Purines. LXIII. Syntheses of azepinomycin, an antitumor antibiotic from Streptomyces species, and its 3-beta-D-ribofuranoside and their 8-imino analogues.
Three variants of a synthetic route to the antitumor antibiotic azepinomycin (3) from 1-substituted N'-alkoxy-5-formamidoimidazole-4-carboxamidine (type 10) are described. The synthesis started with the monocytes 10a-c and proceeded through the intermediates 11a-c, 12a-c, 13a-c, 14a-c, and 4a, b and 3-beta-D-ribofuranosylazepinomycin (4c). The benzyl version (series a), including the permutation 14a-->15-->3, was found to produce the antibiotic (3) most efficiently. The starting materials 10a-c were readily prepared from the 9-substituted adenines 7a-c via the N-oxides 8a-c and the 1-alkoxy derivatives 9a-c. The 8-amino analogues (17 and 18) of 3 and 4c were also synthesized from 12a and 12c, respectively.
Fujii
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Faculty of Pharmaceutical Sciences, Kanazawa University, Japan.
Saito
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Fujisawa
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D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D001381:Azepines / Q000138:chemical synthesis*; D007097:Imines / Q000138:chemical synthesis; D013267:Stilbenes; D013302:Streptomyces / Q000378:metabolism*
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D001381:Azepines; D007097:Imines; D013267:Stilbenes; C054359:azepinomycin 3-ribofuranoside; C089060:8-iminoazepinomycin 3-ribofuranoside; C054358:azepinomycin