Issue 5, 2006
From the journal:

Organic & Biomolecular Chemistry

Expedient synthesis and structure–activity relationships of phenanthroindolizidine and phenanthroquinolizidine alkaloids

Ta-Hsien Chuang,a   Shiow-Ju Lee,b   Cheng-Wei Yangb  and  Pei-Lin Wu*ac  

* Corresponding authors

a Department of Chemistry, National Cheng Kung University, Tainan, Taiwan, ROC
E-mail: wupl@mail.ncku.edu.tw
Fax: 886-6-2740552

b Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Miaoli, Taiwan, ROC

c Department of Cosmetic Science, Chung Hwa College of Medical Technology, Tainan, Taiwan, ROC

Abstract

The total synthesis of alkaloids phenanthroindolizidine 1a, tylophorine 1b, and phenanthroquinolizidine 1c, has been achieved in 46%, 49%, and 42% overall yield, respectively, starting from the corresponding phenanthrene-9-carboxaldehyde. Compound 1c exhibited potent inhibition activity in three human cancer cell lines, with IC50 values ranging from 104 to 130 nM. The structure–activity relations of these alkaloids and some of their synthetic intermediates against the three cell lines were also described.

Graphical abstract: Expedient synthesis and structure–activity relationships of phenanthroindolizidine and phenanthroquinolizidine alkaloids

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Article information

DOI
https://doi.org/10.1039/B516152E
Article type
Paper
Submitted
14 Nov 2005
Accepted
16 Dec 2005
First published
18 Jan 2006

Org. Biomol. Chem., 2006,4, 860-867

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Expedient synthesis and structure–activity relationships of phenanthroindolizidine and phenanthroquinolizidine alkaloids

T. Chuang, S. Lee, C. Yang and P. Wu, Org. Biomol. Chem., 2006, 4, 860 DOI: 10.1039/B516152E

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