Synthesis and antitumor activity of amino derivatives of pyridine-2-carboxaldehyde thiosemicarbazone

摘要: Various substituted pyridine-2-carboxaldehyde thiosemicarbazones (12 compounds) have been synthesized and evaluated for antineoplastic activity in mice bearing the L1210 leukemia. Oxidation of 3-nitro-2-picoline,5-nitro-2-picoline,3-nitro-2,4-lutidine, 5-nitro-2,4-lutidine with selenium dioxide was employed to generate corresponding pyridine-2-carboxaldehydes, which were then converted cyclic ethylene acetals subsequently reduced amino hydroxyamino derivatives by catalytic hydrogenation. Condensation nitro aldehydes thiosemicarbazide afforded respective thiosemicarbazones. Acetylation alkylsulfonation 5-amino acetal, followed condensation yield amide The most active compounds 3-aminopyridine-2-carboxaldehyde thiosemicarbazone 3-amino-4-methylpyridine-2-carboxaldehyde produced against leukemia, % T/C values 246 255, 40% 60-day long-term survivors at two daily doses 40 mg/kg 10 mg/kg, respectively, six consecutive days.