6741-71-5

Basic information

• Product Name: 1-(4'-thio-beta-ribofuranosyl)thymine
• Synonyms: 1-(4'-thio-beta-ribofuranosyl)thymine;1-(4-thio-beta-D-ribofuranosyl)-5-Methyluracil;5-Methyl-4'-thiouridine
• CAS NO: 6741-71-5
• Molecular Formula: C10H14N2O5S
• Molecular Weight: 274.29356
• Mol File: 6741-71-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.592±0.06 g/cm3(Predicted)
• PKA: 9.55±0.10(Predicted)
• CAS DataBase Reference: 1-(4'-thio-beta-ribofuranosyl)thymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4'-thio-beta-ribofuranosyl)thymine(6741-71-5)
• EPA Substance Registry System: 1-(4'-thio-beta-ribofuranosyl)thymine(6741-71-5)

Safety Data

• Hazardous Substances Data: 6741-71-5(Hazardous Substances Data)

Usage

Explanation

Also known as 4-thiothymine, it is a modified form of the nucleoside thymine, a component of DNA.

Explanation

The thioether group replaces the oxygen in the ribose ring, resulting in a unique structure.

Explanation

The compound has shown antiviral activity against several viruses and has the ability to disrupt viral replication and inhibit cancer cell growth.

Explanation

Studies have demonstrated the compound's effectiveness in inhibiting the replication of these viruses.

Explanation

The compound's unique structure allows it to interfere with the processes of viral replication and cancer cell proliferation.

Explanation

To fully understand the compound's mechanisms of action and potential medical applications, additional studies and trials are necessary.

Chemical modification

Contains a thioether group

Potential applications

Antiviral and anticancer drugs

Antiviral activity

Potent against HIV and herpes simplex virus

Mechanism of action

Disruption of viral replication and inhibition of cancer cell growth

Current status

Further research and clinical trials needed

Upstream product

• 65-71-4 thymin 
• 161512-40-9 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-D-ribofuranose 
• 89824-86-2 (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran 
• 358359-77-0 1-(2,3,5-tri-O-benzyl-4-thio-α, β-L-xylofuranosyl) thymine 
• 197716-38-4 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 
• 208755-45-7 1-(2,3,5-tri-O-benzyl-4-thio-L-arabino-furanosyl)thimine 
• 208755-44-6 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-L-arabinofuranose 
• 208755-43-5 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-L-arabinitol 
• 100896-16-0 2,3,5-tri-O-benzyl-D-xylitol 
• 100806-53-9 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-D-xylitol 
• 1824-96-0 methyl xylofuranoside 
• 87-72-9 D-Xylose 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 187590-79-0 (2R,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-tetrahydro-thiophene 1-oxide 

Relevant articles and documents

4'-thio-L-xylofuranosyl nucleosides, precursors thereof, preparation and use thereof

Compounds represented by the formula 1: A is selected from the group consisting of wherein each R individually is H or acyl, Y is X, N3, NH2, monoalkylamino, or dialkylamino; Z is O or S; and X is selected from the group consisting o

Synthesis and biological activity of 4′-thio-L-xylofuranosyl nucleosides

A series of 4′-thio-L-xylofuranosyl nucleosides were prepared and evaluated as potential anticancer and antiviral agents. The details of a convenient and high-yielding synthesis of the carbohydrate precursor 1-O-acetyl-2,3,5-tri-O-benzyl-4- thio-L-xylofuranose (6) are presented. Proof of structure and configuration at all chiral centers of the nucleosides was obtained by proton and carbon NMR. All target compounds were evaluated in a series of human cancer cell lines in culture and as antiviral agents.

Synthesis of L-enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides

L-Enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides were synthesized from D-xylose. Methyl 2,3,5-tri-O-benzyl-D-xylofuranoside 6 was converted to the corresponding xylitol 7, which was treated with MsCl and then Na2S to give 1,4-anhydro-L-4-thioarabitol 8. As previously reported, Pummerer rearrangement of 8 followed by glycosylation with a silylated thymine and N4-acetylcytosine derivative and deprotection gave the corresponding α- and β-L-4'-thioarabinofuranosyl pyrimidine nucleosides.