Synthesis and antimicrobial activity of 4-chloro-5-(2-nitrovinyl)-1H-imidazoles and products of their interaction with 3-methyl-2-pyrazolin-5-one

V. O. Chornous, O. Ya. Mel’nyk, A. M. Grozav, N. D. Yakovychuk, M. V. Vovk

Abstract


The work is devoted to the synthesis of new derivatives of 5-(2-nitrovinyl)imidazole, investigation of their chemical behaviour in the Michael reaction with heterocyclic CH-acids and study of their antifungal and antibacterial action. It has been found that 1-substituted 4-chloro-5-(2-nitrovinyl)imidazoles can be prepared with 71-83% yields by heating 4-chloro-5-formylimidazoles with the excess of nitromethane or nitroethane in the presence of anhydrous ammonium acetate. The compounds synthesized are typical representatives of activated alkenes and react with 3-methyl-2-pyrazolin-5-one in the Michael reaction. It has been shown that when refluxing in water for 3 h the interaction proceeds regioselectively with the most nucleophilic C4 atom of pyrazolinone giving 4-[1-(4-chloro-1H-imidazole-5-yl)-2-nitroalkyl]-5-methyl-1H-pyrazol-3-oles. In the case of the spatially hindered exocyclic part of the molecule 1H NMR spectra have characteristic features. The biological screening results of the compounds obtained have confirmed a high bactericidal and fungicidal effect. It has been found that antimicrobial properties are dependent on the nature of the substituent in the position 1 of the imidazole cycle and the structure of the exocyclic fragment. In particular, the condensation products of 4-chloroimidazol-5-carbaldehyde with nitroethane showed 4-6 times higher bactericidal activity compared to the analogous compounds obtained from nitromethane.


Keywords


4-chloro-5-formylimidazoles; nitroalkanes; 3-methyl-2-pyrazolin-5-one; 4-chloro-5-(2-nitrovinyl)imidazoles; 4-[1-(4-chloroimidazol-5-yl)-2-nitroalkyl]-5-methyl-1H-pyrazol-3-oles; antifungal and bactericidal activity

References


Mashkovskiy M. D. Lekarstvennyie sredstva. 16-e izd., pererab., ispr. i dop. – M.: Novaya volna, 2012, pp.917-924.

Рostanova Kabinetu ministriv Ukrayiny, №333 vid 25.03.2009.

Verma A., Joshi S., Singh D. Journal of Chemistry, 2013, Vol. 2013, pp.1-12. doi:10.1155/2013/329412

Aleksandrova E. V., Kravchenko A. N., Kochergin P. M. Khimiya heterotsyklicheskikh soedinenii – Chemistry of heterocyclic compounds, 2011, Vol. 46, No.11, pp.1295-1317. doi:10.1007/s10593-011-0666-7

Pat. WO 2012141338 A1. Chen X., Haraguchi Y., Hashizume H; Publication Date: 18.10.2012.

Cavalleri B., Volpe G., Arioli V. Journal of Medical Chemistry, 1977, Vol. 20, No.5, pp.656-660. doi:10.1021/jm00215a007

Hrozav A. M., Chornous V. O., Palamar A. O., Demydovska S. A., Vovk M. V. Farmatsevtychnyy zhurnal, 2012, No.6, pp.61-67.

Chornous V. O., Palamar A. O., Yaremiy I. M., Burdenyk I. P., Vovk M. V. Visnyk farmatsiyi, 2013, Vol, No.74, pp.30-33.

Chornous V. A., Grozav A. N., Todoriko L. D., Vovk M. V. Khimiko-farmatsevticheskiy zhurnal – Pharmaceutical Chemistry Journal, 2013, Vol. 47, No.10, pp.71-73. doi:10.1007/s11094-014-0996-8

Yet L. In Comprehensive Heterocyclic Chemistry III. Katritzky A. R., Ramsden C. A., Scriven E. F. V., Taylor R. J. K.: Elsevier Ltd: USA, 2008, Vol. 4.2, pp.145-388. doi:10.1016/B978-008044992-0.00402-8

Meshram H. M., Kumar N. S., Nanubolu J. B., Rao L. Ch., Rao N. N. Tetrahedron Letters, 2013, Vol. 54, No.45, pp.5941-5949. doi:10.1016/j.tetlet.2013.08.042

Li J.-H, Du D-M. Organic Biomolecular Chemistry, 2013, Vol. 11, No.38, pp. 6215-6223. doi:10.1039/C3OB41045E

Pershin G. N. Metody eksperimentalnoy khimioterapii. – M., 1959, pp.109-111.


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DOI: https://doi.org/10.24959/ophcj.14.808

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