Synthesis and cytotoxic evaluation of β-alkyl or β-aryl-δ-methyl-α-methylene-δ-lactones. Comparison with the corresponding γ-lactones

Autor:	Wojciech M. Wolf, Jakub Wojciechowski, Lukasz Albrecht, Marek Rozalski, Kazimierz Studzian, Tomasz Janecki, Anna Albrecht, Henryk Krawczyk, Anna Janecka, Urszula Krajewska
Rok vydání:	2010
Předmět:	Pharmacology chemistry.chemical_classification Stereochemistry Aryl Organic Chemistry Horner–Wadsworth–Emmons reaction Formaldehyde General Medicine Chemical synthesis chemistry.chemical_compound chemistry Drug Discovery Michael reaction Methylene Alkyl Lactone
Zdroj:	European Journal of Medicinal Chemistry. 45:710-718
ISSN:	0223-5234
Popis:	We present a simple and general strategy for the synthesis of β,δ-disubstituted-α-methylene-δ-lactones starting from easily available tert-butyl 2-(diethoxyphosphoryl)alk-2-enoates. The elaborated synthetic protocol includes pyrrolidine-catalyzed Michael addition of acetone, diastereoselective reduction of the carbonyl group, lactonization and finally the Horner–Wadsworth–Emmons reaction with formaldehyde. All α-methylene-δ-lactones were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Comparison of cytotoxic activity with corresponding α-methylene-γ-lactones is also discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9895ed9accd5fe8a221d385f19548f4c https://doi.org/10.1016/j.ejmech.2009.11.018 Zobrazit plný text záznamu Full Text from ScienceDirect