3-Bromo-3-deazaneplanocin and 3-bromo-3-deazaaristeromycin: synthesis and antiviral activity.
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.
Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, USA.
Chong
C
Liu
Qi
Q
Chen
Stewart W
SW
Schneller
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D002522:Chlorocebus aethiops; D018360:Crystallography, X-Ray; D006367:HeLa Cells; D006801:Humans; D008968:Molecular Conformation; D014709:Vero Cells; D014779:Virus Replication / Q000187:drug effects; D014780:Viruses / Q000187:drug effects
C576469:3-bromo-3-deazaaristeromycin; C576468:3-bromo-3-deazaneplanocin; D000998:Antiviral Agents; C048460:3-deazaneplanocin; C034583:3-deazaaristeromycin; D000241:Adenosine