H. Liszkiewicz, M. Kowalska, J. Wietrzyk
Nov 1, 2003
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0
Influential Citations
11
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Journal
Indian Journal of Chemistry Section B-organic Chemistry Including Medicinal Chemistry
Abstract
The reaction of 2-aminonicotinic acid hydrazide 1 with carbon disulfide gives 5-(2-amino-3-pyridyl)-2-thioxo-3H-1,3,4-oxadiazole 4 which on treatment with ethyl bromoacctate affords 5-(2-amino-3-pyridyl) -2-ethoxycarbonylthio-1,3,4-oxadiazole 5. Treatment of compound 5 with the appropriate primary and secondary amines provided the corresponding oxadiazole derivatives: alkyl-(cycloalkyl-, aryl)-aminocarbamylmethylthio- 6-10 or alkyl-(cycloalkyl-, aryl)-amino- 11-16. The reaction of 5 with benzylamine furnishes two products: 5-(2-amino-3-pyridyl)-2-benzylamino-1,3,4-oxadiazole 18 and di(benzylcarbamylmethyl)sulfide 19. Selected compounds are tested for their antiproliferative activity in vitro. One of them 19 reveals cytotoxic activity against the cells of 4 human tumor cell lines applied. The ID50 values are in the range of the international activity criterion for synthetic agents (4 μg/mL).