A two-step synthesis of cytostatically active benzo[c]phenanthridine derivatives.
A two-step synthesis of cytostatically active benzo[c]phenanthridine derivatives.
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DOI：
10.1002/anie.200461969
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发表时间：
2005-01
影响因子：
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通讯作者：
B. Clement;M. Weide;Ulrich Wolschendorf;Ilka Kock
中科院分区：
文献类型：
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作者：
B. Clement;M. Weide;Ulrich Wolschendorf;Ilka Kock
苯并[c]菲菲啶类物质具有多种药理性质。文献中提到了大量天然存在的生物碱，它们含有苯并[c]菲菲啶环体系，并具有已知的活性谱。[1,2]除了这类天然产物中最重要的代表fagaronine(1)外，其他具有广泛药理潜力的生物碱有nitidine(2)、chelerythrine(3)和sanguinarine (4; Scheme 1)[3 - 5]。这些天然产物的合成引起了人们的极大兴趣，因为它们只能从植物材料中极少量地分离出来。Cushman等等。[6]描述了从花椒和fagara系列品种中分离2的产率在0.003 ~ 0.07%之间。化合物1于1972年首次从花椒Fagara zanthoxyloides根中分离得到。1974年，Gillespie等人首次报道了1的全合成该合成路线以2,3 -二甲氧基-5-硝基萘为起始原料，产率为0.7%。石井等人、[9]Treus等人、[4]Lunch等人、[5]和Š midrkal[10]等人也描述了到1的其他合成途径，后者仅为a
The benzo [c] phenanthridine class of substances display a variety of pharmacological properties. A large number of naturally occurring alkaloids that contain a benzo [c] phenanthridine ring system and have a known spectrum of activity are mentioned in the literature.[1, 2] Aside from fagaronine (1), the most important representative of this group of natural products, other alkaloids with extensive pharmacological potential are nitidine (2), chelerythrine (3), and sanguinarine (4; Scheme 1).[3–5] The synthesis of these natural products is of great interest, because they can be isolated from plant materials only in very small amounts. Cushman etal.[6] describe yields in the 0.003 to 0.07% range for the isolation of 2 from a series of zanthoxylum and fagara varieties. Compound 1 was first isolated from the root of Fagara zanthoxyloides in 1972.[7]The first total synthesis of 1 was described by Gillespie et al. in 1974.[8] This synthetic route gave 1 in 0.7% yield starting from 2, 3-dimethoxy-5-nitronaphthalene. Other synthetic routes to 1 have been described by Ishii et al.,[9] Treus et al.,[4] Lunch et al.,[5] and Š midrkal [10], the latter being only a