140623-93-4

Basic information

• Product Name: 1,4-ANHYDRO-2-DEOXY-2-(THYMIN-1-YL)-D-ARABINITOL
• Synonyms: 1,4-ANHYDRO-2-DEOXY-2-(THYMIN-1-YL)-D-ARABINITOL
• CAS NO: 140623-93-4
• Molecular Formula: C₁₀H₁₄N₂O₅
• Molecular Weight: 242.23
• Mol File: 140623-93-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,4-ANHYDRO-2-DEOXY-2-(THYMIN-1-YL)-D-ARABINITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-ANHYDRO-2-DEOXY-2-(THYMIN-1-YL)-D-ARABINITOL(140623-93-4)
• EPA Substance Registry System: 1,4-ANHYDRO-2-DEOXY-2-(THYMIN-1-YL)-D-ARABINITOL(140623-93-4)

Safety Data

• Hazardous Substances Data: 140623-93-4(Hazardous Substances Data)

Usage

Synthetic molecule

It is a man-made compound, not found naturally in living organisms.

Derivative of D-arabinitol

It is derived from the sugar D-arabinitol, which is a pentitol (five-carbon sugar alcohol).

Contains a thymine base

The molecule has a thymine base attached to it, which is one of the four nucleobases in DNA.

Nucleoside analog

It is structurally similar to a natural nucleoside but with some modifications, making it an analog.

Antiviral and antitumor potential

It has been studied for its potential use in treating viral infections and cancer.

Inhibition of DNA and RNA synthesis

The molecule is designed to interfere with the replication of viral and tumor cells by inhibiting their DNA and RNA synthesis.

Activity against herpes simplex virus

Research has shown that it exhibits promising antiviral activity against herpes simplex virus (HSV).

Activity against cytomegalovirus

It also shows potential in inhibiting the replication of cytomegalovirus (CMV).

Antitumor activity

The molecule has demonstrated antitumor activity against various cancer cell lines.

Unique structure

Its distinct chemical structure contributes to its potential therapeutic applications.

Further study and drug development

Due to its promising properties, it is an interesting candidate for further research in the development of new antiviral and antitumor drugs.

Upstream product

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• 160308-07-6 1,4-anhydro-2-azido-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-arabinitol 
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• 132151-65-6 (E)-3-methoxy-2-methylacryloyl isocyanate 
• 1824-96-0 methyl ribofuranoside 
• 259137-59-2 2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)-4(R)-aminotetrahydrofuran 
• 259137-71-8 2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)-4(R)-azidotetrahydrofuran 

Downstream Products

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• 160308-10-1 1,4-anhydro-5-O-benzoyl-2-deoxy-2-<3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl>-D-lyxitol 
• 201932-40-3 Diisopropyl-phosphoramidous acid (2R,3S,4R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 259137-68-3 Benzoic acid (2R,3S,4R)-3-methanesulfonyloxy-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 215032-04-5 1-{(3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-3-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 143191-83-7 1-[(3S,5S)-5-(hydroxymethyl)tetrahydrofuran-3-yl]thymine 

Relevant articles and documents

A new general synthesis of isomeric nucleosides

An efficient new method for the synthesis of isonucleosides is described. The key step in the synthesis was the direct coupling of purine and pyrimidine bases with the cyclic sulfate of a carbohydrate intermediate. This reaction proceeded with high regiospecificity and stereospecificity.

Synthesis and antiviral studies of unsaturated analogues of isomeric dideoxynucleosides

Novel isomeric dideoxynucleosides with unsaturation in the carbohydrate moiety have been synthesized. For example, isod4A was synthesized through a rearrangement reaction involving a cyclonucleoside. Support for the structures of both purine and pyrimidin

Synthesis of isonucleosides related to AZT and AZU

Approaches to 1,4-anhydro-3-azido-2,3-dideoxy-2-[3,4-dihydro-2,4-dioxo-5- methyl-1(2H)-pyrimidinyl]-D-arabinitol, and the related uracil derivative, have been developed. These conceptually new, optically active analogs of AZT, derived from 1,4-anhydro-D-ribitol, are among the first examples of regioisomeric analogs of AZT.

SYNTHETIC APPROACHES TO NEW REGIOISOMERS OF AZT AND AZU

Approaches to 1,4-anhydro-3-α-azido-2,3-dideoxy-2-β--D-arabinitol and 1,4-anhydro-3-α-azido-2,3-dideoxy-2-β--D-arabinitol, conceptually new hydrolytically stable, optically active analogs of 3'-α-azido-3'-deoxythymidine (AZT) have been developed.These are among the first examples of regioisomeric analogs of AZT.The key synthetic steps and key intermediates are described.The generality aspects of the approaches are addressed.