Back to Search
Start Over
Synthesis and Biological Evaluation of (−) and (+)‐Spiroleucettadine and Analogues
- Source :
- ChemMedChem. 16:1308-1315
- Publication Year :
- 2021
- Publisher :
- Wiley, 2021.
-
Abstract
- A second-generation enantiospecific synthesis of spiroleucettadine is described. The original reported antibacterial activity was not observed when the experiment was repeated on the synthetic samples; however, significant anti-proliferative activity was uncovered for both enantiomers of spiroleucettadine. Comparison of the optical rotational data and ORD-CD spectra of both enantiomers and the reported spectrum from the natural source have not provided a definitive answer regarding the absolute stereochemistry of naturally occurring spiroleucettadine. Efforts then focussed on alteration at the C-4 and C-5 positions of the slightly more active (-)-spiroleucettadine. Ten analogues were synthesised, with three analogues found to possess similar anti-proliferative profiles to spiroleucettadine against the H522 lung cancer cell line.
- Subjects :
- Pharmacology
010405 organic chemistry
Chemistry
Stereochemistry
Spiroleucettadine
Organic Chemistry
Imidazoles
Lung cancer cell line
Total synthesis
Antineoplastic Agents
Stereoisomerism
01 natural sciences
Biochemistry
0104 chemical sciences
010404 medicinal & biomolecular chemistry
Cell Line, Tumor
Drug Discovery
Natural source
Humans
Molecular Medicine
Spiro Compounds
General Pharmacology, Toxicology and Pharmaceutics
Enantiomer
Antibacterial activity
Biological evaluation
Subjects
Details
- ISSN :
- 18607187 and 18607179
- Volume :
- 16
- Database :
- OpenAIRE
- Journal :
- ChemMedChem
- Accession number :
- edsair.doi.dedup.....93e503d1e32e0d748f03355cf4ff99b9