7479-04-1

Usage

Class of compound

Benzimidazole derivative (heterocyclic organic compound)

Appearance

Off-white solid

Molecular weight

204.28 g/mol

Use in industry

Building block for synthesis of various medications and biologically active compounds

Use in research and development

Drug discovery and medicinal chemistry

Potential applications

Treatment of various diseases and conditions

Value in drug development

Chemical properties

InChI:InChI=1/C12H16N2/c1-3-4-5-12-13-10-7-6-9(2)8-11(10)14-12/h6-8H,3-5H2,1-2H3,(H,13,14)

Upstream product

• 496-72-0 4-methyl-1,2-diaminobenzene 
• 109-52-4 valeric acid 
• 13820-09-2 trimethyl orthovalerate 

Downstream Products

• 1393601-38-1 C₁₉H₂₁BrN₂ 
• 1393601-46-1 C₃₄H₄₀N₄O₅S 
• 1393601-31-4 4'-[(2-butyl-6-methyl-1H-benzimidazol-1-yl)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-[1,1'-biphenyl]-2-sulfonamide 
• 133140-32-6 tert.butyl 4'-[(2-n-butyl-5-methyl-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylate 
• 133140-31-5 tert-butyl 4'-[(2-n-butyl-6-methyl-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 4′-[(benzimidazole-1-yl) methyl]biphenyl-2-sulfonamide derivatives as dual angiotensin II/endothelin A receptor antagonists

A series of 4′-[(benzimidazole-1-yl)methyl]biphenyl-2-sulfonamide derivatives (Ia-Il) were synthesized and biologically evaluated. It was found that Ig, the most active compound, antagonized both Ang II AT1 and endothelin ETA receptors (AT1 IC50 = 8.5, ETA IC50 = 8.9 nM), and was more potent than losartan in RHRs with no significant effect on heart rate. The preliminary structure-activity relationships were also discussed in the present paper.

A mild, efficient and one-pot synthesis of 2-substituted benzimidazoles by ZrOCl2. 8H2O catalyzed ring closure reaction

A mild, efficient and one-pot synthesis of an array of 2-substituted benzimidazoles from an appropriate o-phenylenediamine and orthoesters such as orthoformate, orthoacetate and orthovalerate using ZrOCl2-8H 2O, at room temperature and under microwave irradiation is described. Ecofriendly, solvent-free methodology has been employed under microwave condition. Compared with the conventional method, microwave irradiation method has the advantages of excellent yields (81-93%) and shorter reaction time (5-10 min).

A highly effective sulfamic acid/methanol catalytic system for the synthesis of benzimidazole derivatives at room temperature

Sulfamic acid/methanol was found to be an efficient catalytic system for the synthesis of benzimidazole compounds through the condensation of o-phenylenediamine with orthoester in high yields at room temperature.

6-Substituted benzimidazoles as new nonpeptide angiotensin II receptor antagonists: Synthesis, biological activity, and structure-activity relationships

Starting from the recently reported nonpeptidic angiotensin II (AII) receptor antagonists DuP 753 (1) and Exp 7711 (2), we have designed and investigated novel substituted benzimidazoles. Systematic variation of several substituents at the benzimidazole ring positions 4-7 led to the finding that substitution in position 6 with acylamino groups results in highly active AII antagonists. Compounds with 6-membered lactam or sultam substituents in position 6 of benzimidazole showed receptor activities in the low nanomolar range but were only weakly active when given orally to rats. In contrast, analogous substitution of the benzimidazole moiety with basic heterocycles resulted in potent AII antagonists which were also well absorbed after oral application. The most active compound of this series, 33 (BIBR 277), was selected as a candidate for clinical development. On the basis of molecular modeling studies a binding model of this new class of AII antagonists to the AT1 receptor is proposed.