Syntéza prekursorů biologicky aktivních laktonů I

• Main Author: Bémová, Hana
• Other Authors: Kučerová, Marta
• Format: Dissertation
• Language: Czech
• Published: 2008
• Online Access: http://www.nusl.cz/ntk/nusl-292469

Charles University in Prague, Faculty of Pharmacy in Hradec Kralove Department of Pharmaceutical Chemistry and Drug Control SYNTHESIS OF PRECURSORS FOR BIOLOGICALLY ACTIVE LACTONES I. Diploma Thesis Hana Bemova A number of unsaturated five membered lactones from the family of 2,5-dihydrofuran-2- ones exert high biological activity, effecting cytotoxic, antifungal or antiviral, for example. The search of this diploma thesis resumes synthetic derivates of 2,5-dihydrofuran-2-ones with antineoplastic activity. Within this project two novel methyl (Z)- and two methyl (E)-5-aryl-2-brompent-2-en-4- ynoates were prepared by Sonogashira couplings methyl dihalogenpropiolates (E- and Z-isomers were developed by bromination of methyl propiolate) with arylethynes - phenylacetylene and 4­ethynyl­N,N­dimethylaniline. Apart from the side product of homocoupling, β-monoalkynylated products were obtained in these reactions. A dialkynylated product was isolated in high yield (about 90 %) from the reaction with double phenylacetylene. All prepared substances can serve as precursors for various other coumpounds. The acids prepared by hydrolysis of methyl (E)-5-aryl-2-brompent-2-en-4-ynoates will be used for the lactonization into 5-alkyliden-2,5-dihydrofuran-2-ones. The target compounds containing group of γ-butyrolactone will...