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Nucleosides and nucleotides 179. Ring-expanded purine nucleosides. The synthesis and cytotoxicity of imidazo[4,5-c]azepine nucleosides

✍ Scribed by Noriaki Minakawa; Takuma Sasaki; Akira Matsuda

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
649 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

The synthesis of ring-expanded imidazo [4,5-c]azepine nucleosides (3-6) is described. Treatment of 5-iodoimidazole derivative 9 with methyl acrylate in the presence of a palladium catalyst gave (E)-5-(2-carbomethoxyvinyl)-1-(2,3,5-tri-O-acetyl-13-Dribofuranosyl)imidazole-4-carboxamide (10), appropriate manipulation of which gave 1-I~-D-ribofuranosyl-l,5-dihydroimidazo[4,5-c]azepin-4,6-dione (3). The ring-expanded guanosine derivative 4 was prepared in a manner similar to the synthesis of 3. The ringexpanded inosine derivatives 5 and 6 were obtained from 6-acetoxy-l-(2,3,5-tri-Oacetyl-13-D-ribofuranosyl)-5,6-dihydroimidazo[4,5-c]azepin-4(IH)-one (21) through palladium-catalyzed hydrogenolysis. The cytotoxicity of these ring-expanded nucleosides is also described.

📜 SIMILAR VOLUMES

ChemInform Abstract: Nucleosides and Nuc
ChemInform Abstract: Nucleosides and Nucleotides. Part 179. Ring-Expanded Purine Nucleosides. The Synthesis and Cytotoxicity of Imidazo[4,5-c]azepine Nucleosides.
✍ N. MINAKAWA; T. SASAKI; A. MATSUDA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 39 KB 👁 2 views

Nucleosides and Nucleotides. Part 179. Ring-Expanded Purine Nucleosides. The Synthesis and Cytotoxicity of Imidazo[4,5-c]azepine Nucleosides. -Title compounds (V), (IX), (XVIII), and (XIX) are prepared and tested for cytotoxic activity. Only (XVIII) shows small activity.

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