Document Detail


Synthesis and biological evaluation of 2,8-disubstituted 9-benzyladenines: discovery of 8-mercaptoadenines as potent interferon-inducers.
MedLine Citation:
PMID:  12788345     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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 microM.
Authors:
Kosaku Hirota; Kazunori Kazaoka; Hironao Sajiki
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  11     ISSN:  0968-0896     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2003 Jul 
Date Detail:
Created Date:  2003-06-05     Completed Date:  2004-04-06     Revised Date:  2007-11-15    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  2715-22     Citation Subset:  IM    
Affiliation:
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu 502-8585, Japan. hirota@gifu-pu.ac.jp
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MeSH Terms
Descriptor/Qualifier:
Adenine / analogs & derivatives*,  chemical synthesis,  pharmacology*
Animals
Antiviral Agents / chemical synthesis*,  pharmacology
Cells, Cultured
Drug Design
Gene Expression Regulation / drug effects
Hepatitis C / drug therapy
Immunotherapy / methods
Interferons / agonists*,  biosynthesis
Mice
Spleen / cytology,  secretion
Vesicular stomatitis Indiana virus / drug effects
Chemical
Reg. No./Substance:
0/Antiviral Agents; 4261-14-7/9-benzyladenine; 73-24-5/Adenine; 7390-62-7/meradine; 9008-11-1/Interferons

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