Synthesis of 6-Substituted 9-Benzyl-8-hydroxypurines with Potential Interferon-Inducing Activity

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概要

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• Various 6-substituted 9-benzyl-8-hydroxypurines were synthesized in order to investigate the structure-activity relationship at the 6-position of 9-benzyl-8-hydroxyadenine (1), which is a lead compound for the screening of interferon (IFN)-inducing activity. 6-Unsubstituted, mercapto-, methylthio- and hydroxy-9-benzyl-8-hydroxy-purines (2-5) were prepared from 5-amino-1-benzyl-4-cyano-2-hydroxyimidazole (9). Synthesis of a 6-methoxy analog (6) was conducted from 5-amino-4-benzylamino-6-chloropyrimidine (13). 6-Alkylamino and acylamino-purines (7 and 8) were also prepared by alkylation and acylation of 1, respectively. Since these compounds (2-8) indicated no activity, it was found that a free amino group of 1 is required for the expression of IFN-inducing activity.

• 公益社団法人日本薬学会の論文
• 2003-05-01

著者

• Hirota Kosaku

  Laboratory Of Medicinal Chemistry Gifu Pharmaceutical University

• Hirota Kosaku

  Laboratory Of Medicinal Chemisutry Gifu Pharmaceutical University

• SAJIKI Hironao

  Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University

• Sajiki Hironao

  Laboratory Of Medicinal Chemisutry Gifu Pharmaceutical University

• Sajiki Hironao

  Laboratories Of Medicinal Chemistry Gifu Pharmaceutical University

• KAZAOKA Kazunori

  Laboratory of Medicinal Chemisutry, Gifu Pharmaceutical University

• Kazaoka Kazunori

  Laboratory Of Medicinal Chemisutry Gifu Pharmaceutical University

• Sajiki Hironao

  Laboratories Of Medicinal Chemistry Gifu Pharmaceutical Univ.

関連論文

• Reactivities of 6-Amino-1,3-dimethyl-5-thioformyluracil toward Nucleophiles and Its Application to Synthesis of Pyrido[2,3-d]pyrimidines
• Pd/C(en) Catalyzed Chemoselective Hydrogenation in the Presence of Aryl Nitriles
• Efficient and Selective Pt/C-Catalyzed H-D Exchange Reaction of Aromatic Rings
• Synthesis of 6-Substituted 9-Benzyl-8-hydroxypurines with Potential Interferon-Inducing Activity
• Novel and Efficient Synthesis of 8-Oxoadenine Derivatives.
• Diversity of Rearrangement of 3-Substituted 5-Carbamoyl-1-phenyluracil Derivatives.
• Synthesis of Pyrimidine Derivatives Possessing an Antioxidative Property and Their Inhibitory Effects on Picryl Chloride-Induced Contact Hypersensitivity Reaction
• Pd/C-Catalyzed Chemoselective Hydrogenation in the Presence of a Phenolic MPM Protective Group Using Pyridine as a Catalyst Poison
• Pd/C-catalyzed and Water-mediated Hiyama Cross-coupling Reaction Using an Electron-deficient Phosphine Ligand

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