当前位置: X-MOL 学术J. Nat. Prod. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Revision of the structure of fagaridine based on the comparison of UV and NMR data of synthetic compounds.
Journal of Natural Products ( IF 3.3 ) Pub Date : 1998 Oct , DOI: 10.1021/np980193s
Takeshi Nakanishi 1 , Masanobu Suzuki 1
Affiliation  

Fagaridine is a quaternary benzo[c]phenanthridine alkaloid, originally isolated from Fagara xanthoxyloides in 1973. The assigned structure of this alkaloid was 7-hydroxy-8-methoxy-5-methyl-2, 3-(methylenedioxy)benzo[c]phenanthridinium (1). We have synthesized this compound, coded NK109, aiming at a practical antitumor drug, and during synthetic studies we questioned the original assigned structure. Thus, we synthesized 8-hydroxy-7-methoxy-5-methyl-2, 3-(methylenedioxy)benzo[c]phenanthridinium (2), isomer of the assigned structure, and compared the spectroscopic data of both 1 and 2. The NMR data of 1 and 2 were very similar, but the UV spectra were completely different. The UV data for fagaridine agreed with these for 2; consequently, the true structure of fagaridine is 2, not 1.

中文翻译:

根据合成化合物的UV和NMR数据比较,对法加替丁进行结构修改。

Fagaridine是季铵基苯并[c]菲啶生物碱,最初于1973年从Fagara黄蒽酮中分离出来。该生物碱的指定结构为7-羟基-8-甲氧基-5-甲基-2,3-(亚甲基二氧基)苯并[c]菲啶鎓(1)。我们已经合成了一种针对NK109的化合物,旨在开发一种实用的抗肿瘤药物,在合成研究过程中,我们对最初指定的结构提出了质疑。因此,我们合成了指定结构的异构体8-羟基-7-甲氧基-5-甲基-2、3-(亚甲基二氧基)苯并[c]菲啶鎓(2),并比较了1和2的光谱数据。 1和2的NMR数据非常相似,但UV光谱完全不同。法加替丁的UV数据与2的一致。因此,法加替丁的真实结构是2,而不是1。
更新日期:2017-01-31
down
wechat
bug