62908-78-5

Usage

Chemical Class

Benzimidazole

Anti-fungal properties

Strong

Functional Groups

Trichloro, Furanosyl

Mechanism of Action

Interferes with growth and reproduction of fungi

Applications

Agriculture, Veterinary Medicine, Pharmaceuticals

Potential

Valuable tool in combating fungal diseases, further research and development may lead to new treatments.

Upstream product

• 142356-41-0 tri-O-acetyl-1-(2,5,6-trichloro-benzoimidazol-1-yl)-β-D-1-deoxy-ribofuranose 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 16865-11-5 2,5,6-trichloro-1H-benzo[d]imidazole 
• 18672-03-2 2-amino-5,6-dichlorobenzimidazole 
• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 

Downstream Products

• 194159-82-5 2,5,6-trichloro-1-(2,5-di-O-trityl-β-D-ribofuranosyl)benzimidazole 
• 194159-81-4 2,5,6-trichloro-1-(3,5-di-O-trityl-β-D-ribofuranosyl)benzimidazole 
• 194159-83-6 2,5,6-trichloro-1-(3,5-di-O-trityl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)benzimidazole 
• 194159-84-7 2,5,6-trichloro-1-(2,5-di-O-trityl-3-deoxy-3-fluoro-β-D-xylofuranosyl)benzimidazole 

Relevant academic research and scientific papers

BENZIMIDAZOLE DERIVATIVES AND MEDICAL USES THEREOF

The present invention providesbenzimidazole derivatives represented by the following formula (I) or pharmaceutically acceptable salts thereof, or prodrugs thereof, which exert an inhibitory activity on sodium-dependent nucleoside transporter 2 and are useful for a disease associated with an abnormality of plasma uric acid level. The compounds of the present invention are useful for the prevention or treatment of gout, hyperuricemia, urinary lithiasis, hyperuricemic nephropathy or the like. In the formula, n is 1 or 2; R1 and R2 are H, a halogen atom, cyano group, optionally substituted alkyl group, optionally substituted aryl group or the like; R3 is H, a halogen atom, optionally substituted alkyl group or the like; R9 and R5 are H, a halogen atom, OH or the like; and R6 and RX are H or OH: RY is F or OH.

Polysubstituted benzimidazoles as antiviral agents

Polysubstituted benzimidazoles and pharmaceutical compositions containing them as the active ingredients. These compounds and compositions exhibit antiviral activity against viruse of the herpes family, particularly human cytomegalovirus and herpes simplex viruses (HSV).

Design, Synthesis, and Antiviral Activity of Certain 2,5,6-Trihalo-1-(β-D-ribofuranosyl)benzimidazoles

A new series of 2-substituted 5,6-dichlorobenzimidazole ribonucleosides has been synthesized and tested for activity against two human herpes viruses and for cytotoxicity. 2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB) was prepared by ribosylation of the heterocycle 2,5,6-trichlorobenzimidazole followed by a removal of the protecting groups.The 2-bromo derivative (BDCRB) was made in a similar fashion from 2-bromo-5,6-dichlorobenzimidazole.In contrast, the 2-iodo derivative presented a more difficult problem since the appropriate heterocycle was unavailable.This prompted us to prepare the 2-amino derivative followed by nonaqueous diazotization and removal of the blocking groups.Biological evaluation revealed marked differences in the activities of these compounds and the closely related known compound 5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (DRB).DRB was weakly active against both human cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1), (IC50's = 42 and 30 μM, respectively) but was cytotoxic to uninfected human foreskin fibroblasts and KB cells in the same dose range.Similar results were obtained with the heterocycle 2,5,6-trichlorobenzimidazole.In marked contrast, the ribonucleoside of 2,5,6-trichlorobenzimidazole (TCRB) was active against HCMV (IC50 = 2.9 μM, plaque assay; IC90 = 1.4 μM, yield assay) but only weakly active against HSV-1 (IC50 = 102 μM, plaque assay).Little to no cytotoxicity was observed in HFF and KB cells at concentrations up to 100 μM.By changing the substituent at the 2-position from chlorine to bromine (BDCRB), a 4-fold increase in activity against HCMV was observed without any significant increase in cytotoxicity.In contrast, the 2-I and 2-NH2 derivatives were only weakly active against HCMV and HSV-1 with activity not well-separated from cytotoxicity.These data establish that for maximum activity against HCMV with separation from cytotoxicity, ribose is preferred at the 1-position and that Cl or Br is apparently preferred at the 2-position.The activity and selectivity of both TCRB and BDCRB were better than that observed with either ganciclovir or foscarnet.

Polysubstituted benzimidazoles as antiviral agents

This invention relates to novel polysubstituted benzimidazoles and compositions and their use in the treatment of viral infections. The polysubstituted benzimidazoles and compositions of the present invention exhibit antiviral properties against viruses of the herpes family, particularly human cytomegalovirus (HCMV) and herpes simplex viruses (HSV). Preferred polysubstituted benzimidazoles of the invention are 2,5,6-Trichloro-1-(β-D-5-deoxyribofuranosyl)benzimidazole and 2-bromo-5,6-dichloro-1-(5-deoxy-β-D-ribofuranosyl)benzimidazole.

Polysubstituted benzimidazole nucleosides as antiviral agents

This invention relates to novel polysubstituted benzimidazole nucleosides and compositions and their use in the treatment of viral infections, particulary those caused by human cytomegalovirus and herpes simplex virus. Such substituted compounds exhibit a