Abstract
1,2-Bis-[2-(5-H/Me/Cl/NO2)-1H-benzimidazolyl]-1,2-ethanediols (L 1–L 4), 1,4-Bis-[2-(5-H/Me/Cl)-1H-benzimidazolyl]-1,2,3,4-butanetetraols (L 5–L 7) and their complexes with FeCl3, CuCl2, and AgNO3 were synthesized; antibacterial activity of the compounds was determined towardStaphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Salmonella typhi, Shigella flexneri, Proteus mirabilis, and antifungal activity againstCandida albicans. The AgI complexes have considerable activity toward the microorganisms. Some AgI complexes show higher activity towardS. epidermidis than AgNO3 and cefuroxime. Cu(L 3)Cl2 and Fe(L 3)Cl3 show an antifungal effect onC. albicans butL 3 itself has no activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Agh-Atabay N.M., Dulger B., Gucin F.: Synthesis and investigation of antimicrobial activity of some bis-benzimidazole-derived chelating agents.Eur.J.Med.Chem. 38, 875–881 (2003).
Akihama S., Takahashi K., Miyajama N.: Antiviral activity of benzimidazole derivatives. IV. Bisbenzimidazole derivatives.Yakugaku Zasshi 94, 247–251 (1974);Chem.Abstr. 81, 9648x (1975).
Altisen M.R.C., Constansa J.F.: Use of 2-(4-(azolylbutyl)piperazinyl-(methyl))-benzimidazole derivatives for treating or preventing asthma.French Pat. Appl. 94 714 766 (1996);Chem.Abstr. 125, P132781q (1996).
Çakir B., Büyükbingöl E., Uçucu Ü., Abbasoğlu U., Noyanalpan N.: Benzimidazole derivatives: Bis-benzimidazoles and their antifungal activities.J.Fac.Pharm.Gazi 5, 71–77 (1988a).
Çakir B., Uçucu Ü., Abbasoğlu U.: Benzimidazole derivatives: 5-chloro-2,2′-bis-benzimidazoles, synthesis, antifungal activities and QSARs.J.Fac.Pharm.Gazi 5, 105–110 (1988b).
Chimirri A., Monforte P., Musumeci L., Rao A., Zappala M., Monforte A.M.: Synthesis and antitumour activity of 1H,3H-thiazolo[3,4-a]benzimidazole derivatives.Arch.Pharm. 334, 203–208 (2001).
Evans D., Hicks T.A., Williamson W.R.N., Dawson W., Meacock S.C.R., Kitchen E.A.: Synthesis of a group of 1H-benzimidazoles and their screening for anti-inflammatory activity.Eur.J.Med.Chem. 31, 635–642 (1996).
Kim S.U., Kim D.Y., Chung G.J., Hong S.K., Sung J., Nam S.H., Lee S.M.: 5-Pyrrolyl-6-halo-2-(pyridiyl-methylsulfinyl)-benzimidazole gastrointestinal ulcer inhibitors.Korean Pat. Appl. 9 432–612 (1996);Chem.Abstr. 125, P114626p (1996).
Klimešová V., Kočí J., Waisser K., Kaustová J.: New benzimidazole derivatives as antimycobacterial agents.Farmaco 57, 259–265 (2002a).
Klimešová V., Koči J., Pour M., Stachel J., Waisser K., Kaustová J.: Synthesis and preliminary evaluation of benzimidazole derivatives as antimicrobial agents.Eur.J.Med.Chem. 37, 409–418 (2002b).
Küçükbay H., Durmaz B.: Antifungal activity of organic and organometallic derivatives of benzimidazole and benzothiazole.Arzneim.Forsch. 47, 667–670 (1997).
Küçükbay H., Durmaz B., N. Okyucu, S. Günal: Antifungal activity of some bis-5-methylbenzimidazole compounds.Folia Microbiol. 48, 679–681 (2003).
National Committee for Clinical Laboratory Standards: Methods for dilutions antimicrobial susceptibility tests for bacteria that grow aerobically. Approved Standard M7-A4, Villanova (USA) 1997a.
National Committee for Clinical Laboratory Standards: Reference method for broth dilution antifungal susceptibility testing of yeasts. Approved Standard M27-A, Villanova (USA) 1997b.
O’Sullivan D.G., Wallis A.K.: New benzimidazole derivatives with powerful protective action on tissue-culture alls infected with types 1, 2, and 3 polio virus.Nature 198, 1270–1273 (1963).
Otaki K., Inoue J., Yamazaki Z., Haya M., Takai Y., Yasue M., Mizuno D.: Screening of antipoliovirus activity of benzimidazole derivatives.Yakugaku Zasshi 85, 926–935 (1965);Chem.Abstr. 64, 2434f (1965).
Rosenfeld D.A., Pratt J.W., Richtmyer N.K., Hudson C.S.: New benzimidazoles from polyhydroxy acids.J.Amer.Chem.Soc. 73, 5907–5908 (1951).
Seth G., Garg Y.: Biologically important coordination compounds of palladium(II) and platinum(IV) with 2-substituted benzimidazole.Asian J. Chem. 14, 1027–1030 (2002).
Sumiyuki A., Katsuo S.T.: Antipolioviral action of 1,2-bis-(2-benzimidazolyl)-1,2-ethanediol derivatives.Meiji Yakka Daigaku Kenkyu Kiyo 4, 25–28 (1974).
Tavman A., Ülküseven B., Agh-Atabay N.M.: 1,2-Bis-(2-benzimidazolyl)-1,2-ethanediol and 1,4-bis-(2-benzimidazolyl)-1,2,3,4-butanetetraol PdCl2 complexes.Transit.Met.Chem. 25, 324–328 (2000).
Tavman A., Ülküseven B., Birteksöz S., Ötuk G.: Antimicrobial activity of some 2- and 3-pyridinyl-1H-benzimidazoles and their FeIII, CuII, ZnII, and AgI complexes.Folia Microbiol. 48, 479–483 (2003).
Ülküseven B., Tavman A., Ötük G., Birteksöz S.: Antimicrobial activity of FeIII, CuII, AgI, ZnII and HgII complexes of 2-(2-hydroxy-5-bromo/nitro-phenyl)-1H- and 2-(2-hydroxyphenyl-5-methyl/chloro/nitro-1H-benzimidazoles).Folia Microbiol. 47, 481–487 (2002).
Author information
Authors and Affiliations
Additional information
This work was supported by the Research Fund ofIstanbul University, project no. 1683/1508 2001.
Rights and permissions
About this article
Cite this article
Tavman, A., Birteksöz, S. & Ötük, G. Antimicrobial activity of 1,2-bis-[2-(5-R)-1H-benzimidazolyl]-1,2-ethanediols, 1,4-bis-[2-(5-R)-1H-benzimidazolyl]-1,2,3,4-butanetetraols and their FeIII, CuII, and AgI complexes. Folia Microbiol 50, 467–472 (2005). https://doi.org/10.1007/BF02931431
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02931431