PUBLICATION
An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model
- Authors
- Puerto Galvis, C.E., and Kouznetsov, V.V.
- ID
- ZDB-PUB-121206-13
- Date
- 2013
- Source
- Organic & biomolecular chemistry 11(3): 407-411 (Journal)
- Registered Authors
- Keywords
- none
- MeSH Terms
-
- Animals
- Bridged Bicyclo Compounds, Heterocyclic/chemical synthesis
- Bridged Bicyclo Compounds, Heterocyclic/chemistry
- Bridged Bicyclo Compounds, Heterocyclic/pharmacology*
- Bridged Bicyclo Compounds, Heterocyclic/toxicity
- Cyclization
- Dose-Response Relationship, Drug
- Embryonic Development/drug effects*
- Furans/chemistry*
- Inhibitory Concentration 50
- Maleimides/chemistry*
- Models, Animal*
- Molecular Structure
- Phenotype
- Structure-Activity Relationship
- Zebrafish/embryology*
- Zebrafish/genetics
- PubMed
- 23192531 Full text @ Org. Biomol. Chem.
Citation
Puerto Galvis, C.E., and Kouznetsov, V.V. (2013) An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model. Organic & biomolecular chemistry. 11(3):407-411.
Abstract
An unexpected intramolecular cyclization during the reaction of furfurylamine with maleimides is reported as a novel strategy for the efficient green synthesis of the 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton. Under the same reaction conditions, 7-oxabicyclo[2.2.1]hept-5-enes were synthesized when furfurylamine was N-protected by the acetyl group. Both types of bicycloheptenes were screened using the zebrafish model system for genetics and developmental biology.
Errata / Notes
Comment.
Genes / Markers
Expression
Phenotype
Mutations / Transgenics
Human Disease / Model
Sequence Targeting Reagents
Fish
Orthology
Engineered Foreign Genes
Mapping