Collect. Czech. Chem. Commun. 1995, 60, 1242-1246

Synthesis of Monomeric 2-[(2-Methyl-2-propenoyl)oxy]ethyl Esters of Prostaglandins

Jaroslav Palečeka and Ivan Veselýb

a Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic
b Development Division, Spolana Chemical Works, 277 11 Neratovice, Czech Republic


This paper describes a new synthesis of monomeric 2-/(2-methyl-2-propenoyl)oxy/ethyl esters of prostaglandins (IIa-IId). The monomeric esters were prepared by reaction of an alkali metal or triethylammonium salt of a prostaglandin of the F2a or A2 series (Ia-Id) with 2-iodoethyl (IIIa) or 2-bromoethyl-2-methyl-2-propenoate (IIIb) in good to high yields. These monomers have been used for preparing reversible anchoring of prostaglandins on a modified three-dimensional biocompatible hydrogels prepared by copolymerization with 2-hydroxyethyl 2-methyl-2-propenoate. The application of functionalized polymers could be used in drug forms with controlled liberation of biologically active PG derivatives.