New 1-(2-aryloxyethyl- and 2-halobenzyl)-3-(2-hydroxyethyl)-2-imino-1,3-dihydrobenzimidazoline hydrochlorides were synthesized via reactions of 1-(2-aryloxyethyl- and 2-halobenzyl)-2-aminobenzimidazoles with ethylenechlorohydrin. These compounds were shown to possess both bactericidal activity against some pathogenic Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Escherichia coli) and pronounced protistocidal activity against the species Colpoda steinii.
Similar content being viewed by others
Notes
Here and further primed numbers denote positions on the N1-aryl substituent.
References
R. Walia, M. Hedaitullah, S. F. Naaz, et al., Int. J. Res. Pharm. Chem., 1(3), 565 – 574 (2011).
A. Khalafi-Nezhad, M. N. Soltani Rad, H. Mohabatkar, et al., Bioorg. Med. Chem., 5(13), 1931 – 1938 (2005).
Y. Ozkay, Y. Tunall, H. Karaca, et al., Arch. Pharm. Res., 34(9), 1427 – 1435 (2011).
O. O. Ajani, E. K. Ezeoke, A. Edobor-Osoh, et al., Int. Res. J. Pure Appl. Chem., 3(1), 10 – 21 (2013).
P. S. Charifson, D. D. Deiniger, et al., US Pat. Appl. No. 20050256136 A1, Nov. 17, 2005; https: // docs.google.com / a / google.com / viewer’url=www.google.com / patents / US20050256136.pdf.
P. S. Charifson, A.-L. Grillot, T. H. Grossman, et al., J. Med. Chem., 51, 5243 – 5263 (2008).
A. S. Morkovnik, L. N. Divaeva, et al., RU Pat. No. 2,423,355 (A), Mar. 27, 2011; - (C2), Oct. 7, 2011; Byull. Izobret., No. 19 (2011).
A. S. Morkovnik, L. N. Divaeva, T. A. Kuz’menko, et al., in: Abstracts of Papers of the VIIth All-Russian Conference “Chemistry and Medicine” [in Russian], ORKhI-MED-2009, Ufa, 2009, pp. 57 – 58.
L. A. Karpinskaya, O. I. Kiselev, A. S. Morkovnik, et al., in: Abstracts of the 3 rd International Meeting Influenza, Muenster, 2012, Abstrs. 67.
L. A. Karpinskaya, V. V. Zarubaev, O. I. Kiselev, et al., in: Abstracts of the 26 th International Conference on Antiviral Research, San Francisco, 2013, Abstrs. 54.
L. N. Divaeva, A. S. Morkovnik, A. A. Zubenko, et al., Khim-farm. Zh., 48(10), 29 – 32 (2014); Pharm. Chem. J., 48(10), 661 – 664 (2015).
A. I. Klimenko, A. A. Zubenko, et al., RU Pat. No. 2,477,129, Jan. 27, 2013; Byull. Izobret., No. 7, (2013).
A. S. Morkovnik, L. N. Divaeva, I. S. Vasilchenko, et al., Mendeleev Commun., 17, 224 – 226 (2007).
R. U. Khabriev (ed.), Handbook of Experimental (Preclinical) Study of New Drugs [in Russian], Meditsina, Moscow, 2005.
A. N. Mironov (ed.), Handbook of Preclinical Studies of Drugs [in Russian], Part 1, Grif i K, Moscow, 2012.
Determination of microorganism sensitivity to antibacterial drugs. Methodical instructions [in Russian], MUK 4.2.1890 – 04 (2004).
G. N. Pershin, Methods of Experimental Chemotherapy [in Russian], Meditsina, Moscow, 1971, pp. 100 – 106.
L. N. Fetisov, A. A. Zubenko, A. N. Bodryakov, et al., in: Abstracts of Papers of the International Parasitological Symposium “Current Problems of General and Special Parasitology” [in Russian], Novocherkassk, 2012; publ. in the information-analytical journal Voprosy Normativno-pravovogo Regulirovaniya v Veterinarii, No. 4, 1 – 2012 (ISSN 2072-6023), pp. 70 – 73.
I. V. Berezovskaya, Khim.-farm. Zh., 37(3), 32 – 34 (2003); Pharm. Chem. J., 37(3), 139 – 141 (2003).
Acknowledgments
The work was performed under a project of a state contract for scientific activity of IPOC, SFU, Project No. 4.196.2014/K. Equipment of the CCU Molecular Spectroscopy, IPOC, SFU, was used in the work.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 49, No. 2, pp. 21 – 25, February, 2015.
Rights and permissions
About this article
Cite this article
Divaeva, L.N., Klimenko, A.I., Morkovnik, A.S. et al. Synthesis and Antimicrobial and Protistocidal Activity of 1-(2-Aryloxyethyl- and 2-Halobenzyl)-3-(2-Hydroxyethyl)-2-Imino-1,3-Dihydrobenzimidazolines. Pharm Chem J 49, 91–95 (2015). https://doi.org/10.1007/s11094-015-1228-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-015-1228-6