Esaprazole

Base Information

• Chemical Name: Esaprazole
• CAS No.: 64204-55-3
• Molecular Formula: C12H23 N3 O
• Molecular Weight: 225.33052
• Hs Code.: 2933599090
• UNII: 38QSU0IB5L
• DSSTox Substance ID: DTXSID0046147
• Nikkaji Number: J330.990H
• Wikidata: Q27256807
• NCI Thesaurus Code: C65535
• ChEMBL ID: CHEMBL1983100
• Mol file: 64204-55-3.mol

Synonyms:esaprazole;esaprazole monohydrochloride;hexaprazol;N-((N-cyclohexylcarbamoyl)methyl)piperazine

Chemical Property of Esaprazole

Chemical Property:

• Vapor Pressure: 3.14E-07mmHg at 25°C
• Melting Point: 111-112°
• Boiling Point: 419°C at 760 mmHg
• PKA: 15.27±0.20(Predicted)
• Flash Point: 207.2°C
• PSA: 44.37000
• Density: 1.07g/cm³
• LogP: 0.99810
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 225.184112366
• Heavy Atom Count: 16
• Complexity: 220

Purity/Quality:

97% ^*data from raw suppliers

N-cyclohexyl-2-piperazin-1-ylacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)NC(=O)CN2CCNCC2

Technology Process of Esaprazole

There total 4 articles about Esaprazole 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: 82.0%

piperazine (110-85-0) + 2-Chloro-N-cyclohexylacetamide (23605-23-4) → N-cyclohexyl-piperazino-acetamide (64204-55-3)

Guidance literature:

With hydrogenchloride; In water; at 100 ℃; for 2h;

Reference yield:

cyclohexylamine (108-91-8,157973-60-9) → N-cyclohexyl-piperazino-acetamide (64204-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) diisopropylcarbodiimide, 4-dimethylaminopyridine, Wang resin, 3.) AlCl₃ / 1.) DMF, 18 h, 2.) DMF, 18 h, 3.) CH₂Cl₂, RT, 18 h

2: CH₂Cl₂; trifluoroacetic acid

With dmap; aluminium trichloride; Wang resin; diisopropyl-carbodiimide; In dichloromethane; trifluoroacetic acid;

DOI:10.1016/0040-4039(96)00498-4

Reference yield:

4-Cyclohexylcarbamoylmethyl-piperazine-1-carboxylic acid tert-butyl ester (177971-60-7) → N-cyclohexyl-piperazino-acetamide (64204-55-3)

Guidance literature:

In dichloromethane; trifluoroacetic acid; Yield given;

DOI:10.1016/0040-4039(96)00498-4

upstream raw materials:

piperazine

2-Chloro-N-cyclohexylacetamide

4-Cyclohexylcarbamoylmethyl-piperazine-1-carboxylic acid tert-butyl ester

cyclohexylamine

Refernces

Synthesis and biological evaluation of Esaprazole analogues showing σ₁ binding and neuroprotective properties in vitro

10.1016/j.bmc.2013.02.058

The research focuses on the synthesis and biological evaluation of Esaprazole analogues, aiming to enhance their neuroprotective properties and blood-brain barrier penetration. Esaprazole, initially known for its protective effects against stomach and intestinal ulcers, was found to exhibit neuroprotective activities and bind to the sigma r1 receptor in vitro. The study prepared a diverse set of Esaprazole analogues to increase their potential to penetrate the blood-brain barrier. These analogues were evaluated for their structure-activity relationship at the r1 receptor and their neuroprotective properties using primary cultures of cortical neurons exposed to glutamate and hydrogen peroxide. The research concluded that while many analogues showed neuroprotective properties, a clear structure-activity relationship could not be established for the neuroprotection assays. However, the metabolic stability and blood-brain barrier penetration of the analogues were significantly influenced by the structure of R1, leading to two distinct series of compounds. The chemicals used in the synthesis process included Esaprazole and various analogues with different R1 substitutions, such as H, acyl, cyclo- or bicyclo-alkyl groups, which affected their ADME (Absorption, Distribution, Metabolism, and Excretion) properties.

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