63388-37-4

Basic information

• Product Name: Declenperone
• Synonyms: 1-[3-[4-(4-Fluorobenzoyl)piperidino]propyl]-1,3-dihydro-2H-benzimidazol-2-one;R-33204
• CAS NO: 63388-37-4
• Molecular Formula: C₂₂H₂₄FN₃O₂
• Molecular Weight: 381.449
• Mol File: 63388-37-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.226 g/cm³
• Refractive Index: 1.586
• PKA: 12.20±0.30(Predicted)
• CAS DataBase Reference: Declenperone(CAS DataBase Reference)
• NIST Chemistry Reference: Declenperone(63388-37-4)
• EPA Substance Registry System: Declenperone(63388-37-4)

Safety Data

• Hazardous Substances Data: 63388-37-4(Hazardous Substances Data)

Usage

Description

Declenperone is a chemical compound with significant applications in various fields, particularly in pharmaceutical research and development. It is known for its role in the identification of antimalarial drug leads and the development of selective serotonin S2-antagonists.

Uses

Used in Pharmaceutical Industry:
Declenperone is used as a reagent for antimalarial drug lead identification, contributing to the discovery and development of new treatments for malaria.
Declenperone is also used as a chemical component in the development of selective and specific serotonin S2-antagonists, which have potential applications in the treatment of various psychiatric and neurological disorders.

InChI:InChI=1/C22H24FN3O2/c23-18-8-6-16(7-9-18)21(27)17-10-14-25(15-11-17)12-3-13-26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-9,17H,3,10-15H2,(H,24,28)

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 
• 103784-04-9 1-(3-bromopropyl)-1H-benzo[d]imidazol-2(3H)-one 
• 56346-57-7 (4-fluorophenyl)-piperidin-4-ylmethanone 
• 108-10-1 4-methyl-2-pentanone 
• 62780-84-1 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one 

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.