Abstract
The lupane-type triterpene betulin (1) has been subjected to a series of structural modifications for the purpose of evaluating resultant cancer cell growth inhibitory activity. The reaction sequence 7 11 12 was especially noteworthy in providing a betulin-derived amine dimer. Other unexpected synthetic results included the 11 and 13/1417 conversions, which yielded an imidazo derivative. X-ray crystal structures of dimer 12 and intermediate 25 are reported. All of the betulin modifications were examined for anticancer activity against the P388 murine and human cell lines. Significant cancer cell growth inhibition was found for 4, 8, 9, 15/16, 19, 20, 24, and 26, which further defines the utility of the betulin scaffold.
Original language | English (US) |
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Pages (from-to) | 863-872 |
Number of pages | 10 |
Journal | Journal of Natural Products |
Volume | 77 |
Issue number | 4 |
DOIs | |
State | Published - Apr 25 2014 |
ASJC Scopus subject areas
- Analytical Chemistry
- Molecular Medicine
- Pharmacology
- Pharmaceutical Science
- Drug Discovery
- Complementary and alternative medicine
- Organic Chemistry
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CCDC 971646: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Melody, N. (Creator), Hempenstall, F. (Creator), Chapuis, J. (Creator), Groy, T. L. (Creator), Williams, L. (Creator) & Pettit, G. R. (Creator), The Cambridge Structural Database, 2014
DOI: 10.5517/cc11m2f5, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc11m2f5&sid=DataCite
Dataset
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CCDC 971647: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Melody, N. (Creator), Hempenstall, F. (Creator), Chapuis, J. (Creator), Groy, T. L. (Creator), Williams, L. (Creator) & Pettit, G. R. (Creator), The Cambridge Structural Database, 2014
DOI: 10.5517/cc11m2g6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc11m2g6&sid=DataCite
Dataset