5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluoro-N-(2-methyl-1-oxopropyl)guanosine
[CAS# 144089-96-3]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleotides and their analogues
• Name: 5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluoro-N-(2-methyl-1-oxopropyl)guanosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-fluoro-4-hydroxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• Molecular Formula: C₃₅H₃₆FN₅O₇
• Molecular Weight: 657.69
• CAS Registry Number: 144089-96-3
• SMILES: CC(C)C(=O)NC1=NC2=C(C(=O)N1)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)O)F

Properties

• Solubility: Insoluble (9.2E^-5 g/L) (25 ºC), Calc.^*
• Density: 1.38±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*

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

Safety Data

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

Discovory and Applicatios

5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluoro-N-(2-methyl-1-oxopropyl)guanosine is a synthetically modified nucleoside designed to enhance stability, cellular uptake, and biological activity. This complex chemical structure combines protecting groups and substituents, making it a promising drug candidate for a variety of therapeutic and research applications.

The synthesis of 5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluoro-N-(2-methyl-1-oxopropyl)guanosine is part of an ongoing effort to develop nucleoside analogs with improved pharmacokinetic properties. Addition of protecting groups such as the DMT group and modifications such as 2'-fluoro substitutions are intended to enhance nucleoside stability and functionality.

This nucleoside analog has several key modifications: the DMT (bis(4-methoxyphenyl)benzyl) group protects the 5' hydroxyl group, facilitating oligonucleotide synthesis; the 2'-deoxy-2'-fluoro substitution enhances resistance to enzymatic degradation and improves stability in biological environments; and the N-(2-methyl-1-oxopropyl) group increases lipophilicity and enhances cellular uptake.

The protecting groups and substitutions on 5'-O-[bis(4-methoxyphenyl)benzyl]-2'-deoxy-2'-fluoro-N-(2-methyl-1-oxopropyl)guanosine prevent degradation and enable selective reactions in biochemical processes. The DMT group ensures selective deprotection in oligonucleotide synthesis, while the 2'-fluoro substitution provides stability by resisting nuclease activity. The N-(2-methyl-1-oxopropyl) group enhances lipophilicity, promoting efficient cellular uptake and incorporation into DNA or RNA.

This nucleoside analog has been studied for its potential in antiviral therapy. Its stability and ability to integrate into viral DNA make it a promising candidate for inhibiting viral replication, potentially treating infections such as HIV and hepatitis.

5'-O-[bis(4-methoxyphenyl)benzyl]-2'-deoxy-2'-fluoro-N-(2-methyl-1-oxopropyl)guanosine has been studied for its anticancer properties. By integrating into the DNA of rapidly dividing cancer cells, it can disrupt replication and induce apoptosis, making it a potential chemotherapeutic agent.

This compound plays a vital role in the synthesis of oligonucleotides for research and therapeutic applications. Its protecting groups ensure accurate and efficient assembly of DNA and RNA sequences, facilitating advances in genetic research and therapy.

In research, this modified nucleoside is used to study nucleic acid interactions and the effects of nucleoside modifications on DNA and RNA stability and function. Its enhanced stability allows researchers to study these processes more efficiently.

Fluorine substitution and protecting groups significantly increase resistance to enzymatic degradation. The N-(2-methyl-1-oxopropyl) group enhances cellular uptake and stability. This modified nucleoside has applications in antiviral, anticancer, and molecular biology research. However, the synthesis of this modified nucleoside can be complex and costly; further research is needed to optimize its therapeutic efficacy and minimize potential side effects.