99840-45-6

Usage

Chemical family

Benzimidazole

Biological and pharmacological properties

Diverse range

Potential use

Antiparasitic and antiviral agent, effect on the central nervous system

Unique feature

Chemical structure and properties

Subject of interest

Further research and potential applications in medicine and pharmaceuticals.

Upstream product

• 107-92-6 butyric acid 
• 2687-25-4 3-methyl-1,2-benzenediamine 
• 109-74-0 propyl cyanide 
• 2208-08-4 ethyl butyrimidate hydrochloride 
• 123-72-8 butyraldehyde 
• 102-82-9 tributyl-amine 
• 106-31-0 butanoic acid anhydride 

Downstream Products

• 154352-37-1 4-Methyl-2-propyl-1-[[2-(2-cyanophenyl)-5-pyridinyl]methyl]-1H-benzimidazole 
• 1207604-07-6 C₂₀H₂₁N₃O 
• 1207604-02-1 1-(4-iodobenzyl)-4-methyl-2-propyl-1H-benzo[d]imidazole 
• 1207603-95-9 ethyl 2-methyl-2-(4-((4-methyl-2-propyl-1H-benzo[d]imidazol-1-yl)methyl)phenoxy)propanoate 
• 1207603-94-8 C₂₂H₂₆N₂O₃ 

Relevant academic research and scientific papers

Rhodium catalyzed 2-alkyl-benzimidazoles synthesis from benzene-1,2-diamines and tertiary alkylamines as alkylating agents

Substituted 2-alkyl-benzimidazoles were synthesized from benzene-1,2-diamine and tertiary amines as alkylating agent under polystyrene supported rhodium (Rh@PS) nanoparticles (NPs) catalyzed conditions. The heterogeneous rhodium catalyst was applied first time for the synthesis of 2-alkyl-benzimidazoles. The reaction followed through oxidation of alkylamines, transamination, and oxidative cyclisation with benzene-1,2-diamines for the corresponding products synthesis with good yields. The process is applicable for vast substrate scope, several functional groups are tolerable, and the Rh@PS catalyst is recyclable up to four cycles without significant loss in catalytic activity.

Overcoming imatinib resistance in chronic myelogenous leukemia cells using non-cytotoxic cell death modulators

Recent studies examined the possibility to overcome imatinib resistance in chronic myeloid leukemia (CML) patients by combination therapy with peroxisome proliferator-activated receptor gamma (PPARγ) ligands. Pioglitazone, a full PPARγ agonist, improved the survival of patients by the gradual elimination of the residual CML stem cell pool. To evaluate the importance of the pharmacological profile of PPARγ agonists on the ability to circumvent resistance, the partial PPARγ agonist 4‘-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1’-biphenyl]-2-carboxylic acid, derived from telmisartan, and other related derivatives were investigated. The 4-substituted benzimidazole derivatives bearing a [1,1′-biphenyl]-2-carboxamide moiety sensitized K562-resistant cells to imatinib treatment. Especially the derivatives 18a-f, which did not activate PPARγ to more than 40% at 10 μM, retrieved the cytotoxicity of imatinib in these cells. The cell death modulating properties were higher than that of pioglitazone. It is of interest to note that all novel compounds were not cytotoxic neither on non-resistant nor on resistant cells. They exerted antitumor potency only in combination with imatinib.

A highly efficient oxidative condensation reaction for selective protein conjugation

We hereby report a mild and efficient coupling reaction between alkyl aldehydes and aryl diamines. In the presence of a Cu2+ or a Zn 2+ ion, oxygen (O2) in air is able to promote the oxidative condensation of the two readily preparable functional groups, forming stable benzimidazole linkages in neutral aqueous solution at room temperature (RT). We demonstrated that the reaction could be utilized to label a T4 lysozyme protein containing a chemically installed aryl diamine group with a fluorescent aldehyde dye molecule at 37 °C. the Partner Organisations 2014.

Design, synthesis, and docking studies of novel benzimidazoles for the treatment of metabolic syndrome

In addition to lowering blood pressure, telmisartan, an angiotensin (AT1) receptor blocker, has recently been shown to exert pleiotropic effects as a partial agonist of nuclear peroxisome proliferator-activated receptor γ (PPARγ). On the basis of these findings and docking pose similarity between telmisartan and rosiglitazone in PPARγ active site, two classes of benzimidazole derivatives were designed and synthesized as dual PPARγ agonist/angiotensin II antagonists for the possible treatment of metabolic syndrome. Compound 4, a bisbenzimidazole derivative showed the best affinity for the AT1 receptor with a Ki=13.4 nM, but it was devoid of PPARγ activity. On the other hand 9, a monobenzimidazole derivative, showed the highest activity in PPARγ transactivation assay (69% activation) with no affinity for the AT1 receptor. Docking studies lead to the designing of a molecule with dual activity, 10, with moderate PPARγ activity (29%) and affinity for the AT1 receptor (Ki=2.5 μM).

Indolyl-substituted phenylacetic acid derivatives

The indolyl-substituted phenylacetic acid derivatives are prepared by reacting the corresponding phenylacetic acids with the required amines. The indolyl-substituted phenylacetic acid derivatives are suitable as active compounds in medicaments, in particu

Substituted benzimidazoles as angiotensin II antagonists

There are disclosed new substituted benzimidazole compounds and derivatives thereof which are useful as angiotensin II antagonists. These compounds have the general formula: