Chemistry of acronycine, XI. Rearrangement of dihydronoracronycine to dihydroisonoracronycine-mechanistic studies.
Chemistry of acronycine, XI. Rearrangement of dihydronoracronycine to dihydroisonoracronycine-mechanistic studies.
复制标题
Acronycine 的化学，XI。
DOI：
10.1021/np50042a009
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发表时间：
1985
影响因子：
5.1
通讯作者：
Cordell,GA
中科院分区：
文献类型：
--
作者：
Funayama,S;Cordell,GA
二氢去甲鸦片碱 (3) 重排为二氢异鸦片碱 (4) 是通过分子间反应而不是最初设想的分子内反应进行的。氘标记研究表明，氘在二氢异鸦片碱的 C3、C12 和双甲基位置处掺入 (4)。因为当以与 3 相同的方式处理双诺衍生物时没有发生反应，看来色烯偕甲基对于重排的发生很重要。 Acronycine (1)，一种半萜吖啶酮生物碱，从 Baurella simplicifolia (Endl.) Hartley (芸香科) (2-8)（新南威尔士州本土的澳大利亚灌木梣木）的树皮中分离出来 和昆士兰，拥有迄今为止测试的所有生物碱中最广泛的体内抗肿瘤活性（9-12）。然而，对于 1 或其简单衍生物（如 2）的化学或作用方式知之甚少。我们之前报道过，如果二氢去甲鸦片碱 (3) 溶解在 98%
The rearrangement of dihydronoracronycine (3) to dihydroisonoracronycine (4) proceeds by way of an intermolecular reaction rather than an intramolecular reaction as had originally been supposed. Deuterium-labeling studies showed the incorporation of deuterium at C3, C12, and thegeminal methyl positions of dihydroisonoracronycine (4). Because no reaction occurred when the bisnor derivative was treated in the same manner as 3, it appears that the chromene geminal methyl groups are important forthe rearrangement to occur.Acronycine (1), a hemiterpene acridone alkaloid isolated from the bark of Baurella simplicifolia (Endl.) Hartley (Rutaceae)(2-8), the Australian scrub ash indigenous to New South Wales and Queensland, possesses the broadest spectrum of in vivo an-tineoplastic activityof any alkaloid thusfar tested (9-12). However, relatively little is known of the chemistry or mode of action of 1 or its simple derivatives such as 2. We previously reported that if dihydronoracronycine (3) was dissolved in 98%