142372-26-7

Basic information

• Product Name: 1-benzyl-2,5,6-trichlorobenzimidazole
• Synonyms: 1-benzyl-2,5,6-trichlorobenzimidazole
• CAS NO: 142372-26-7
• Molecular Weight: 311.598
• Mol File: 142372-26-7.mol

Chemical Properties

• CAS DataBase Reference: 1-benzyl-2,5,6-trichlorobenzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-2,5,6-trichlorobenzimidazole(142372-26-7)
• EPA Substance Registry System: 1-benzyl-2,5,6-trichlorobenzimidazole(142372-26-7)

Safety Data

• Hazardous Substances Data: 142372-26-7(Hazardous Substances Data)

Upstream product

• 7732-18-5 water 
• 100-39-0 benzyl bromide 
• 584-08-7 potassium carbonate 
• 16865-11-5 2,5,6-trichloro-1H-benzo[d]imidazole 
• 2033-29-6 5,6-dichloro-1,3-dihydrobenzoimidazol-2-one 
• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 

Relevant articles and documents

Design, synthesis, and antiviral evaluations of 1-(substituted benzyl)- 2-substituted-5,6-dichlorobenzimidazoles as nonnucleoside analogues of 2,5,6- trichloro-1-(β-D-ribofuranosyl)benzimidazole

We have recently reported that certain ribosylated polyhalogenated benzimidazoles are potent and selective inhibitors of HCMV replication at noncytotoxic concentrations. To extend the structure-activity relationship beyond these first-generation compounds, we alkylated 5,6dichloro-2- substituted-benzimidazoles with either a series of substituted benzyl halides or (2bromoethyl)benzene to obtain five series of nonnucleoside analogues. Evaluation of these compounds for activity against herpes viruses revealed that the new compounds were less active than the benzimidazole ribonucleosides against human cytomegalovirus (HCMV) and inactive against herpes simplex virus type 1 (HSV-1). However, as part of our broader antiviral testing, we found that some of these compounds were active against HIV. Comparisons of the biological data revealed that a chloro or bromo group was required at the 2-position for the best separation of activity against HIV and cytotoxicity. Evaluation of the most active compounds against drug- resistant HIV suggested that they act by a mechanism other than inhibition of reverse transcriptase.

New 2-piperazinylbenzimidazole derivatives as 5-HT3 antagonists. Synthesis and pharmacological evaluation

A series of 2-piperazinylbenzimidazole derivatives were prepared and evaluated as 5-HT3 receptor antagonists. Their 5-HT3 receptor affinities were evaluated by radioligand binding assays, and their abilities to inhibit the 5-HT-induced Bezold-Jarisch reflex in anesthetized rats were determined. Compound 7e (lerisetron, pK(i) = 9.2) exhibited higher affinity for the 5- HT3 receptor than did tropisetron and granisetron, while compound 7q (pK(i) = 7.5) had very low affinity for this receptor, showing that substitution on the N1 atom of the benzimidazole ring is essential for affinity and activity. The effect of substitution on the aromatic ring of benzimidazole by several substituents in different positions is also discussed. A strong correlation between the 5-HT3 antagonistic activity of the studied compounds and the position of substitution on the aromatic ring was established. Thus, while the 4-methoxy derivative 7m showed weak affinity for the 5-HT3 receptor (pK(i) = 6.7), the 7-methoxy derivative 7n exhibited the highest affinity (pK(i) = 9.4). Compounds 7e and 7n are now under further investigation as drugs for the treatment of nausea and emesis evoked by cancer chemotherapy and radiation.

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).