142356-40-9

Basic information

• Product Name: 2-BROMO-5,6-DICHLOROBENZIMIDAZOLE
• Synonyms: 2-BROMO-5,6-DICHLOROBENZIMIDAZOLE;1H-Benzimidazole, 2-bromo-5,6-dichloro-;2-bromo-5,6-dichloro-1H-benzo[d]imidazole;2-bromo-5,6-dichloro-1H-1,3-benzodiazole
• CAS NO: 142356-40-9
• Molecular Formula: C₇H₃BrCl₂N₂
• Molecular Weight: 265.92212
• Mol File: 142356-40-9.mol

Chemical Properties

• Boiling Point: 414.8 °C at 760 mmHg
• Flash Point: 204.7 °C
• Appearance: /
• Density: 1.967 g/cm³
• CAS DataBase Reference: 2-BROMO-5,6-DICHLOROBENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-5,6-DICHLOROBENZIMIDAZOLE(142356-40-9)
• EPA Substance Registry System: 2-BROMO-5,6-DICHLOROBENZIMIDAZOLE(142356-40-9)

Safety Data

• Hazardous Substances Data: 142356-40-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-5,6-dichlorobenzimidazole is used as a research compound for the development of new drugs targeting protein kinases. Its potent and selective inhibition of these enzymes makes it a valuable tool in the discovery of novel therapeutic agents for various diseases.
Used in Cancer Treatment:
2-Bromo-5,6-dichlorobenzimidazole is used as an anticancer agent for its ability to interfere with the growth and survival of cancer cells. Its potential applications in cancer treatment are currently being explored, with a focus on understanding its mechanism of action and identifying the specific types of cancer it may be effective against.
Used in Inflammatory and Autoimmune Disease Treatment:
2-Bromo-5,6-dichlorobenzimidazole is used as a therapeutic agent for the treatment of inflammatory and autoimmune diseases. Its ability to regulate immune responses makes it a promising candidate for the development of new treatments for conditions such as rheumatoid arthritis, lupus, and other autoimmune disorders.
Used in Medicinal Chemistry Research:
2-Bromo-5,6-dichlorobenzimidazole is used as a starting point for the synthesis of new compounds with potential therapeutic applications. Its unique chemical structure and biological activities provide a foundation for the design and development of novel drugs with improved efficacy and selectivity.

Upstream product

• 19462-98-7 5,6-dichloro-2,3-dihydro-1H-1,3-benzodiazole-2-thione 
• 6641-64-1 4,5-dichloro-2-nitroaniline 
• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 18672-03-2 2-amino-5,6-dichlorobenzimidazole 

Downstream Products

• 217951-42-3 2-Bromo-5,6-dichloro-1-(a-D-lyxopyranosyl)benzimidazole 
• 142356-43-2 2-bromo-5,6-dichloro-1-β-D-ribofuranosylbenzimidazole 
• 226703-47-5 2-bromo-5,6-dichloro-1-(3,5-di-O-benzoyl-β-L-xylofuranosyl)benzimidazole 
• 176161-24-3 5,6-dichloro-2-isopropylamino-1-(β-L-lyxofuranosyl)benzimidazole 
• 268566-65-0 Thiocarbonic acid O-[(2S,3S,3aS,9aS)-2-(5,6-dichloro-2-cyclopentylamino-benzoimidazol-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-phenyl ester 
• 226703-38-4 2bromo-5,6-dichloro-1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)benzimidazole 

Relevant articles and documents

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.

NOVEL BENZIMIDAZOLE DERIVATIVES AS KINASE INHIBITORS

The present invention relates to derivatives of benzimidazoles of formula (I) as disclosed herein as well as pharmaceutical compositions comprising said derivatives. The derivates according to the present invention are serine/threonine and tyrosine kinase-inhibitors, particularly of PIM1-3-and DYRK1A-kinases and may particularly be used in the treatment of diseases linked to these kinases, such as e.g. leukemias, lymphomas, solid tumors and autoimmune disorders.

Synthesis and in vitro antimicrobial activity of some novel substituted benzimidazole derivatives having potent activity against MRSA

The novel benzimidazole derivatives (3, 5, 8, 9, 12-14, 18-41) were prepared in this paper and the antimicrobial activities of these compounds against Staphylococcus aureus, methicillin-resistant S. aureus (MRSA, standard and clinical isolates), Bacillus subtilis, Escherichia coli and Candida albicans were evaluated. Compounds 24-26 which have no substitution of N-1 position displayed better antibacterial activities than those of standards (ciprofloxacin, ampicillin and sultamicillin) against both the drug-resistant bacteria (MRSA, standard and clinical isolates). These derivatives (24-26), 2,5,6-trihalogenobenzimidazole analogues (8, 12), 5,6-dichloro-2-amino derivative (13), and 5-chloro-2-(4-benzyloxyphenyl)benzimidazole (35) exhibited the most potent antibacterial activity with MIC 3.12 μg/ml against S. aureus.

Process for preparing substituted benzimidazole compounds

The invention relates to new methods of preparing substituted benzimidazole compounds, such as 2-bromo-5,6-dichlorobenzimidazole, which are useful in the preparation of compounds having antiviral activity.

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.

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).

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