Synthesis and the antimicrobial activity of metalcarbene compounds of the triazole series

N. V. Glinyana, V. Sh. Saberov, A. V. Knishevitsky, N. I. Korotkikh, O. P. Shvaika, O. S. Papayanina, O. Z. Komarovska-Porokhnyavets, V. I. Lubenets, V. P. Novikov

Abstract


Мetalcarbene compounds of a series of [1,2,4] and [1,2,3]triazoles have been synthesized to study their antimicrobial activity. Monocarbene complexes of palladium (9a) and copper(I) (9b,12,15), biscarbene complexes of palladium (4a) and copper(I) (4b,14), a carbenoid complex of cobalt (5) have been synthesized by the direct interaction of stable carbenes with transition metal salts or by analogous in situ reactions. The intermediate sterically hindered carbenes – [1,2,4]triazol-5-ylidenes 3a-c have been isolated in the individual state. Being intermediate in the synthesis of mesoionic complexes 9a,b 1-adamantyl-4-phenyl-[1,2,3]triazole has been synthesized by [3+2]-cycloaddition of 1-adamantylazide to phenylacetylene in the presence of the biscarbene complex of copper(I) iodide 14. Characteristic signals of the carbenoid carbon atoms are detected in the 13С NMR spectra of complexes in the range of 165-203 ppm. A high antimicrobial activity has been found for complexes 5.12; for compound 12 it corresponds to the minimal bacteriostatic concentration (MBsC) 15.6 mkG/mL, the minimal bactericidal concentration (MBcC) 31.2 mkG/mL (М. luteum), and MBsC 31.2 mkG/mL, MBcC 62.5 mkG/mL (S. aureus). The highest activity in the series studied is observed for the carbenoid complex of cobalt (5) on the test-culture of M. luteum (MBsC 15.6 mkG/mL and MBcC 31.2 mkG/mL), and on the test-culture of C. tenuis (the minimal fungistatic concentration is 7.8 mkG/mL and the minimal fungicidal concentration is 31.2 mkG/mL).

Keywords


metalcarbene compounds; antimicrobial activity

References


Marichev К.A., Glinyanaya N.V., Korotkikh N.І., Shvaika О.P., Kiselyov А.V., Knishevitsky А.V., Pekhtereva Т.М., Dudarenko G.V., Komarovska-Porokhnyavets О.P., Novikov V.P., Lubenets V.І. Zhurnal organichnoi ta farmatsevtichnoi khimii – Journal of organic and pharmaceutical chemistry, 2011, Vol. 9, No.3(35), pp.72-79.

Korotkikh N.І., Shvaika О.P., Kiselyov А.V., Knishevitsky А.V., Glinyanaya N.V., Marichev К.A., Novikov V.P., Lubenets V.І., Iskiv О.P., Moskalenko N.I., Komarovska-Porokhnyavets О.P. Visnyk natsionalnogo universitetu „Lvivska polytekhnika” – Herald of National University “Lvivska polytekhnika”, 2008, No.622, pp.3-6.

Liu L., Huang Y., Riduan S.N., Gao S., Yang Y., Fan W., Zhang Y. Main-chain imidazolium oligomer material as a selective biomimetic antimicrobial agent. Biomaterials, 2012, 33, pp.8625-8631. Cited 4 times. DOI: http://dx.doi.org/10.1016/j.biomaterials.2012.08.006

Che C.-M., Sun R.W.-Y. Therapeutic applications of gold complexes: lipophilic gold(III) cations and gold(I) complexes for anti-cancer treatment. Chem. Commun., 2011, 47, pp. 9554-9560. Cited 37 times. DOI: 10.1039/c1cc10860c

Oehninger L., Rubbiani R., Ott I. N-Heterocyclic carbene metal complexes in medicinal chemistry. Dalton Trans., 2013, 42, pp.3269-3284. Cited 29 times. DOI:10.1039/c2dt32617e

Gasser G., Metzler-Nolte N. The potential of organometallic complexes in medicinal chemistry. Cur. Opinion Chem. Biol., 2012, Vol. 16, pp.84-91. Cited 45 times. DOI: 10.1016/j.cbpa.2012.01.013

Liu W., Gust R. Metal N-heterocyclic carbene complexes as potential antitumor metallodrugs. Chem. Soc. Rev., 2013, Vol. 42, 755. Cited 36 times. DOI: 10.1039/c2cs35314h

John A., Ghosh P. Fascinating frontiers of N/O-functionalized N-heterocyclic carbene chemistry: from chemical catalysis to biomedical applications. Dalton Trans., 2010, 39, pp.7183-7206. Cited 61 times. DOI: 10.1039/c002475a

Hemmert C., Fabie A., Fabre A., Benoit-Vical F., Gornitzka H. Synthesis, structures, and antimalarial activities of some silver(I), gold(I) and gold(III) complexes involving N-heterocyclic carbene ligands. Eur. J. Med. Chem., 2013, 60, pp.64-75. Cited 3 times. DOI: http://dx.doi.org/10.1016/j. ejmech.2012.11.038

Weaver J., Gaillard S., Toye C., Macpherson S., Nolan S.P., Riches A. Cytotoxicity of Gold(I) N-Heterocyclic Carbene Complexes Assessed by Using Human Tumor Cell Lines. Chem. Eur. J., 2011, 17, pp.6620-6624. Cited 23 times.

DOI: http://dx.doi.org/10.1016/j.ejmech.2012.11.038

Yan J., Chow A.L.-F., Leung C.-H., Sun R.W.-Y., Ma D.-L., Che C.-M. Cyclometalated gold(III) complexes with N-heterocyclic carbene ligands as topoisomerase I poisons. Chem. Commun., 2010, 46, pp.3893-3895. Cited 36 times. DOI: 10.1039/c001216e

Korotkikh N.I., Saberov V.Sh., Kiselev A.V., Glinyanaya N.V., Marichev K.A., Pekhtereva T.M., Dudarenko G.V., Bumagin N.A., Shvaika O.P. Heterocyclic carbene complexes of nickel, palladium, and copper(I) as effective catalysts for the reduction of ketones. Chemistry of Heterocyclic Compounds, 2012, 47, pp.1551-1560. Cited 0 times. DOI: 10.1007/s10593-012-0947-9

Korotkikh N.I., Kiselev A.V., Knishevitsky A.V., Rayenko G.F., Pekhtereva T.M., Shvaika O.P. Recyclization of 1,3,4-oxadiazoles and bis-1,3,4-oxadiazoles into 1,2,4-triazole derivatives. Synthesis of 5-unsubstituted 1,2,4-triazoles. Chemistry of Heterocyclic compounds, 2005, 7, pp.1026-1032. Cited 2 times. DOI: 10.1007/s10593-005-0240-2

Korotkikh N.І., Cowley А.H., Moore J.А., Glinyanaya N.V., Panov І.S., Rayenko G.F., Pekhtereva T.М., Shvaika О.P. Reaction of 1-tert-butyl-3,4-diphenyl-1,2,4-triazol-5-ylidenes with a malonic ester. Org. Biomol. Chem., 2008, 1, pp.195-199. Cited 5 times. DOI: 10.1039/b712885a.

Chen X., Liu R., Xu Y., Zou G. Tunable protic ionic liquids as solvent-catalysts for improved synthesis of multiply substituted 1,2,4-triazoles from oxadiazoles and organoamines. Tetrahedron, 2012, 68, pp.4813-4819. DOI: 0.1016/j.tet.2012.03.114

Order of the Ukrainian Education and Science Ministry №167 from 05.04.2007 Novosti mediciny i farmacii – News of medicine and pharmacy, 2008, 236, pp.2-4.

Labinskaya А.S. Microbiology with appliances of microbiological studies. – М.: Medicine, 1972, pp.84-93.


GOST Style Citations


—




DOI: https://doi.org/10.24959/ophcj.14.793

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)