N-[3-[2-Amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoroacetamide
[CAS# 666847-77-4]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N-[3-[2-Amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoroacetamide
• Synonyms: 7-TFA-ap-7-Deaza-dG
• Molecular Formula: C₁₆H₁₆F₃N₅O₅
• Molecular Weight: 415.32
• CAS Registry Number: 666847-77-4
• SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C3=C2N=C(NC3=O)N)C#CCNC(=O)C(F)(F)F)CO)O

Properties

• Solubility: Practically insoluble (0.096 g/L) (25 °C), Calc.^*
• Density: 1.76±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2018 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

N-[3-[2-Amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoroacetamide is a synthetic nucleoside analogue structurally related to naturally occurring nucleosides that play essential roles in nucleic acid metabolism. This compound features a modified pyrrolo[2,3-d]pyrimidine base linked to a 2-deoxy-β-D-erythro-pentofuranose sugar, coupled with a trifluoroacetamide group attached through a propargyl linker. Its design aims to combine nucleoside mimicry with chemical modifications to enhance biological activity or pharmacokinetic properties.

The discovery of this class of compounds stems from ongoing efforts in medicinal chemistry to develop nucleoside analogues capable of interacting with nucleic acid-processing enzymes such as polymerases, kinases, and nucleoside transporters. These analogues are often synthesized to interfere with viral replication, cancer cell proliferation, or other pathological processes involving DNA and RNA synthesis.

The structural features of this molecule, particularly the trifluoroacetamide moiety and the propargyl linker, confer increased stability and cell permeability relative to unmodified nucleosides. Additionally, the presence of the 2-deoxy sugar and the modified heterocyclic base enables it to function as a substrate mimic for enzymes that recognize natural nucleosides, thereby potentially inhibiting their activity or being incorporated into nucleic acids with altered properties.

Applications of such nucleoside analogues primarily focus on antiviral and anticancer research. By mimicking the natural substrates of nucleic acid enzymes, these compounds can act as chain terminators or enzyme inhibitors, disrupting nucleic acid synthesis in target cells or viruses. This mode of action makes them valuable candidates in the development of therapeutics against diseases like HIV, hepatitis, and certain types of cancer.

In biochemical studies, these analogues also serve as tools to investigate the mechanisms of nucleic acid metabolism, enzyme specificity, and resistance pathways. Their chemical modifications allow researchers to probe interactions at the molecular level and to design next-generation compounds with improved efficacy and reduced toxicity.

Overall, N-[3-[2-Amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoroacetamide represents a sophisticated nucleoside analogue engineered for biological and medicinal chemistry applications. Its structural components reflect strategic modifications aimed at enhancing pharmacological potential and serving as a probe in nucleic acid-related research.

References

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