title: 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.
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.
authors.affiliation: Laboratorio de Química Orgánica y Biomolecular, Universidad Industrial de Santander, Cra 27 calle 9, Bucaramanga A.A. 678, Colombia.
authors.forename: Carlos E
authors.initials: CE
authors.lastname: Puerto Galvis
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Kouznetsov
mesh_terms: D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D003500:Cyclization; D004305:Dose-Response Relationship, Drug; D047108:Embryonic Development / Q000187:drug effects*; D005663:Furans / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D008301:Maleimides / Q000737:chemistry*; D023421:Models, Animal; D015394:Molecular Structure; D010641:Phenotype; D013329:Structure-Activity Relationship; D015027:Zebrafish / Q000196:embryology* / Q000235:genetics
chemical_list: C584687:7-oxa-2-azabicyclo(2.2.1)hept-5-ene; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005663:Furans; D008301:Maleimides; C439622:furfurylamine