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Synthesis and SAR studies of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potent anti-tumor agents.

Abstract
A series of phenanthroindolizidine and phenanthroquinolizidine alkaloids and their 14-amino-derivatives (1-44) were prepared and systematically evaluated for their anti-tumor activities against A549 and HL60 cell lines. The bioassay results showed that most of these alkaloids possess good anti-tumor activities. Especially, compounds 15, 22, 28, 33-36, 40 and 42 displayed low nanomolar or subnanomolar levels of anti-tumor activity. The configuration of (13aS,14S)-14-hydroxyphenanthroindolizidines and (14aR,15R)-15-hydroxyphenanthroquinolizidines was confirmed to be optimal. 14-Amino-phenanthroindolizidines with increased polarity possess good anti-tumor activity, especially for compounds 26 and 28. Most of the phenanthroquinolizidine alkaloids exhibited higher anti-tumor activity than that of phenanthroindolizidine alkaloids. Our present study provides fundamental support for development and optimization of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potential anti-tumor drugs.
AuthorsZiwen Wang, Meng Wu, Yi Wang, Zheng Li, Lei Wang, Guifang Han, Fazhong Chen, Yuxiu Liu, Kailiang Wang, Ao Zhang, Linghua Meng, Qingmin Wang
JournalEuropean journal of medicinal chemistry (Eur J Med Chem) Vol. 51 Pg. 250-8 (May 2012) ISSN: 1768-3254 [Electronic] France
PMID22417638 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2012 Elsevier Masson SAS. All rights reserved.
Chemical References
  • Alkaloids
  • Antineoplastic Agents
  • Indolizines
  • Phenanthrolines
  • Quinolizines
  • phenanthroindolizidine
  • phenanthroquinolizidine
Topics
  • Alkaloids (chemical synthesis, chemistry, pharmacology)
  • Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
  • Cell Line, Tumor
  • Chemistry Techniques, Synthetic
  • Humans
  • Indolizines (chemistry)
  • Phenanthrolines (chemistry)
  • Quinolizines (chemistry)
  • Structure-Activity Relationship

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