SEARCH WITHIN CONTENT
Citation Information : Polish Journal of Microbiology. Volume 65, Issue 3, Pages 359-364, DOI: https://doi.org/10.5604/17331331.1215615
License : (CC BY-NC-ND 4.0)
Received Date : 16-December-2014 / Accepted: 11-February-2016 / Published Online: 26-August-2016
A broad series of 4,5,6,7-tetrahalogenated benzimidazoles and 4-(1H-benzimidazol-2-yl)-benzene-1,3-diol derivatives was tested against selected bacteria and fungi. For this study three plant pathogens Colletotrichum sp., Fusarium sp., and Sclerotinia sp., as well as Staphylococcus sp., Enterococcus sp., Escherichia sp., Enterobacter sp., Klebsiella spp. , and Candida spp. as human pathogens were used. MIC values and/or area of growth reduction method were applied in order to compare the activity of the synthesized compounds. From the presented set of 22 compounds, only 8, 16, 18 and 19 showed moderate to good inhibition against bacterial strains. Against Candida strains only compound 19 with three hydroxyl substituted benzene moiety presented high inhibition at nystatin level or lower.
Andrzejewska M., L. Yepez-Mulia, A. Tapia, R. Cedillo-Rivera, A.E. Laudy, B.J. Starościak and Z. Kazimierczuk. 2004. Synthesis, and antiprotozoal and antibacterial activities of S-substituted 4,6-dibromo- and 4,6-dichloro-2-mercaptobenzimidazoles. Eur. J. Pharm. Sci. 21: 323–329.
Bansal Y. and O. Silakari. 2012. The therapeutic journey of benzimidazoles: a review. Bioorg. Med. Chem. 20: 6208–6236.
Gaba M., S. Singh and C. Mohan. 2014. Benzimidazole: an emerging scaffold for analgesic and anti-inflammatory agents. Eur. J. Med. Chem. 76: 494–505.
Gianoncelli A., G. Cozza, A. Orzeszko, F. Meggio, Z. Kazimierczuk and L. A. Pinna. 2009. Tetraiodobenzimidazoles are potent inhibitors of protein kinase CK2. Bioorg. Med. Chem. 17: 7281–7289.
Horton D.A., G.T. Bourne and M. L. Smythe. 2003. The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem. Rev. 103: 893–930.
Janeczko M., A. Orzeszko, Z. Kazimierczuk, R. Szyszka and A. Baier. 2012. CK2α and CK2α’ subunits differ in their sensitivity to 4,5,6,7-tetrabromo- and 4,5,6,7-tetraiodo-1H-benzimidazole derivatives. Eur. J. Med. Chem. 47: 345–350.
Kaplancikli Z.A., G. Turan-Zitouni, G. Revial and K. Guven. 2004. Synthesis and study of antibacterial and antifungal activities of novel 2-[[(benzoxazole/benzimidazole-2-yl)sulfanyl] acetylamino] thiazoles. Arch. Pharm. Res. 27: 1081–1085.
Karpińka M.M., J. Matysiak and A. Niewiadomy. 2011. Synthesis of novel 4-(1H-benzimidazol-2-yl)benzene-1,3-diols and their cytotoxic activity against human cancer cell lines. Arch. Pharm. Res. 34: 1639–1647.
Karpińska M.M., J. Matysiak, A. Niewiadomy, J. Wietrzyk and D. Kłopotowska. 2012. Synthesis and biological activity of novel 4- and 6-(1-alkyl/aryl-1H-benzimidazol-2-yl)benzene-1,3-diols Monatshefte für Chemie 143: 269–276.
Kazimierczuk Z., M. Andrzejewska, J. Kaustova and V. Klimesova. 2005. Synthesis and antimycobacterial activity of 2-substituted halogenobenzimidazoles. Eur. J. Med. Chem. 40: 203–208.
Küçükbay H., R. Durmaz, N. Okyucu and S. Günal. 2003a. Antifungal activity of some bis-5-methylbenzimidazole compounds. Folia Microbiol (Praha) 48: 679–681.
Küçükbay H., R. Durmaz, E. Orhan and S. Günal. 2003b. Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds. Farmaco 58: 431–437.
Laudy A.E., R. Moo-Puc, R. Cedillo‐Rivera, Z. Kazimierczuk and A. Orzeszko. 2012. Synthesis and antimicrobial activities of new polyhalogenated benzimidazoles. Journal of Heterocyclic Chemistry 49: 1059–1063.
Los R., M. Wesołowska-Trojanowska, A.M. Malm, M. Karpińska, J. Matysiak, A. Niewiadomy and U. Głaszcz. 2012. A new approach to the synthesis of 2-aryl-substituted benzimidazoles, quinazolines, and other related compounds and their antibacterial activity. Heteroatom Chemistry 23:265–275.
Martin R.J. 1997. Modes of action of anthelmintic drugs. Vet. J. 154: 11–34.
Navarrete-Vázquez G., M.e.M. Rojano-Vilchis, L. Yépez-Mulia, V. Meléndez, L. Gerena, A. Hernández-Campos, R. Castillo and F. Hernández-Luis. 2006. Synthesis and antiprotozoal activity of some 2-(trifluoromethyl)-1H-benzimidazole bioisosteres. Eur. J. Med. Chem. 41:135–141.
Padmavathi V., P. Thriveni, G. Sudhakar Reddy and D. Deepti. 2008. Synthesis and antimicrobial activity of novel sulfone-linked bis heterocycles. Eur. J. Med. Chem. 43: 917–924.
Pagano M.A., M. Andrzejewska, M. Ruzzene, S. Sarno, L. Cesaro, J. Bain, M. Elliott, F. Meggio, Z. Kazimierczuk and others. 2004. Optimization of protein kinase CK2 inhibitors derived from 4,5,6,7-tetrabromobenzimidazole. J. Med .Chem. 47: 6239–6247.
Pedini M., G. Alunni Bistocchi, A. Ricci, L. Bastianini and E. Lepri. 1994. New heterocyclic derivatives of benzimidazole with germicidal activity-XII--Synthesis of N1-glycosyl-2-furyl benzimidazoles. Farmaco 49: 823–827.
Sharma S., S. Gangal and A. Rauf. 2009. Convenient one-pot synthesis of novel 2-substituted benzimidazoles, tetrahydrobenzimidazoles and imidazoles and evaluation of their in vitro antibacterial and antifungal activities. Eur. J. Med. Chem. 44: 1751–1757.
Shingalapur R.V., K.M. Hosamani and R.S. Keri. 2009. Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles. Eur. J. Med. Chem. 44: 4244–4248.
Tunçbilek M., T. Kiper and N. Altanlar. 2009. Synthesis and in vitro antimicrobial activity of some novel substituted benzimidazole derivatives having potent activity against MRSA. Eur. J. Med. Chem. 44: 1024–1033.
Vinodkumar R., S.D. Vaidya, B.V. Siva Kumar, U.N. Bhise, S.B. Bhirud and U.C. Mashelkar. 2008. Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted- 2-(4-phenylethynyl-phenyl)-1H-benzimidazoles and N-substituted 2[4-(4,4-dimethyl-thioc hroman-6-yl-ethynyl)-phenyl)-1H-benzimidazoles. Eur. J. Med. Chem. 43: 986–995.
Zacny V.L., E. Gershburg, M.G. Davis, K.K. Biron and J.S. Pagano. 1999. Inhibition of Epstein-Barr virus replication by a benzimidazole L-riboside: novel antiviral mechanism of 5, 6-dichloro- 2-(isopropylamino)-1-beta-L-ribofuranosyl-1H-benzimidazole. J. Virol. 73: 7271–7277.