163521-20-8

Basic information

• Product Name: Vilazodone
• Synonyms: Ethyl 5-(piperazin-1-yl)benzofuran-2-carboxylate;Vilazodone Key interMediates;2-Benzofurancarboxylic acid,5-(1-piperazinyl)-,ethyl ester;5-(1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester;5-(1-Piperazinyl)-2-benzofurancarboxylic Acid Ethyl Ester;Eehyl 5-(piperazin-1-yl)benzofuran-2-carboxylate;Ethyl 5-(PiperaziN-1-Yl-1-BenzofuraN-2-Carboxylate
• CAS NO: 163521-20-8
• Molecular Formula: C15H18N2O3
• Molecular Weight: 274.32
• EINECS: 1806241-263-5
• Mol File: 163521-20-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 429 °C at 760 mmHg
• Flash Point: 213.3 °C
• Appearance: /
• Density: 1.197 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• Solubility: DMSO, Methanol
• PKA: 8.85±0.10(Predicted)
• CAS DataBase Reference: Vilazodone(CAS DataBase Reference)
• NIST Chemistry Reference: Vilazodone(163521-20-8)
• EPA Substance Registry System: Vilazodone(163521-20-8)

Safety Data

• Hazardous Substances Data: 163521-20-8(Hazardous Substances Data)

Usage

Description

Vilazodone, also known as 5-(1-Piperazinyl)-2-benzofurancarboxylic Acid Ethyl Ester, is a chemical compound with a benzofuran structure. It is primarily recognized for its pharmaceutical applications, particularly in the treatment of mental health disorders. Vilazodone exhibits a unique mechanism of action, targeting both serotonin reuptake inhibition and partial agonist activity at the 5-HT1A receptor, making it a valuable compound in the realm of psychopharmacology.

Uses

Used in Pharmaceutical Industry:
Vilazodone is used as an antidepressant medication for the treatment of major depressive disorder (MDD). It works by increasing the levels of serotonin in the brain, which helps to improve mood, reduce anxiety, and alleviate other symptoms associated with depression. The dual mechanism of action at the 5-HT1A receptor and serotonin reuptake inhibition contributes to its effectiveness in managing depressive symptoms.
Additionally, Vilazodone is used as a research compound for the synthesis of benzofuran derivatives. These derivatives have potential applications in the development of new drugs targeting various diseases, including mycobacterium tuberculosis DNA GyrB inhibition. This highlights the versatility of Vilazodone as a starting material in the synthesis of novel compounds with potential therapeutic benefits.

Upstream product

• 334-22-5 N,N-bis(chloro-2-ethyl)amine 
• 174775-48-5 ethyl 5-amino-1-benzofuran-2-carboxylate 
• 90-02-8 salicylaldehyde 
• 97-51-8 5-Nitrosalicylaldehyde 
• 69604-00-8 ethyl 5-nitrobenzo[d]furan-2-carboxylate 
• 64-17-5 ethanol 
• 105-39-5 chloroacetic acid ethyl ester 
• 56621-48-8 1-(4-hydroxyphenyl)piperazine 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 2725-81-7 6-nitrocoumarin 
• 50396-49-1 3-(2-hydroxy-5-nitrophenyl)acrylic acid 
• 10242-12-3 5-nitrobenzofuran-2-carboxylic acid 

Downstream Products

• 163521-11-7 5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester 

Relevant articles and documents

Design, synthesis, biological evaluation of substituted benzofurans as DNA gyraseB inhibitors of Mycobacterium tuberculosis

DNA gyrase of Mycobacterium tuberculosis (MTB) is a type II topoisomerase and is a well-established and validated target for the development of novel therapeutics. By adapting the medium throughput screening approach, we present the discovery and optimization of ethyl 5-(piperazin-1-yl) benzofuran-2- carboxylate series of mycobacterial DNA gyraseB inhibitors, selected from Birla Institute of Technology and Science (BITS) database chemical library of about 3000 molecules. These compounds were tested for their biological activity; the compound 22 emerged as the most active potent lead with an IC50 of 3.2 ± 0.15 μM against Mycobacterium smegmatis DNA gyraseB enzyme and 0.81 ± 0.24 μM in MTB supercoiling activity. Subsequently, the binding of the most active compound to the DNA gyraseB enzyme and its thermal stability was further characterized using differential scanning fluorimetry method.

Synthetic method for vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate

The invention relates to a synthetic method for a vilazodone intermediate, i.e., ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate. The key vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate as shown in a formula I is prepared with 6-nitrocoumarin as a starting raw material through addition, ring opening, intramolecular ring closure, nitro reduction, piperazine ring preparation, etc. The synthetic method is simple in synthetic route, high in the yield of target products and suitable for industrial scale-up production.

A 5 - (piperazin-1-yl) benzofuran-2-carboxylic acid ethyl ester synthesis method

The invention discloses a synthesis method of 5-(piperazin-1-yl) benzofuran-2-carboxylic acid ethyl ester. The synthesis method comprises the following steps: (1) under the protection of nitrogen, adding zinc powder and tetrahydrofuran to a reactor, dropwise adding TiCl4, adding 2-hydroxyl-5-(piperazin-1-yl) benzaldehyden and glyoxal, and rectifying to obtain 3-[2-hydroxyl-5-(piperazin-1-yl)] phenyl-2-acrylic aldehyde; (2) adding a sodium hydroxide solution and a copper sulfate solution to the reactor, and adding the 3-[2-hydroxyl-5-(piperazin-1-yl)] phenyl-2-acrylic aldehyde while stirring to obtain 3-[2-hydroxyl-5-(piperazin-1-yl)] phenyl-2-acrylic acid; (3) dissolving the 3-[2-hydroxyl-5-(piperazin-1-yl)] phenyl-2-acrylic acid in absolute ethyl alcohol and adding to the reactor, and adding tetrahydrofuran and anhydrous potassium carbonate to obtain the 5-(piperazin-1-yl) benzofuran-2-carboxylic acid ethyl ester. The synthesis route disclosed by the invention is wide in raw material source, simple to operate and outstanding in advantage.