Pyrrolo[1,2-a]pyrazin-1-one
[CAS# 136927-63-4]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: Pyrrolo[1,2-a]pyrazin-1-one
• Synonyms: Pyrrolo[1,2-a]pyrazin-1(2H)-one
• Molecular Formula: C₇H₆N₂O
• Molecular Weight: 134.14
• CAS Registry Number: 136927-63-4
• EC Number: 958-547-4
• SMILES: C1=CN2C=CNC(=O)C2=C1

Properties

• Density: 1.33±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.668, Calc.^*
• Boiling Point: 213.2±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 82.8±27.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Pyrrolo[1,2-a]pyrazin-1-one is a heterocyclic compound that has attracted attention in the field of medicinal chemistry due to its unique structural characteristics and potential biological activities. This compound features a fused bicyclic system composed of a pyrrole ring and a pyrazine ring, contributing to its intriguing electronic and steric properties. The molecular formula for pyrrolo[1,2-a]pyrazin-1-one is C7H6N2O, and it is recognized for the presence of a carbonyl group that enhances its reactivity.

The discovery of pyrrolo[1,2-a]pyrazin-1-one can be traced back to the exploration of bicyclic heterocycles as potential pharmacophores. Researchers were investigating compounds with fused ring systems that could exhibit improved interactions with biological targets compared to their monocyclic counterparts. The combination of the pyrrole and pyrazine rings offers a diverse array of functionalization possibilities, making this compound a valuable scaffold for drug development.

One of the most notable applications of pyrrolo[1,2-a]pyrazin-1-one is its role as a building block in the synthesis of novel pharmaceuticals. The compound's carbonyl group can be readily modified to introduce various substituents, enabling the design of derivatives with enhanced biological activity. This property has made pyrrolo[1,2-a]pyrazin-1-one an important intermediate in the development of therapeutic agents targeting a range of conditions, including cancer, bacterial infections, and neurological disorders.

Pyrrolo[1,2-a]pyrazin-1-one has also been studied for its potential as a lead compound in drug discovery. Its structural features allow for the exploration of structure-activity relationships (SAR), which is crucial for optimizing the efficacy and selectivity of new drugs. Preliminary studies have suggested that derivatives of pyrrolo[1,2-a]pyrazin-1-one exhibit promising anticancer and antimicrobial properties, making it a compound of interest for further investigation.

In addition to its medicinal applications, pyrrolo[1,2-a]pyrazin-1-one is being explored in materials science. The compound's ability to form conjugated systems can lead to interesting optical and electronic properties, which are advantageous for the development of organic semiconductors and photovoltaic materials. Researchers are investigating the potential of pyrrolo[1,2-a]pyrazin-1-one and its derivatives in organic electronics, aiming to harness their unique properties for practical applications.

In summary, pyrrolo[1,2-a]pyrazin-1-one is a significant compound in the realms of medicinal chemistry and materials science. Its unique bicyclic structure, combined with its potential biological activities, makes it an attractive candidate for further research and development. As scientists continue to explore its applications, pyrrolo[1,2-a]pyrazin-1-one is poised to contribute to advancements in drug discovery and the development of innovative materials.

References

2023. Synthesis, antimicrobial and antioxidant activity of novel 1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acids, esters, and amides thereof. Monatshefte für Chemie - Chemical Monthly, 154(9).
DOI: 10.1007/s00706-023-03118-8

2011. 1-(Trifluoromethyl)-3,4-dihydropyrrolo-[1,2-a] pyrazines: synthesis and reactions with O- and N-nucleophiles. Chemistry of Heterocyclic Compounds, 47(1).
DOI: 10.1007/s10593-011-0663-x

2010. Identification and SAR of novel pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1). Bioorganic & Medicinal Chemistry Letters, 20(3).
DOI: 10.1016/j.bmcl.2009.12.026