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1 Polish Journal of Chemistry

1 1999

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Synthesis and pharmacological properties of new derivatives of 2-amino-5-(2-amino-3-pyridyl)-1,3,4-oxadiazole

Liszkiewicz H., Głowiak T., Kowalska M., Rutkowska M., Szeląg A., Barczyńska J., Kędzierska-Goździk L., Błaszczyk F., Dziewiszek W.

Polish Journal of Chemistry

1999

vol. 73 nr 2

321-332

Reaction of 2-aminonicotinic acid hydrazide with cyanogens bromide allowed to obtain 2-amino-5-(2-amino-3-pyridyl)-1,3,4-oxadiazole (2), which with 2- or 3-chloropropionyl chloride and 4-chlorobutyryl chloride gave 5-(2-amino-3-pyridyl)-2-(2-chloroproprionylamino)-1,3,4-oxadiazole (5), 5-(2-amino-3-pyridyl)-2-(3-chloroproprionyl- amino)-1,3,4-oxadiazole (6) and 5-(2-amino-3-pyridyl)-2-(4-chlorobutyrylamino)-1,3,4-oxadiazole (7), respectively. Cyclization of chloroacyl derivative 7 led to 5-(2-amino-3-pyridyl)-2-(2-oxo-1-pyrrolidinyl)-1,3,4-oxadiazole (9). Treatment of oxadiazole 2 with appropriate alkylating agents (1,3-dibromopropane or 1,4-dibromobutane) gave 2-azetidynyl-1,3,4-oxadiazole (10) or 2-pyrrolidynyl-1,3,4-oxadiazole (11). Compounds 3,4,7,10 and 11 were tested towards a psychotropic activity. Compound 10 showed anxiolytic properties and an antiserotonin action, which was confirmed in the test of the black-white box and the m-CPP test, respectively. Crystal structure was determined on a single crystal.