7-deoxypancratistatin has been researched along with aziridine* in 1 studies
1 other study(ies) available for 7-deoxypancratistatin and aziridine
| Article | Year |
|---|---|
Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.
An efficient synthesis of C-1 derivatives of 7-deoxypancratistatin is reported. The key steps include the following: selective opening of an epoxide with aluminum acetylide in the presence of an aziridine; solid-state silica-gel-catalyzed opening of an aziridine; and oxidative cleavage of a phenanthrene core and its recyclization to phenanthridone to provide the key C-1 aldehyde 22. The conversion of this aldehyde to C-1 acetoxymethyl and C-1 hydroxymethyl derivatives is described along with the evaluation of their biological activity against several cancer cell lines and in an apoptosis study. The C-1 acetoxymethyl derivative has shown promising activity comparable to that of the natural product. In addition, a total synthesis of trans-dihydrolycoricidine and a formal total synthesis of 7-deoxypancratistatin are reported from aldehyde 22. Detailed experimental and spectral data are provided for all new compounds. Topics: Aldehydes; Amaryllidaceae Alkaloids; Antineoplastic Agents, Phytogenic; Apoptosis; Aziridines; Catalysis; Cell Line, Tumor; Cyclization; Drug Screening Assays, Antitumor; Epoxy Compounds; Humans; Isoquinolines; Molecular Structure; Oxidation-Reduction; Phenanthrenes; Stereoisomerism; Structure-Activity Relationship | 2010 |