N4-Acetyl-2'-deoxy-2'-fluorocytidine
[CAS# 159414-97-8]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: N4-Acetyl-2'-deoxy-2'-fluorocytidine
• Synonyms: N-[1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• Protein Sequence: N
• Molecular Formula: C₁₁H₁₄FN₃O₅
• Molecular Weight: 287.24
• CAS Registry Number: 159414-97-8
• SMILES: CC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)F

Safety Data

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

Discovory and Applicatios

N4-acetyl-2'-deoxy-2'-fluorocytidine is a modified nucleoside that has received much attention for its potential in medicinal chemistry and molecular biology. This compound, called acetyl-DF-cytidine, combines structural and chemical modifications to enhance its functionality and stability.

Acetyl-DF-cytidine was developed as part of a research effort to create nucleoside analogs with improved properties. The compound is synthesized by selective acetylation of the N4 position of cytidine followed by the introduction of a fluorine atom at the 2' position of the sugar moiety. The synthesis involves protecting groups and specific reaction conditions to ensure high purity and yield of the final product.

The unique modification of acetyl-DF-cytidine lends it potential as an antiviral and anticancer agent. The fluorine substitution at the 2' position of the deoxyribose enhances the stability and bioavailability of the compound, which is essential for the development of effective drugs. This stability makes it a promising candidate for further investigation of its efficacy against viral infections and tumors.

In molecular biology, acetyl-DF-cytidine is a useful tool for studying nucleic acid interactions and modifications. Its structural alterations compared to native cytidine allow researchers to explore the effects of such modifications on nucleic acid behavior, including binding affinity and structural changes.

The acetyl and fluorine groups in acetyl-DF-cytidine improve its pharmacokinetic properties, making it a valuable compound in drug development. Its enhanced stability and reduced susceptibility to enzymatic degradation suggest that it could be developed into a more effective and durable drug formulation.