163521-19-5

Basic information

• Product Name: 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid
• Synonyms: 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid;2-Benzofurancarboxylic acid, 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-;Vilazodone Carboxy Acid;Vilazodone Carboxylic acid
• CAS NO: 163521-19-5
• Molecular Formula: C₂₆H₂₆N₄O₃
• Molecular Weight: 443
• Mol File: 163521-19-5.mol

Chemical Properties

• Melting Point: 189-192 °C
• Boiling Point: 717.9±60.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Heated)
• PKA: 15.98±0.30(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid(163521-19-5)
• EPA Substance Registry System: 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid(163521-19-5)

Safety Data

• Hazardous Substances Data: 163521-19-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential applications in treating a range of medical conditions.
Used in Antidepressant Development:
5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid is used as a key intermediate in the preparation of antidepressant medications. Its chemical structure contributes to the development of novel antidepressants with improved efficacy and reduced side effects.
Used in Drug Synthesis:
In the field of drug synthesis, 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid serves as a valuable building block for the creation of new drug candidates. Its versatile chemical properties enable the design of innovative therapeutic agents with potential applications in various medical fields.
Used in Chemical Research:
5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid is also utilized in chemical research for studying the properties and reactivity of complex organic molecules. 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid can provide insights into the development of new synthetic methods and the understanding of molecular interactions in various chemical processes.

Upstream product

• 15861-24-2 1H-indole-5-carbonitrile 
• 143612-79-7 3-(4-chlorobutyl)-5-cyanoindole 
• 765935-67-9 5-(1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester hydrochloride 
• 276863-95-7 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile 
• 69604-00-8 ethyl 5-nitrobenzo[d]furan-2-carboxylate 
• 163521-11-7 5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester 
• 174775-48-5 ethyl 5-amino-1-benzofuran-2-carboxylate 

Downstream Products

• 163521-12-8 vilazodone 

Relevant articles and documents

Synthesis and structure-activity relationship in a class of indolebutylpiperazines as dual 5-HT1A receptor agonists and serotonin reuptake inhibitors

Systematic structural modifications of indolealkylphenylpiperazines led to improved selectivity and affinity within this class of 5-HT1A receptor agonists. Introduction of electron-withdrawing groups in position 5 on the indole raises serotonin transporter affinity, and the cyano group proved to be the best substituent here. 5-Fluoro and 5-cyano substituted indoles show comparable results in in vitro and in vivo tests, and bioisosterism between these substituents was supported by calculation of the molecular electrostatic potentials and dipole moments. Compounds showing promising in vitro data were further examined in ex vivo (p-chloroamphetamine assay) and in vivo (ultrasonic vocalization) tests. Optimization of the arylpiperazine moiety indicated that the 5-benzofuranyl-2-carboxamide was best suited to increase 5-HT transporter and 5-HT1A receptor affinity and to suppress D2 receptor binding. 5-{4-[4-(5-Cyano-3-indolyl)butyl]-1-piperazinyl}benzofuran-2- carboxamide 29 (vilazodone, EMD 68843) was identified as a highly selective 5-HT1A receptor agonist [GTPγS, ED50 = 1.1 nM] with subnanomolar 5-HT1A affinity [IC50 = 0.2 nM] and as a subnanomolar 5-HT reuptake inhibitor [RUI = 0.5 nM] showing a great selectivity to other GPCRs (e.g., D2, IC50 = 666 nM).