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Syntheses and Biological Activities of the LMNO, ent-LMNO, and NOPQR(S) Ring Systems of Maitotoxin
- Source :
- The Journal of organic chemistry. 82(18)
- Publication Year :
- 2017
-
Abstract
- Structure–activity relationship studies of maitotoxin (MTX), a marine natural product produced by an epiphytic dinoflagellate, were conducted using chemically synthesized model compounds corresponding to the partial structures of MTX. Both enantiomers of the LMNO ring system were synthesized via aldol reaction of the LM ring aldehyde and the NO ring ketone. These fragments were derived from a common cis-fused pyranopyran intermediate prepared through a sequence involving Nozaki–Hiyama–Kishi reaction, intramolecular oxa-Michael addition, and Pummerer rearrangement. The NOPQR(S) ring system, in which the original seven-membered S ring was substituted with a six-membered ring, was also synthesized through the coupling of the QR(S) ring alkyne and the NO ring aldehyde and the construction of the P ring via 1,4-reduction, dehydration, and hydroboration. The inhibitory activities of the synthetic specimens against MTX-induced Ca2+ influx were evaluated. The LMNO ring system and its enantiomer induced 36 and 18%...
- Subjects :
- Stereochemistry
Molecular Conformation
Alkyne
010402 general chemistry
Ring (chemistry)
Nitric Oxide
01 natural sciences
Aldehyde
chemistry.chemical_compound
Aldol reaction
Animals
Pyrans
chemistry.chemical_classification
Maitotoxin
Aldehydes
Dose-Response Relationship, Drug
010405 organic chemistry
Pummerer rearrangement
Organic Chemistry
Oxocins
Stereoisomerism
Glioma
P ring
Ketones
0104 chemical sciences
Rats
Hydroboration
chemistry
Calcium
Marine Toxins
Subjects
Details
- ISSN :
- 15206904
- Volume :
- 82
- Issue :
- 18
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....a27501eee6afb81043ec1ad4df25fc1f