N4-Benzoylcytosine
[CAS# 26661-13-2]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleotides and their analogues
• Name: N4-Benzoylcytosine
• Synonyms: N-(2-Oxo-1,2-dihydro-4-pyrimidinyl)benzamide; N-(2-Oxo-3H-pyrimidin-4-yl)benzamide
• Molecular Formula: C₁₁H₉N₃O₂
• Molecular Weight: 215.21
• CAS Registry Number: 26661-13-2
• EC Number: 628-907-2
• SMILES: C1=CC=C(C=C1)C(=O)NC2=CC=NC(=O)N2

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: >300 °C (dec.)
• Index of Refraction: 1.652, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-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.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

N4-Benzoylcytosine is a synthetic derivative of cytosine, a key nucleobase that plays a vital role in the structure of nucleic acids such as DNA and RNA. The discovery of N4-benzoylcytosine can be traced back to the mid-20th century when researchers began to explore modifications of nucleobases to enhance their properties for various applications, particularly in the field of molecular biology and medicinal chemistry. The introduction of a benzoyl group at the N4 position of cytosine alters its chemical properties, making it a valuable compound for study.

The synthesis of N4-benzoylcytosine typically involves the acylation of cytosine using benzoyl chloride or benzoyl anhydride in the presence of a suitable base. This modification provides a handle for further chemical transformations and allows researchers to explore its potential biological activities. The resulting compound retains the essential properties of cytosine while offering new avenues for research and application.

N4-benzoylcytosine has garnered attention for its potential role in nucleic acid chemistry and biochemistry. Its structure makes it a useful building block for the synthesis of nucleoside analogs, which can be employed in the development of antiviral and anticancer agents. By incorporating N4-benzoylcytosine into oligonucleotides, researchers can study its interaction with complementary DNA or RNA sequences, providing insights into the mechanisms of nucleic acid recognition and hybridization.

In addition to its applications in nucleic acid research, N4-benzoylcytosine has been investigated for its potential as a pharmaceutical agent. Its structural modifications may enhance the stability and selectivity of nucleoside analogs, contributing to the development of targeted therapies. Researchers are particularly interested in exploring the compound's efficacy against viral infections and various types of cancer, where the manipulation of nucleic acid metabolism can lead to therapeutic benefits.

Furthermore, N4-benzoylcytosine serves as a valuable tool in chemical biology for studying enzyme-substrate interactions. It can act as a substrate for specific enzymes, allowing scientists to investigate the mechanisms of enzyme catalysis and the influence of structural modifications on enzymatic activity. Such studies contribute to a deeper understanding of fundamental biochemical processes and the development of enzyme inhibitors.

The exploration of N4-benzoylcytosine is ongoing, with researchers continuously investigating its chemical properties and biological activities. Advances in synthetic methodologies and analytical techniques facilitate the discovery of novel derivatives and their applications in various fields, including drug discovery and molecular diagnostics.

In summary, N4-benzoylcytosine is a significant synthetic derivative of cytosine with a variety of applications in nucleic acid chemistry, medicinal chemistry, and chemical biology. Its discovery and ongoing study highlight the importance of nucleobase modifications in developing new therapeutic agents and understanding fundamental biological processes.

References

1979. Glycosylation of N4-benzoylcytosine with acetylated glycals. Chemistry of Heterocyclic Compounds.
DOI: 10.1007/bf00471928

2022. N-Glycosides. Synthesis and Characterization of Glycosides.
DOI: 10.1007/978-3-030-97854-9_3

2006. Synthesis of Glycol Nucleic Acids. .
DOI: 10.5055/s-2006-926313