Sonepiprazole

Base Information

• Chemical Name: Sonepiprazole
• CAS No.: 170858-33-0
• Molecular Formula: C21H27 N3 O3 S
• Molecular Weight: 401.53
• UNII: O609V24217
• DSSTox Substance ID: DTXSID801317650
• Nikkaji Number: J751.345C
• Wikipedia: Sonepiprazole
• Wikidata: Q7560929
• NCI Thesaurus Code: C73294
• Pharos Ligand ID: C2SRPRYFQGQQ
• ChEMBL ID: CHEMBL69759
• Mol file: 170858-33-0.mol

Synonyms:4-(4-(2-(3,4-dihydro-1H-2-benzopyran-1-yl)ethyl)-1-piperazinyl)benzenesulfonamide monomethanesulfonate;4-(4-(2-(isochroman-1-yl)ethyl)piperazin-1-yl)benzenesulfonamide;isoChr-EtPip-PhSO2NH2;PNU-101387G;sonepiprazole;U 101387;U-101387

Chemical Property of Sonepiprazole

Chemical Property:

• Vapor Pressure: 5.27E-15mmHg at 25°C
• Boiling Point: 613.9°Cat760mmHg
• Flash Point: 325.1°C
• PSA: 84.25000
• Density: 1.244g/cm³
• LogP: 3.94410
• Storage Temp.: room temp
• Solubility.: DMSO: >10mg/mL
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 401.17731291
• Heavy Atom Count: 28
• Complexity: 593

Purity/Quality:

98%Min ^*data from raw suppliers

Sonepiprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC(C2=CC=CC=C21)CCN3CCN(CC3)C4=CC=C(C=C4)S(=O)(=O)N
• Isomeric SMILES: C1CO[C@H](C2=CC=CC=C21)CCN3CCN(CC3)C4=CC=C(C=C4)S(=O)(=O)N
• Description: Sonepiprazole is a selective antagonist of the dopamine 4 (D4) receptor (Kis = 10 nM). It is highly selective over D1, D2, and D3 receptors, serotonin 1A and 2 receptors, as well as α1- and α2-adrenergic receptors (Kis > 2,000 nM). Its safety profile in rat studies is improved in comparison to classical antipsychotics but it is not effective for positive or negative symptoms of schizophrenia in patients. In a pharmacological model of stress exposure in rhesus monkeys, sonepiprazole reverses stress-induced cognitive deficits.
• Uses: Sonepiprazole is a dopamine D4 antagonist with Ki=10 nM.

Technology Process of Sonepiprazole

There total 6 articles about Sonepiprazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-(piperazin-1-yl)-benzenesulfonamide (170856-87-8) + Methanesulfonic acid (S)-2-isochroman-1-yl-ethyl ester (1026828-66-9) → sonepiprazole (170858-33-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethylene glycol; at 90 ℃;

DOI:10.1021/jm960084f

Reference yield:

2-phenylethanol (60-12-8) → sonepiprazole (170858-33-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / TiCl₄ / CH₂Cl₂

2: aq. NaOH

4: BH₃*Me₂S

5: EtN(i-Pr)2

6: EtN(i-Pr)2 / ethane-1,2-diol / 90 °C

With sodium hydroxide; dimethylsulfide borane complex; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethylene glycol;

DOI:10.1021/jm960084f

Reference yield:

ethyl 2-(isochroman-1-yl)acetate (170856-55-0) → sonepiprazole (170858-33-0)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. NaOH

3: BH₃*Me₂S

4: EtN(i-Pr)2

5: EtN(i-Pr)2 / ethane-1,2-diol / 90 °C

With sodium hydroxide; dimethylsulfide borane complex; N-ethyl-N,N-diisopropylamine; In ethylene glycol;

DOI:10.1021/jm960084f

upstream raw materials:

4-(piperazin-1-yl)-benzenesulfonamide

Methanesulfonic acid (S)-2-isochroman-1-yl-ethyl ester

2-phenylethanol

(isochroman-1-yl)acetic acid