| Synthesis and biological evaluation of 2,8-disubstituted 9-benzyladenines: discovery of 8-mercaptoadenines as potent interferon-inducers. | |
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MedLine Citation:
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PMID: 12788345 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Kosaku Hirota; Kazunori Kazaoka; Hironao Sajiki |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Bioorganic & medicinal chemistry Volume: 11 ISSN: 0968-0896 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2003 Jul |
Date Detail:
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Created Date: 2003-06-05 Completed Date: 2004-04-06 Revised Date: 2007-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: England |
Other Details:
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Languages: eng Pagination: 2715-22 Citation Subset: IM |
Affiliation:
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Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu 502-8585, Japan. hirota@gifu-pu.ac.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Adenine
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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:
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0/Antiviral Agents; 4261-14-7/9-benzyladenine; 73-24-5/Adenine; 7390-62-7/meradine; 9008-11-1/Interferons |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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