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

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 exhibited potent inhibition activity in three human...

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Veröffentlicht in:Organic & biomolecular chemistry 2006-01, Vol.4 (5), p.860-867
Hauptverfasser: Chuang, Ta-Hsien, Lee, Shiow-Ju, Yang, Cheng-Wei, Wu, Pei-Lin
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Sprache:eng
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Zusammenfassung: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 exhibited potent inhibition activity in three human cancer cell lines, with IC(50) 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b516152e