832102-62-2

Basic information

• Product Name: 1H-Benzimidazole-2,5-diamine, N2-methyl- (9CI)
• Synonyms: 1H-Benzimidazole-2,5-diamine, N2-methyl- (9CI)
• CAS NO: 832102-62-2
• Molecular Formula: C₈H₁₀N₄
• Molecular Weight: 0
• Mol File: 832102-62-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Benzimidazole-2,5-diamine, N2-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-2,5-diamine, N2-methyl- (9CI)(832102-62-2)
• EPA Substance Registry System: 1H-Benzimidazole-2,5-diamine, N2-methyl- (9CI)(832102-62-2)

Safety Data

• Hazardous Substances Data: 832102-62-2(Hazardous Substances Data)

Upstream product

• 74-89-5 methylamine 
• 203302-73-2 2-chloro-1H-benzo[d]imidazol-5-amine 
• 5955-72-6 2-chloro-5-nitro-1H-benzo[d]imidazole 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 4857-06-1 2-chloro-1H-benzoimidazole 

Relevant articles and documents

Fragment Screening Hit Draws Attention to a Novel Transient Pocket Adjacent to the Recognition Site of the tRNA-Modifying Enzyme TGT

Fragment-based lead discovery was applied to tRNA-guanine transglycosylase, an enzyme modifying post-transcriptionally tRNAs in Shigella, the causative agent of shigellosis. TGT inhibition prevents translation of Shigella's virulence factor VirF, hence reducing pathogenicity. One discovered fragment opens a transient subpocket in the preQ1-recognition site by pushing back an aspartate residue. This step is associated with reorganization of further amino acids structurally transforming a loop adjacent to the recognition site by duplicating the volume of the preQ1-recognition pocket. We synthesized 6-carboxamido-, 6-hydrazido-, and 4-guanidino-benzimidazoles to target the opened pocket, including a dihydro-imidazoquinazoline with a propyn-1-yl exit vector pointing into the transient pocket and displacing a conserved water network. MD simulations and hydration-site analysis suggest water displacement to contribute favorably to ligand binding. A cysteine residue, exclusively present in bacterial TGTs, serves as gatekeeper of the transient subpocket. It becomes accessible upon pocket opening for selective covalent attachment of electrophilic ligands in eubacterial TGTs.

Novel benzimidazole-based MCH R1 antagonists

The identification of an MCH R1 antagonist screening hit led to the optimization of a class of benzimidazole-based MCH R1 antagonists. Structure-activity relationships and efforts to optimize pharmacokinetic properties are detailed along with the demonstration of the effectiveness of an MCH R1 antagonist in an animal model of obesity.