SYNTHESIS OF PYRROLIZIDINE ALKALOIDS INDICINE, INTERMEDINE, LYCOPSAMINE, AND ANALOGS AND THEIR N-OXIDES - POTENTIAL ANTITUMOR AGENTS
SYNTHESIS OF PYRROLIZIDINE ALKALOIDS INDICINE, INTERMEDINE, LYCOPSAMINE, AND ANALOGS AND THEIR N-OXIDES - POTENTIAL ANTITUMOR AGENTS
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DOI：
10.1021/jm00383a001
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发表时间：
1985-01-01
影响因子：
7.3
通讯作者：
GORDON, MM
中科院分区：
文献类型：
--
作者：
ZALKOW, LH;GLINSKI, JA;GORDON, MM
(-)-合成了（+）-络石烷酸、（-）-和（+）-绿二花酸，并将它们的异亚丙基衍生物与从猪屎豆中分离的野百合碱水解得到的（-）-反枝黄花碱在C-9位置特异性偶联。水解后再氧化，分别得到靛果碱、中间体、石蒜胺的N-氧化物和新的非天然产物。在P388淋巴细胞白血病系统中，与吲哚辛N-氧化物同时筛选这些类似物，并比较结果。制备了其他相关类似物，并进行了类似的筛选，并将结果与来自indicine N-氧化物的结果进行了比较。
(-)- and (+)-trachelanthic and (-)- and (+)-viridifloric acids were synthesized and their isopropylidene derivatives were regiospecifically coupled, at C-9, with (-)-retronecine obtained by hydrolysis of monocrotaline, isolated from Crotalaria spectabilis. Hydrolysis, followed by oxidation, led to the N-oxides of indicine, intermedine, lycopsamine and the new nonnatural product, respectively. Each of these analogs was screened in the P388 lymphocytic leukemia system at the same time as indicine N-oxide, and the results were compared. Other related analogs were prepared and similarly screened, and the results compared with those from indicine N-oxide.