161468-52-6

Basic information

• Product Name: ETHYL 6-BROMO-2-OXO-2,3-DIHYDRO-1H-1,3-BENZIMIDAZOLE-1-CARBOXYLATE
• Synonyms: ETHYL 6-BROMO-2-OXO-2,3-DIHYDRO-1H-1,3-BENZIMIDAZOLE-1-CARBOXYLATE
• CAS NO: 161468-52-6
• Molecular Formula: C₁₀H₉BrN₂O₃
• Molecular Weight: 285.09
• Mol File: 161468-52-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.653±0.06 g/cm3(Predicted)
• PKA: 9.60±0.30(Predicted)
• CAS DataBase Reference: ETHYL 6-BROMO-2-OXO-2,3-DIHYDRO-1H-1,3-BENZIMIDAZOLE-1-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 6-BROMO-2-OXO-2,3-DIHYDRO-1H-1,3-BENZIMIDAZOLE-1-CARBOXYLATE(161468-52-6)
• EPA Substance Registry System: ETHYL 6-BROMO-2-OXO-2,3-DIHYDRO-1H-1,3-BENZIMIDAZOLE-1-CARBOXYLATE(161468-52-6)

Safety Data

• Hazardous Substances Data: 161468-52-6(Hazardous Substances Data)

Upstream product

• 41120-23-4 ethyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 

Downstream Products

• 161468-78-6 3-Benzyl-6-bromo-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid ethyl ester 
• 30770-12-8 1-benzyl-5-bromo-1,3-dihydro-benzoimidazol-2-one 
• 396726-00-4 1-benzyl-5-(3-chloro-phenyl)-1,3-dihydro-benzoimidazol-2-one 
• 161469-06-3 1-Benzyl-6-bromo-1,3-dihydro-benzoimidazole-2-one 
• 1027285-95-5 5-Bromo-3-cyclohexylmethyl-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester 
• 396725-94-3 3-Benzyl-5-bromo-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester 
• 339013-60-4 ethyl 6-bromo-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate 

Relevant articles and documents

Rational Design, Pharmacomodulation, and Synthesis of Dual 5-Hydroxytryptamine 7 (5-HT7)/5-Hydroxytryptamine 2A (5-HT2A) Receptor Antagonists and Evaluation by [18F]-PET Imaging in a Primate Brain

We report the synthesis of 46 tertiary amine-bearing N-alkylated benzo[d]imidazol-2(3H)-ones, imidazo[4,5-b]pyridin-2(3H)-ones, imidazo[4,5-c]pyridin-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, oxazolo[4,5-b]pyridin-2(3H)-ones and N,N′-dialkylated benzo[d]imidazol-2(3H)-ones. These compounds were evaluated against 5-HT7R, 5-HT2AR, 5-HT1AR, and 5-HT6R as potent dual 5-HT7/5-HT2A serotonin receptors ligands. A thorough study of the structure-activity relationship of the aromatic rings and their substituents, the alkyl chain length and the tertiary amine was conducted. 1-(4-(4-(4-Fluorobenzoyl)piperidin-1-yl)butyl)-1H-benzo[d]imidazol-2(3H)-one (79) and 1-(6-(4-(4-fluorobenzoyl)piperidin-1-yl)hexyl)-1H-benzo[d]imidazol-2(3H)-one (81) were identified as full antagonist ligands on cyclic adenosine monophosphate (cAMP, KB = 4.9 and 5.9 nM, respectively) and inositol monophosphate (IP1, KB = 0.6 and 16 nM, respectively) signaling pathways of 5-HT7R and 5-HT2AR. Both antagonists crossed the blood-brain barrier as evaluated with [18F] radiolabeled compounds [18F]79 and [18F]81 in a primate's central nervous system using positron emission tomography. Both radioligands showed standard uptake values ranging from 0.8 to 1.1, a good plasmatic stability, and a distribution consistent with 5-HT7R and 5-HT2AR in the CNS.