103784-04-9

Basic information

• Product Name: 1-(3-BroMopropyl)-1,3-dihydro-2H-benziMidazol-2-one
• Synonyms: 1-(3-BroMopropyl)-1,3-dihydro-2H-benziMidazol-2-one
• CAS NO: 103784-04-9
• Molecular Formula: C₁₀H₁₁BrN₂O
• Molecular Weight: 255.11114
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 103784-04-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.506±0.06 g/cm3(Predicted)
• PKA: 12.09±0.30(Predicted)
• CAS DataBase Reference: 1-(3-BroMopropyl)-1,3-dihydro-2H-benziMidazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-BroMopropyl)-1,3-dihydro-2H-benziMidazol-2-one(103784-04-9)
• EPA Substance Registry System: 1-(3-BroMopropyl)-1,3-dihydro-2H-benziMidazol-2-one(103784-04-9)

Safety Data

• Hazardous Substances Data: 103784-04-9(Hazardous Substances Data)

Usage

Uses

1-(3-Bromopropyl)-1,3-dihydro-2H-benzimidazol-2-one is an impurity of Domperidone (D531100), a novel peripheral dopamine receptor antagonist that does not cross the blood-brain barrier and is used as an anti-emetic agent.

Upstream product

• 1148017-48-4 tert-butyl 3-(3-bromopropyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 161468-45-7 tert‐butyl 2‐oxo‐2,3‐dihydro‐1H‐benzo[d]imidazole‐1‐carboxylate 

Downstream Products

• 63388-37-4 Declenperone 
• 103783-79-5 1-[3-[4-[Bis-(4-fluorophenyl)hydroxymethyl]piperidinyl]propyl]-1,3-dihydro-2(2H)-benzimidazolone 

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.