85209-84-3

Upstream product

• 144927-66-2 (2R,3R,4S,5R)-2-(4-Chloro-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-5-methyl-tetrahydro-furan-3,4-diol 
• 123148-78-7 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 291535-34-7 5-deoxy-2,3-O-isopropylidene-α-D-ribofuranosyl chloride 
• 186394-15-0 4-chloro-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1323111-51-8 4-chloro-5-iodo-7-(2,3-di-O-acetyl-5-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Efficient and practical synthesis of 5′-deoxytubercidin and its analogues via Vorbrggen glycosylation

An efficient and practical synthesis of naturally occurring marine nucleosides 5′-deoxytubercidins on a 10 gram scale in good overall yield is reported. The key step was the Vorbrggen glycosylation of pyrrolo[2,3-d]pyrimidines with 5-deoxy-1,2,3-tri-O-ace

Adenosine kinase inhibitors. 1. Synthesis, enzyme inhibition, and antiseizure activity of 5-iodotubercidin analogues

Adenosine receptor agonists produce a wide variety of therapeutically useful pharmacologies. However, to date they have failed to undergo successful clinical development due to dose-limiting side effects. Adenosine kinase inhibitors (AKIs) represent an alternative strategy, since AKIs may raise local adenosine levels in a more site- and event-specific manner and thereby elicit the desired pharmacology with a greater therapeutic window. Starting with 5-iodotubercidin (IC50 = 0.026 μM) and 5'-amino-5'- deoxyadenosine (IC50 = 0.17 μM) as lead inhibitors of the isolated human AK, a variety of pyrrolo[2,3-d]pyrimidine nucleoside analogues were designed and prepared by coupling 5-substituted-4-chloropyrrolo[2,3-d]pyrimidine bases with ribose analogues using the sodium salt-mediated glycosylation procedure. 5'-Amino-5'-deoxy analogues of 5-bromo- and 5-iodotubercidins were found to be the most potent AKIs reported to date (IC50s 0.001 μM). Several potent AKIs were shown to exhibit anticonvulsant activity in the rat maximal electric shock (MES) induced seizure assay.

4-Amino-7-(5-deoxy-beta-D-ribofuranosyl)-5-iodo-7H-pyrrolo[2,3-d] pyrimidine

A compound, 4-Amino-7-(5-deoxy-beta-D-ribofuranosyl)-5-iodo-7H-pyrrolo[2,3-d] pyrimidine, as well as process to produce this compound, are disclosed. The compound is useful as a muscle relaxant.