Collect. Czech. Chem. Commun. 2009, 74, 1161-1178
Published online 2009-07-24 10:06:36

Cytostatic tetrazole–butenolide conjugates: linking tetrazole and butenolide rings via stille coupling and biological activity of the target substances

Vojtěch Balšáneka, Lucie Tichotováb, Jiří Kunešb, Marcel Špulákb, Milan Pourb,*, Ivan Votrubac and Vladimír Buchtad

a RE&D VUFB Ltd., Poděbradská 56/186, 180 66 Prague 9, Czech Republic
b Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 03 Hradec Králové, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
d Department of Clinical Microbiology, University Hospital, Sokolská 581, 500 05 Hradec Králové, Czech Republic


A series of tetrazoles linked to the butenolide core via benzene rings were prepared by the Stille coupling reaction of α-(tributylstannyl)butenolides and 5-(alkylsulfanyl)-1-(4-iodophenyl)tetrazoles, and the compounds were tested for antifungal and cytostatic activity. Interesting antifungal activities against the filamentous strain Absidia corymbifera, and cytostatic activities against leukemic cells HL-60 and CCRF-CEM were found. The cytostatic activity requires the presence of both the butenolide ring and the alkylsulfanyl group bound to tetrazole ring. In addition, the feasibility of Pd-coupling reactions with 5-iodotetrazoles was evaluated.

Keywords: Pd catalysis; Cross-coupling reactions; Heterocycles; Tetrazoles; Butenolides; Dihydrofuranes; Antifungals; Biological activity.

References: 22 live references.