Article

3-Bromo-3-deazaneplanocin and 3-bromo-3-deazaaristeromycin: synthesis and antiviral activity.

Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, USA.
Bioorganic & medicinal chemistry letters (impact factor: 2.65). 07/2012; 22(16):5182-4. DOI:10.1016/j.bmcl.2012.06.075
Source: PubMed

ABSTRACT As an outgrowth of our program to explore 3-deazaadenine carbocyclic nucleosides, 3-bromo-3-deazaneplanocin (5) and 3-bromo-3-deazaaristeromycin (6) have been synthesized from a readily available cyclopentenol and cyclopentanone and either 4-amino- or 4-chloro-1H-imidazo[4,5-c]pyridine (6-amino- or 6-chloro-3-deazaadenine) in 5 steps and 7 steps, respectively. Antiviral analysis found 5 to display significant activity towards a number of (-)-ssRNA and a few dsDNA viruses. Compound 6 was less active than 5 against selected examples of those viruses affected by 5.

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Keywords

3-bromo-3-deazaaristeromycin
 
3-deazaadenine carbocyclic nucleosides
 
6-chloro-3-deazaadenine
 
active
 
Antiviral analysis
 
available cyclopentenol
 
Compound 6
 
cyclopentanone
 
outgrowth
 

Chong Liu