, A.B. Design, synthesis, and antibacterial and antifungal activities of novel trifluoromethyl and trifluoromethoxy substituted chalcone derivatives. Pharmaceuticals. 2020. 13(11). P. 375-391.
Vitaku, E., Smith, D.T., Njardarson, J.T. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J. Med. Chem. 2014. 57. P. 10257-10274.
Mohanty, P., Behera, S., Behura, R., Shubhadarshinee, L., Mohapatra, P., Barick, A.K., Jali, B.R. Antibacterial activity of thiazole and its derivatives: A review. Biointerface Res. Appl. Chem. 2022. 12(2). P. 2171-2195.
Danyliuk, I., Kovalenko, N., Tolmachova, V., Kovtun, O., Saliyeva, L., Slyvka, N., Holota, S., Kutrov, G., Tsapko, M., Vovk, M. Synthesis and antioxidant activity evaluation of some new 4-thiomethyl functionalized 1,3-thiazoles. Curr. Chem. Lett. 2023. 12(4). P. 667-676.
Janowska, S., Andrzejczuk, S., Gawryś, P., Wujec, M. Synthesis and Antimicrobial Activity of New Mannich Bases with Piperazine Moiety. Molecules. 2023. 28(14). P. 5562–14776.
Nazarchuk, O. A. Antiseptics: modern strategy of struggle with causing agents of the іnfection complications. Klin Khir. 2016. 9. P. 59-61.
Crowley, P.D., Gallagher, H.C. Clotrimazole as a pharmaceutical: past, present and future. J. Appl. Microbiol. 2014. 117(3). P. 611–617.
