Extension of the Library of
Biologically Active γ-Alkylidene Butenolides

Petr Novák; Milan Pour; Marcel Špulák; Ivan Votruba; Martin Kotora

doi:10.1055/s-0028-1083181

PAPER

Extension of the Library of Biologically Active γ-Alkylidene Butenolides

Petr Novák^a, Milan Pour^b, Marcel Špulák^b, Ivan Votruba^c, Martin Kotora*^a,c
^a Department of Organic and Nuclear Chemistry and Centre for New Antivirals and Antineoplastics, Faculty of Science, Charles University, Hlavova 8, 128 43 Praha 2, Czech Republic
Fax: +420(2)21951326; e-Mail: kotora@natur.cuni.cz;
^b Centre for New Antivirals and Antineoplastics, Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
^c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Praha 6, Czech Republic

Abstract

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Abstract

γ-Alkylidene butenolides bearing a deoxyriboside, a steroid, and a metallocene moiety were synthesized by stereoselective sequential cross-coupling lactonization procedure from the corresponding functionalized terminal alkynes with 3-iodopropenoic acids. The high selectivity of the butenolide ring formation was secured by the Pd/Cu salt ratio. The resulting compounds were tested for antifungal and cytostatic properties. Most notably, γ-alkylidene butenolides bearing deoxyriboside moiety showed promising cytostatic activity in the micromolar range.

Key words

cross-coupling - lactones - catalysis - antitumor agents - palladium

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