Conversion of Natural Narciclasine to Its C-1 and C-6 Derivatives and Their Antitumor Activity Evaluation: Some Unusual Chemistry of Narciclasine.
Molecules
; 27(13)2022 Jun 28.
Article
in En
| MEDLINE
| ID: mdl-35807391
ABSTRACT
During the search for a general, efficient route toward the synthesis of C-1 analogues of narciclasine, natural narciclasine was protected and converted to its C-1 enol derivative using a novel semi-synthetic route. Attempted conversion of this material to its triflate in order to conduct cross-coupling at C-1 resulted in a triflate at C-6 that was successfully coupled with several functionalities. Four novel compounds were fully deprotected after seven steps and subjected to evaluation for cytotoxic activity against three cancer cell lines. Only one derivative showed moderate activity compared to that of narciclasine. Spectral and physical data are provided for all new compounds.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Amaryllidaceae Alkaloids
/
Neoplasms
/
Antineoplastic Agents
Limits:
Humans
Language:
En
Journal:
Molecules
Year:
2022
Document type:
Article