Abstract
A general, improved procedure for rapid synthesis of philanthotoxin analogues, a pharmacologically important class of polyamine conjugates, is described. The solution-phase procedure is illustrated by gram-scale synthesis of philanthotoxins PhTX-343 and PhTX-12. Selectively protected polyamines are coupled to N(alpha)-Fmoc-protected amino acid pentafluorophenyl esters. After removal of the N(alpha)-Fmoc group, the amine is coupled with carboxylic acid pentafluorophenyl esters. Deprotection followed by a rapid and efficient purification by vacuum liquid chromatography on octadecylsilyl silica (RP-18 phase) gave the philanthotoxin analogues in 74-78% overall yield.
| Original language | English |
|---|---|
| Journal | European Journal of Medicinal Chemistry |
| Volume | 38 |
| Issue number | 1 |
| Pages (from-to) | 117-22 |
| Number of pages | 6 |
| ISSN | 0223-5234 |
| Publication status | Published - 2003 |
Keywords
- Chromatography, Liquid
- Combinatorial Chemistry Techniques
- Electrophoresis, Capillary
- Magnetic Resonance Spectroscopy
- Models, Chemical
- Phenols
- Polyamines
- Silica Gel
- Silicon Dioxide
- Solutions
- Tyrosine