63423-94-9

Usage

Uses

Used in Pharmaceutical Industry:
1-(2,3,5-Tri-O-acetyl--D-ribofuranosyl)-4,6-dichloroimidazo[4,5-c]pyridine is used as a key intermediate in the synthesis of 3-Deazaadenosine (D200875), a nucleoside analog with potential therapeutic applications. It plays a crucial role in the development of new drugs for the treatment of various diseases, including cancer and viral infections.

Upstream product

• 2589-12-0 4,6-dichloro-1H-imidazo<4,5-c>pyridine 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 2897-43-0 2,6-dichloro-3-nitropyridin-4-amine 
• 101079-63-4 3,4-diamino-2,6-dichloropyridine 
• 39727-26-9 β-D-Ribofuranose-1,2,3,5-tetraacetate 

Downstream Products

• 40656-71-1 2,6-dichloro-9-(β-D-ribofuranosyl)-3-deazapurine 

Relevant academic research and scientific papers

MODULATORS OF 5'-NUCLEOTIDASE, ECTO AND THE USE THEREOF

Compounds that modulate the conversion of AMP to adenosine by 5'- nucleotidase, ecto, and compositions containing the compounds and methods for synthesizing the compounds, are described herein. The use of such compounds and compositions for the treatment and/or prevention of a diverse array of diseases, disorders and conditions, including cancer- and immune-related disorders, that are mediated by 5'-nucleotidase, ecto is also provided.

A convenient route for the synthesis of 3-deazaspongosine

The first chemical synthesis of the 3-deazaspongosine nucleoside is described, starting from commercially available 4-amino-2,6-dichloropyridine. The key step is the introduction of required functional groups at the 2 and 6 positions of the 4-amino-3-nitropyridine without any conflict in the synthesis of nucleobase. Regioselective nucleophilic substitution with allyl alkoxide at the 2 position of 4-amino-2,6-dimethoxypyridine, followed by sequential deallylation and chlorination led to the desired 2-chloro derivative. Ring closure of the 3,4-diaminopyridine and stereoselective glycosylation of the imidazo[4,5-c]pyridine with tetraacetate-protected ribofuranose gave only the N9-β-isomer. A final nucleophilic displacement of the 6-chloride by hydrazine followed by reduction with Raney Nickel gave the desired 3-deazaspongosine. The synthesis of 3-deazaspongosine by the stereoselective glycosylation of imidazo[4,5-c]pyridine with tetraacetate-protected ribofuranose is described. The key step is the synthesis of the nucleobase starting from 2,6-dimethoxy-3-nitropyridin-4-amine by introducing the required functional groups at the 2 and 6 positions through the regioselective addition of allyl alcohol. Copyright

Deaza- and deoxyadenosine derivatives: Synthesis and inhibition of animal viruses as human infection models

N6-Cycloalkyl-2′,3′-dideoxyadenosine derivatives and (2-chloro)-N6-cycloheptyl-3-deazaadenosine have been synthesized and tested, along with other (deaza)purine (deoxy)nucleosides from our chemical library, as inhibitors of virus replication against Bovine Herpes Virus 1 (BHV-1) and sheep Maedi/Visna Virus (MVV). Most compounds demonstrated good antireplicative activity against MVV, showing also low cell toxicity.