Eldisine,Lilly ,France,1980
ChEBI: Vindesine is a vinca alkaloid, a methyl ester, an organic heterotetracyclic compound, an organic heteropentacyclic compound, a tertiary alcohol, a tertiary amino compound and a primary carboxamide. It has a role as an antineoplastic agent. It is functionally related to a vincaleukoblastine.
About 10 g of VLB (vincaleucoblastine or simply vinblastine) sulfate were
converted by standard procedures to VLB free base. The free base, obtained
as a residue after evaporation of the dried ethereal solvent, was dissolved in
about 200 ml of anhydrous methanol. Anhydrous liquid ammonia (300 ml)
was added, and the reaction mixture sealed and maintained at about 100°C
for 60 hours. The reaction vessel was opened, and the contents removed and
evaporated to dryness in vacuo. The resulting residue, containing 4-desacetyI
VLB C-3 carboxamide, as shown by thin layer chromatography, were combined
and the solvent evaporated therefrom in vacuo, yielding asa residue purified
4-desacetyl VLB C-3 carboxamide free base. The NMR and IR spectra of the
solid free base confirmed the structure indicated. The free base showed a
band in the infrared at 1,687 cm -l , characteristic of the amide function. The
molecular weight of the free base determined by mass spectroscopy was 753
which is in agreement with theoretical value calculated for C 43 H 55 N 5 O 7 .
