Talampanel

Base Information

• Chemical Name: Talampanel
• CAS No.: 161832-65-1
• Molecular Formula: C19H19N3O3
• Molecular Weight: 337.378
• European Community (EC) Number: 803-174-3
• NSC Number: 729898
• UNII: CVS43XG1L5
• DSSTox Substance ID: DTXSID10167259
• Nikkaji Number: J722.092H
• Wikipedia: Talampanel
• Wikidata: Q7678869
• NCI Thesaurus Code: C38139
• Metabolomics Workbench ID: 68277
• ChEMBL ID: CHEMBL61872
• Mol file: 161832-65-1.mol

Synonyms:(R)-7-acetyl-5-(4-aminophenyl)-8,9-dihydro-8-methyl-7H-1,3-dioxolo(4,5-h)benzodiazepine;1-(4'-aminophenyl)-3-acetyl-4-methyl-3,4-dihydro-7,8-methylenedioxy-5H-2,3-benzodiazepine;7-acetyl-5-(4-aminophenyl)-8,9-dihydro-8-methyl-7H-1,3-dioxolo(4,5-h)benzodiazepine;GYKI 53405;GYKI 53773;GYKI-53405;GYKI-53773;GYKI53773;LY 300164;LY-300164;LY300164;talampanel

Chemical Property of Talampanel

Chemical Property:

• Vapor Pressure: 2.84E-11mmHg at 25°C
• Melting Point: 169-172°
• Refractive Index: 1.674
• Boiling Point: 528.9 °C at 760 mmHg
• PKA: 4.67±0.10(Predicted)
• Flash Point: 273.7 °C
• PSA: 77.15000
• Density: 1.37 g/cm³
• LogP: 2.49770
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble15mg/mL, clear
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 337.14264148
• Heavy Atom Count: 25
• Complexity: 544

Purity/Quality:

98%Min ^*data from raw suppliers

Talampanel ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 25-50/53
• Safety Statements: 45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=CC3=C(C=C2C(=NN1C(=O)C)C4=CC=C(C=C4)N)OCO3
• Isomeric SMILES: C[C@@H]1CC2=CC3=C(C=C2C(=NN1C(=O)C)C4=CC=C(C=C4)N)OCO3
• Recent ClinicalTrials: Safety and Efficacy of Talampanel in Glioblastoma Multiforme
• Recent EU Clinical Trials: A Multinational, Multicenter, Randomized, Double-Blind, Placebo-Controlled, Parallel-Group Study to Assess the Efficacy, Tolerability and Safety of talampanel in Subjects with Amyotrophic Lateral Sclerosis (ALS)
• Uses: Talampanel is a potent and selective AMPA antagonist and is also used as an antiepileptic drug.

Technology Process of Talampanel

There total 10 articles about Talampanel 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: 87.0%

(R)-7-acetyl-8,9-dihydro-8-methyl-5-(4-nitrophenyl)-7H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine (161832-64-0) → (8R)-7-acetyl-5-(4-aminophenyl)-8,9-dihydro-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine (161832-65-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1021/ja00154a048

Reference yield:

(5RS,7S)-7,8-dihydro-7-methyl-5-(4-nitrophenyl)-5H-1,3-dioxolo[4,5-G][2]benzopyran-5-ol (196303-02-3) → (8R)-7-acetyl-5-(4-aminophenyl)-8,9-dihydro-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine (161832-65-1)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / ethanol

2: Et₃N / CH₂Cl₂

3: NaOH / ethanol

4: KO₂CH / Pd/C / propan-2-ol

With hydrogenchloride; sodium hydroxide; potassium formate; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; isopropyl alcohol;

DOI:10.1016/S0960-894X(99)00315-7

Reference yield:

(S)-acetic acid-[[6-(2-hydroxypropyl)-1,3-benzodioxol-5-yl](4-nitrophenyl)methylene]hydrazide (196303-03-4) → (8R)-7-acetyl-5-(4-aminophenyl)-8,9-dihydro-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine (161832-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂

2: NaOH / ethanol

3: KO₂CH / Pd/C / propan-2-ol

With sodium hydroxide; potassium formate; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; isopropyl alcohol;

DOI:10.1016/S0960-894X(99)00315-7

upstream raw materials:

(R)-7-acetyl-8,9-dihydro-8-methyl-5-(4-nitrophenyl)-7H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine

(5RS,7S)-7,8-dihydro-7-methyl-5-(4-nitrophenyl)-5H-1,3-dioxolo[4,5-G][2]benzopyran-5-ol

(S)-acetic acid-[[6-(2-hydroxypropyl)-1,3-benzodioxol-5-yl](4-nitrophenyl)methylene]hydrazide

(S)-acetic acid[[6-[2-[(methylsulfonyl)oxy]propyl]-1,3-benzodioxol-5-yl](4-nitrophenyl)methylene]hydrazide

Refernces

• 1、 -. "Crystalline form of dihydro-2,3-benzodiazepine derivative". . . Retrieved 2008/06/13.
• 2、 Anderson, Benjamin A.,Harn, Nancy K.,Hansen, Marvin M.,Harkness, Allen R.,Lodge, David,Leander, J. David. "Synthesis and anticonvulsant activity of 3-aryl-5H-2,3-benzodiazepine AMPA antagonists". . p. 1953 - 1956. Retrieved 2007/10/03.