Mikrobiol. Z. 2017; 79(5):46-56.
Antimicrobial Properties of New Derivatives of Imidazole
Svizhak V.K.1, Dejneka S.E.1, Chornous V.A.1, Azarov O.I.2, Svizhak V.J.2
1Bukovinian State Medical University
2 Teatralna Sq., Chernivtsi, 58002, Ukraine
2Bogomolets National Medical University
13 T. Shevchenko Blvd., Kyiv, 01601, Ukraine
Objective: to study in vitro antimicrobial activity of new derivatives of 2,4-disubstituted 3-(1-aryl-imidazole-5-il) propene-1-one and propane-1-one as the base for further purposeful synthesis of new antimicrobial drugs. Methods. Examination of antimicrobial properties of new chemical synthesis compounds – 8 derivatives of 2,4-disubstituted 3-(1-aryl-imidazole-5-il) propene-1-one and 9 derivatives of 2,4-disubstituted 3-(1-aryl-imidazole-5-il) propane-1-one was carried out by means of generally accepted method of twotime serial dilution in a fluid nutritious medium and detection of minimal bacterio(fungi) static and bactri(fungi)cidal concentrations of compounds concerning reference-strains Staphylococcus aureus АТСС 25923, Escherichia coli АТСС 25922 and Candida albiсans АТСС 885-653. Results. Minimal bacteriostatic concentrations of the majority of the studied derivatives of 2,4-disubstituted 3-(1-aryl-imidazole-5-il) propene-1-one and propane-1-one concerning reference-strains Staphylococcus aureus АТСС 25923 and Escherichia coli АТСС 25922 were found to be within the limits of 31.25 – 125 mkg/ml. Anticandidal activity of the examined compounds was found to prevail over their antibacterial action. Minimal fungistatic concentrations for the majority of the above mentioned compounds concerning Candida albiсans АТСС 885-653 were within the limits from 15.62 to 31.25 mkg/ml, and minimal fungicidal concentrations were from 15.62 to 250 mkg/ml respectively. Introduction of tolyl substitute into the position of 1 imidazole cycle and fluor atoms into the aryl fragment was found to result in increased antimicrobial activity of the examined compounds concerning gram-positive bacteria. Conclusions. The compounds examined manifest moderate anti-microbial activity concerning both gram-positive and gram-negative bacteria, and yeast-like fungi as well. Antimicrobial activity of the examined compounds was found to depend on their chemical structure. The results obtained enable to recommend further purposeful synthesis of new compounds with predicted antimicrobial properties.
Key words: derivatives of 2,4-disubstituted 3-(1-aryl-imidazole-5-yl) propene-1-ones and propane-1-ones, antimicrobial properties, antibacterial activity, antifungal action.
Full text (PDF, in English)
- Laxminarayan R., Duse A., Wattal C. Antibiotic resistance - the need for global solutions. Lancet Infect. Dis. Commission. 2013; 13(2): 1057-98. https://doi.org/10.1016/S1473-3099(13)70318-9
- Leibovici L., Paul M., Garner P., Sinclair D.J. Addressing resistance to antibiotics in systematic reviews of antibiotic interventions. J. Antimicrob. Chemotherapy. 2016; 71(9): 2367-69. https://doi.org/10.1093/jac/dkw135
- Wellington E.M.H., Boxall A.B.A., Cross P., Feil E.J., Gaze W.H. The role of the natural environment in the emergence of antibiotic resistance in Gram-negative bacteria. Lancet Infect. Dis. 2013; 13: 155-65. https://doi.org/10.1016/S1473-3099(12)70317-1
- Amábile-Cuevas C. F. Antibiotics and Antibiotic Resistance in the Environment. Mexico; 2015. https://doi.org/10.1201/b19549-7
- Nathan C., Cars O. Antibiotic Resistance - Problems, Progress, and Prospects. N. Engl. J. Med. 2014; 371: 1761-63. https://doi.org/10.1056/NEJMp1408040
- Sengupta S., Chattopadhyay M.K., Grossart H.-P. The multifaceted roles of antibiotics and antibioticresistance in nature. Frontiers in microbiology. 2013; 4(47): 1-13.
- Spellberg B., Bartlett J.G., Gilbert D.N. The Future of Antibiotics and Resistance. N. Engl. J. Med. 2013; 368: 299-302. https://doi.org/10.1056/NEJMp1215093
- Feschenko Ju.I. Racional’naja antibiotikoterapija bol’nyh s infekcijami niznih dyhatel’nyh putej. Ukrainskij pul’monologi4eskij zurnal. 2009; 4: 117-22. Ukrainian.
- Todosіichuk T.S., Іzdebs’ka T.І., Gromiko O.M., Fedorenko V.O. Suchasnij stan і perspektivi bіotehnologіchnogo virobnictva antibіotikіv. Studia Biologica. 2011; 5(1): 159–72. Ukrainian.
- Zhang L., Peng X.-M., Damu G.L.V., Geng R.-X., Zhou C.-H. Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry. Med. Res. Rev. 2014; 34(2): 340–437. https://doi.org/10.1002/med.21290
- Lamberth C., Dumeunier R., Trah S., Wendeborn S., Godwin J., Schneiter P., Corran A. Synthesis and fungicidal activity of tubulin polymerisation promoters. Part 3: Imidazoles. Bioorg Med Chem. 2013; 21:127–134.
- Metodychni vkazivky 9.9.5-143-2007 «Vyznachennja chutlyvosti mikroorganizmiv do antybakterial’nyh preparativ» [Guidelines 9.9.5-143-2007 “Determination of the sensitivity of microorganisms to antibiotics»]. Kyiv: MOZ Ukrai’ny; 2007. Ukrainian.