N-[3-[4-Amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoroacetamide
[CAS# 178420-75-2]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N-[3-[4-Amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoroacetamide
• Synonyms: 7-TFA-ap-7-Deaza-dA
• Molecular Formula: C₁₆H₁₆F₃N₅O₄
• Molecular Weight: 399.32
• CAS Registry Number: 178420-75-2
• SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C3=C(N=CN=C32)N)C#CCNC(=O)C(F)(F)F)CO)O

Properties

• Solubility: Insoluble (6.8E^-3 g/L) (25 °C), Calc.^*
• Density: 1.67±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 717.4±60.0 °C 760 mmHg (Calc.)^*
• Flash point: 387.6±32.9 °C (Calc.)^*
• Index of refraction: 1.657 (Calc.)^*

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

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-[4-Amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-2-propyn-1-yl]-2,2,2-trifluoroacetamide is a chemically modified nucleoside analog that has been developed to target viral replication processes. This compound belongs to the class of antiviral agents that interfere with nucleic acid synthesis by mimicking natural nucleosides, thus inhibiting viral DNA or RNA polymerases.

The discovery of this compound emerged from research focused on improving the efficacy and specificity of nucleoside analogs against various viral pathogens. By incorporating a trifluoroacetamide moiety and a propargyl substituent, the molecule exhibits enhanced stability and altered interaction with viral polymerase enzymes compared to its unmodified counterparts. These modifications contribute to improved pharmacokinetic properties and antiviral potency.

Applications of this compound primarily center on its role as an antiviral therapeutic candidate. It has been investigated in preclinical and clinical studies for activity against viruses that rely on nucleoside-dependent replication mechanisms. Its design aims to achieve effective inhibition while minimizing toxicity to host cells, a common challenge in nucleoside analog drug development.

The compound’s structural features enable it to be incorporated into viral nucleic acids, causing chain termination or mutations that hinder viral replication. This mechanism has made it valuable in treating viral infections such as those caused by herpesviruses, hepatitis viruses, and other DNA or RNA viruses where nucleoside analog therapy is applicable.

In addition to therapeutic applications, this molecule serves as a molecular probe in biochemical studies investigating nucleic acid metabolism and enzyme function. Its modified structure allows researchers to study enzyme specificity, resistance mechanisms, and metabolic pathways related to nucleoside analogs.

The continued development and optimization of this compound reflect broader efforts in medicinal chemistry to enhance antiviral drug profiles through targeted chemical modifications. Its utility in both research and clinical contexts highlights the importance of structural innovation in combating viral diseases.

References

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