Synthesis, antiprotozoal and antibacterial activity of nitro- and halogeno-substituted benzimidazole derivatives.

• Authors: Zygmunt Kazimierczuk , Jacqueline A Upcroft , Peter Upcroft , Agata Górska , Bohdan Starościak , Agnieszka Laudy
• Languages of publication: EN

Abstracts

EN

Two series of benzimidazole derivatives were sythesised. The first one was based on 5,6-dinitrobenzimidazole, the second one comprises 2-thioalkyl- and thioaryl-substituted modified benzimidazoles. Antibacterial and antiprotozoal activity of the newly obtained compounds was studied. Some thioalkyl derivatives showed remarkable activity against nosocomial strains of Stenotrophomonas malthophilia, and an activity comparable to that of metronidazole against Gram-positive and Gram-negative bacteria. Of the tested compounds, 5,6-dichloro-2-(4-nitrobenzylthio)-benzimidazole showed the most distinct antiprotozoal activity.

Keywords

EN

antibacterial activity; antiprotozoal activity; benzimidazoles

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2002
• Volume: 49
• Issue: 1
• Pages: 185-195

Dates

published

2002

received

2001-09-10

revised

2002-01-21

accepted

2002-02-02

Contributors

author

Zygmunt Kazimierczuk

• Institute of Chemistry, Agricultural University, Warszawa, Poland

author

Jacqueline A Upcroft

• The Queensland Institute of Medical Research, Brisbane, Australia

author

Peter Upcroft

• The Queensland Institute of Medical Research, Brisbane, Australia

author

Agata Górska

• Institute of Chemistry, Agricultural University, Warszawa, Poland

author

Bohdan Starościak

• Medical University, Department of Pharmaceutical Microbiology, Warszawa, Poland

author

Agnieszka Laudy

• Medical University, Department of Pharmaceutical Microbiology, Warszawa, Poland

References

• 1. Sheehan, D.J., Hitchcock, C. A. & Sibley, C.M. (1999) Current and emerging antifungal agents. Clin. Microbiol. Rev. 12, 40-79.
• 2. Habib, N.S., Soliman, R., Ashour, F.A. & el-Taiebi, M. (1997) Synthesis and antimicrobial testing of novel oxadiazolylbenzimidazole derivatives. Pharmazie. 52, 746-749.
• 3. Tuncbilek, M., Goker, H., Ertan, R., Eryigit, R., Kendi, E. & Altanlar E. (1997) Synthesis and antimicrobial activity of some new anilino benzimidazoles. Arch. Pharm. 330, 372-376.
• 4. Pedini, M., Alunni Bistochi, G., Ricci, A., Bastianini, L. & Lepri, E. (1994) New heterocyclic derivatives of benzimidazole with germicidal activity - XII. Synthesis of N1-glycosyl-2-furyl benzimidazoles. Farmaco. 49, 823-827.
• 5. Lackner, T.E. & Clissold, S.P. (1989) Bifonazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses. Drugs. 38, 204-225.
• 6. Devivar, R.V., Kawashima, E., Revankar, G.R., Breitenbach, J., Kreske, E., Drach, J. & Townsend, L. (1994) Benzimidazole ribonucleosides: Design, synthesis, and antiviral activity of certain 2-(alkylthio)- and 2-(benzylthio)-5,6-dichloro-1-(β -D -ribofuranosyl)benzimidazoles. J. Med. Chem. 37, 2942-2949.
• 7. Pawełkiewicz, J. & Zodrow, K. (1957) Prekursory biosyntezy nukleotydocyjanokobalamin. Acta Microbiol. Polon. 6, 9-15 (in Polish).
• 8. Burton, D.E., Lambie, A.J., Ludgate, J.C., Newbold, G.T., Percival, A. & Saggers, D.T. (1965) 2Trifluoromethylbenzimidazoles; a new class of herbicidal compounds. Nature 208, 1166-1170.
• 9. Navarette-Vazquez, G., Cedillo, R., Hernandez-Campos, A., Yepez, L., Hernandez-Luis, F., Valdez, J., Morales, R., Cortes, R., Hernandez, M. & Castillo, R. (2001) Synthesis and antiparasitic activity of 2-(trifluoromethyl)benzimidazole derivatives. Bioorg. Med. Chem. Lett. 11, 187-190.
• 10. Xiao, L., Saeed, K. & Herd, R.P. (1996) Efficacy of albendazole and fenbedazole against Giardia infection in cattle. Vet. Parasitol. 61, 165-170.
• 11. Katiyar, S.K., Gordon, V.R., McLaughlin, G.L. & Edlind, T.D. (1994) Antiprotozoal activities of benzimidazoles and correlations with beta-tubulin sequence. Antimicrob. Agents Chemother. 38, 2086-2090.
• 12. Bishop, B.C., Chelton, E.T.J. & Jones, A.S. (1964) The antibacterial activity of some fluorine-containing benzimidazoles. Biochem. Pharmacol. 13, 751-754.
• 13. Stefańska, J.Z., Gralewska, R., Starościak, B.J. & Kazimierczuk, Z. (1999) Antimicrobial activity of substituted azoles and their nucleosides. Pharmazie. 54, 879-884.
• 14. National Committee for Clinical Laboratory Standards, NCCLS Approval Standard Document M2-A7. (2000) Villanova, PA, U.S.A
• 15. National Committee for Clinical Laboratory Standards, NCCLS Approval Standard Document M7-A5. (2000) Villanova, PA, U.S.A
• 16. Upcroft, J.A. & Upcroft, P. (2001) Drug susceptibility testing of the anaerobic protozoa. Antimicrob. Agents Chemother. 45, 1810-1814.
• 17. Kazimierczuk, Z. & Shugar, D. (1989) Preparation and properties of the 5,6- and 4,6-dinitro derivatives of benzimidazole and their 1-β-D-ribofuranosides. Nucleosides Nucleotides. 8, 1379-1385.
• 18. Bűchel, K.H. (1970) Herbizide Trifluoromethyl-benzimidazole. Z. Naturforsch. 25b, 934-944.
• 19. Jpn. Patent 1097861, through Chem. Abstr (1963) 58, 13964.
• 20. Alonso, A. & Martinez, J.C. (1997) Multiple antibiotic resistance in Stenotrophomonas maltophilia. Antimicrob. Agents Chemother. 41, 1140-1142.