5-(1-Piperazinyl)benzofuran-2-carboxamide
[CAS# 183288-46-2]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 5-(1-Piperazinyl)benzofuran-2-carboxamide
• Synonyms: 1-(2-Aminocarbonylbenzofuran-5-yl)piperazine
• Molecular Formula: C₁₃H₁₅N₃O₂
• Molecular Weight: 245.28
• CAS Registry Number: 183288-46-2
• SMILES: C1CN(CCN1)C2=CC3=C(C=C2)OC(=C3)C(=O)N

Properties

• Density: 1.268

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

5-(1-Piperazinyl)benzofuran-2-carboxamide is a chemical compound notable for its diverse applications in medicinal chemistry and material science. With the molecular formula C15H15N3O3, this substance features a benzofuran core substituted with a piperazine ring and a carboxamide group, endowing it with a range of useful properties.

The discovery of 5-(1-Piperazinyl)benzofuran-2-carboxamide is rooted in the exploration of benzofuran derivatives and their biological activities. The compound is synthesized through a process involving the reaction of 5-hydroxybenzofuran with a piperazine derivative, followed by the introduction of a carboxamide group. This approach integrates functional groups that are crucial for the compound’s biological activity and chemical reactivity.

In medicinal chemistry, 5-(1-Piperazinyl)benzofuran-2-carboxamide has garnered attention for its potential therapeutic properties. The benzofuran structure is known for its ability to interact with various biological targets, while the piperazine ring enhances the compound’s ability to bind to specific receptors. This combination makes the compound a valuable candidate in drug discovery. It has been studied for its potential as an antitumor, antiviral, or neuroprotective agent. Researchers have explored its ability to modulate biological pathways and develop compounds with improved efficacy and selectivity.

One of the key applications of 5-(1-Piperazinyl)benzofuran-2-carboxamide is in the development of pharmaceuticals. The compound's structure allows it to serve as a lead compound for synthesizing analogs with enhanced pharmacological properties. These analogs are often investigated for their potential to treat various diseases, including cancer and neurodegenerative disorders. The carboxamide group plays a crucial role in forming hydrogen bonds with biological targets, which is important for optimizing binding affinity and specificity.

Additionally, 5-(1-Piperazinyl)benzofuran-2-carboxamide is used in materials science for creating functional materials and chemical probes. Its chemical structure enables it to be incorporated into polymer matrices or used as a building block in the synthesis of advanced materials with tailored properties. The compound's reactivity and functional groups make it suitable for developing materials with specific mechanical, thermal, or electronic properties.

The compound also serves as a valuable tool in chemical research. Its ability to participate in various chemical reactions provides researchers with opportunities to explore new synthesis methods and develop innovative materials. The study of its reaction mechanisms and properties contributes to advancements in organic chemistry and material science.

Overall, 5-(1-Piperazinyl)benzofuran-2-carboxamide is an important compound with significant applications in medicinal chemistry, pharmaceuticals, and materials science. Its unique structure and functional groups enable the development of new therapeutic agents and advanced materials, making it a valuable substance in both industrial and research contexts.

References

2014. Experimental Design Approach for Selective Separation of Vilazodone HCl and Its Degradants by LC-PDA and Characterization of Major Degradants by LC/QTOF–MS/MS. Chromatographia.
DOI: 10.1007/s10337-014-2739-0