3-Chloro-5H-pyrrolo[2,3-b]pyrazine
[CAS# 1111638-10-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 3-Chloro-5H-pyrrolo[2,3-b]pyrazine
• Molecular Formula: C₆H₄ClN₃
• Molecular Weight: 153.57
• CAS Registry Number: 1111638-10-8
• SMILES: C1=CNC2=NC(=CN=C21)Cl

Properties

• Density: 1.531

Safety Data

• Hazard Symbols: GHS07 Warnig
• Hazard Statements: H302-H317
• Precautionary Statements: P280

Discovory and Applicatios

3-Chloro-5H-pyrrolo[2,3-b]pyrazine is a heterocyclic compound that has attracted much attention in the field of medicinal chemistry. This compound belongs to the pyrrolopyrazine family, which is characterized by a fused ring structure combining pyrrole and pyrazine moieties. The discovery of 3-chloro-5H-pyrrolo[2,3-b]pyrazine can be traced back to research aimed at developing novel bioactive molecules with potential therapeutic applications.

The synthesis of 3-chloro-5H-pyrrolo[2,3-b]pyrazine generally involves a cyclization reaction starting from an appropriate precursor. A common method involves condensation of 2-chloro-3-nitropyrazine with an appropriate pyrrole derivative, followed by reduction and cyclization steps to form the desired fused ring system. This synthetic route allows the introduction of a chlorine atom at the 3-position, which is a key feature of this compound.

3-Chloro-5H-pyrrolo[2,3-b]pyrazine shows good prospects in various pharmaceutical applications due to its unique structural features and biological activities. Its fused heterocyclic structure is favorable for interaction with various biological targets, making it a valuable scaffold for drug discovery.

Studies have shown that derivatives of 3-chloro-5H-pyrrolo[2,3-b]pyrazine exhibit cytotoxic activity against certain cancer cell lines. This has led to the exploration of these compounds as potential anticancer agents, particularly due to their ability to inhibit key enzymes or pathways involved in cancer cell proliferation.

The antibacterial and antifungal properties of 3-chloro-5H-pyrrolo[2,3-b]pyrazine derivatives have also been investigated. These compounds have shown activity against various strains of microorganisms, suggesting that they could be used to treat infections caused by drug-resistant bacteria and fungi.

Several studies have explored the potential of 3-chloro-5H-pyrrolo[2,3-b]pyrazine derivatives in modulating neural pathways, providing the possibility that these compounds could be developed as therapeutic agents for central nervous system disorders, including neurodegenerative and psychiatric disorders.

The unique chemical properties and biological activities of 3-chloro-5H-pyrrolo[2,3-b]pyrazine continue to drive medicinal chemistry research. Future research may focus on optimizing the pharmacokinetic and pharmacodynamic properties of these compounds to enhance their efficacy and safety. In addition, the development of novel derivatives and analogs could expand their therapeutic potential in a wider range of diseases.