226907-93-3

Upstream product

• 5451-40-1 2,6 dichloropurine 
• 60598-48-3 5-amino-1-benzyl-1H-imidazole-4-carbonitrile 
• 56046-25-4 6-amino-9-benzyl-2-chloropurine 
• 109-73-9 N-butylamine 
• 123-72-8 butyraldehyde 
• 7674-36-4 9-Benzylpurine-2,6-diamine 

Downstream Products

• 226908-08-3 6-Amino-9-benzyl-8-bromo-2-butylaminopurine 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 2,8-disubstituted 9-benzyladenines: Discovery of 8-mercaptoadenines as potent interferon-inducers

Recently, we have identified 9-benzyl-8-hydroxyadenines bearing an appropriate substituent (a butoxy, propylthio or butylamino group) at the 2-position as potent interferon (IFN)-inducers. Herein we report the design, synthesis, and IFN-inducing activity of 8-substituted 9-benzyladenines possessing such an appropriate substituent at the 2-position. Introduction of the appropriate substituent into the 2-position of the adenine nucleus gave rise to expression of the activity even in 9-benzyladenines bearing no hydroxyl group at the 8-position. An amino group at the 6-position and a hydroxyl or thiol group carrying an acidic proton at the 8-position are required to express excellent IFN-inducing activity. 9-Benzyl-2-butoxy-8-mercaptoadenine (9) indicated the most potent activity with MEC of 0.001 μM.

Synthesis and structure-activity relationships of 2-amino-8- hydroxyadenines as orally active interferon inducing agents

Recently, we have reported the 8-hydroxyadenine derivatives (2-4) as a novel class of interferon (IFN) inducing agents. In the present study, a series of 8-hydroxyadenines, which possess various amino moieties at the adenine C(2)-position, were synthesized and evaluated for their ability to induce endogenous IFN in comparison to the known active agent, Imiquimod. Among the compounds prepared, compound 9o possessing a 2-methoxyethylamino group at C(2)-position of adenine was found to exhibit potent IFN inducing activity in vivo. Compound 9o induced IFN from the dosage of 0.1 mg/kg, which was 30-fold potent than that of Imiquimod, and showed a good oral bioavailability (F=81%).