New methods of synthesis of methylglyoxal bis-guanylhydrazone (as bis-hydrochloride) and methylglyoxal bis-thiosemicarbazone are developed, which are based on the reactions of 2-ethoxypropenal with aminoguanidine and thiosemicarbazide in an acid medium.
Methylglyoxal thiosemicarbazones are known to possess carcinostatic properties [1,2], but no compounds of this class containing unsubstituted NH 2 group have been reported until now. Direct interaction of methylglyoxal with thiosemicarbazide exhibits variable character and leads to the formation of compounds having different structures, among which monothiosemicarbazone is found in very insignificant amounts [3]. in continuation of the search for new antitumor agents among methylglyoxal thiosemicarbazones, we have studied the hydrolysis of 2-ethoxypropenal thiosernicarbazone obtained previously [4] and the interaction of the resulting methylglyoxal thiosemicarbazone with copper salts.Hydrolysis of 2-ethoxypropenal thiosemicarbazone at pH 2 and a temperature of 50 -60~ proceeds without rupture of the C=N bond and leads to the formation of methylglyoxal thiosemicarbazone (MGTSC):
MGTSCAs is known, the carcinostatic properties of thiosemicarbazones increase upon their complexation with transition metals: the complexes are more lipophilic and readily penetrate into cells, possess a greater association constant, and may serve as a base for attaching a cytotoxic ligand [5]. In connection with this, we have studied the formation of complexes between MGTSC and copper(I) chloride (Cu-MGTSC):
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