Fujii T, Saito T, Fujisawa T
Faculty of Pharmaceutical Sciences, Kanazawa University, Japan.
Chem Pharm Bull (Tokyo). 1994 Jun;42(6):1231-7. doi: 10.1248/cpb.42.1231.
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.
描述了从1-取代的N'-烷氧基-5-甲酰胺基咪唑-4-甲脒（10型）合成抗肿瘤抗生素氮杂环庚三烯霉素（3）的三种合成路线变体。合成从单核体10a-c开始，经过中间体11a-c、12a-c、13a-c、14a-c以及4a、b和3-β-D-呋喃核糖基氮杂环庚三烯霉素（4c）。发现苄基变体（a系列），包括置换14a→15→3，能最有效地产生抗生素（3）。起始原料10a-c可通过9-取代腺嘌呤7a-c经N-氧化物8a-c和1-烷氧基衍生物9a-c轻松制备。3和4c的8-氨基类似物（17和18）也分别由12a和12c合成。
