Synthesis, antiprotozoal and anticancer activity of substituted 2-trifluoromethyl- and 2-pentafluoroethylbenzimidazoles.

The synthesis of several halogenated benzimidazoles substituted in position 2 with trifluoromethyl, pentafluoroethyl and 2-thioethylaminodimethyl group is reported. Antiprotozoal and anticancer activity of series of newly synthesized and previously obtained compounds was studied. All of tested bezimidazoles showed remarkable antiprotozoal activity against Giardia intestinalis, Entamoeba histolytica and Trichomonas vaginalis. Of the studied collection of halogenated benzimidazoles the most anticancer-active was the 5,6-dichloro-2-pentafluoroethyl compound, particularly against breast and prostate cancer cell lines.

[1]  R. Castillo,et al.  Synthesis and antiparasitic activity of 2-(trifluoromethyl)-benzimidazole derivatives. , 2001, Bioorganic & medicinal chemistry letters.

[2]  T. Lackner,et al.  Bifonazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses. , 1989, Drugs.

[3]  O. Muñoz,et al.  In-vitro susceptibility of Giardia lamblia to albendazole, mebendazole and other chemotherapeutic agents. , 1992, Journal of medical microbiology.

[4]  D. Sheehan,et al.  Current and Emerging Azole Antifungal Agents , 1999, Clinical Microbiology Reviews.

[5]  S. Katiyar,et al.  Antiprotozoal activities of benzimidazoles and correlations with beta-tubulin sequence , 1994, Antimicrobial Agents and Chemotherapy.

[6]  R. Castillo,et al.  Synthesis and antiparasitic activity of 1H-benzimidazole derivatives. , 2002, Bioorganic & medicinal chemistry letters.

[7]  R. Herd,et al.  Efficacy of albendazole and fenbendazole against Giardia infection in cattle. , 1996, Veterinary parasitology.

[8]  M. Tunçbilek,et al.  Synthesis and Antimicrobial Activity of Some New Anilino Benzimidazoles , 1997, Archiv der Pharmazie.

[9]  S. Davies,et al.  Selectivity of 4,5,6,7‐tetrabromobenzotriazole, an ATP site‐directed inhibitor of protein kinase CK2 (‘casein kinase‐2’) , 2001, FEBS letters.

[10]  A. Percival,et al.  2-Trifluoromethylbenzimidazoles: A New Class of Herbicidal Compounds , 1965, Nature.

[11]  E. Lepri,et al.  New heterocyclic derivatives of benzimidazole with germicidal activity--XII--Synthesis of N1-glycosyl-2-furyl benzimidazoles. , 1994, Farmaco.