Wednesday , 19 June 2024

Synthesis, Characterization, Biological Evaluation and Docking studies of 2-(benzyl sulfonyl)-5-(3-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl)-1,3,4-oxadiazole Derivatives

G. Govindu*, D. Rajesh, P. Raveendra Reddy, L.K. Ravindranath
Department of chemistry, Sri Krishnadevaraya University, Anantapuramu, A.P-India

New novel derivatives of 2-((4- substituted benzyl)sulfonyl)-5-(3-(4-( substituted phenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl)-1,3,4-oxadiazoles  (9a-l as per scheme-I)were prepared by condensation of 2-(4-hydrazinylpyrimidin-5-yl)-5-((4-substituted benzyl)sulfonyl)-1,3,4-oxadiazole (8a-f) with various 4-substituted benzoic acids. The synthon 8a-f were obtained by the refluxing of 2-(4-chloropyrimidin-5-yl)-5-((4-substituted benzyl)sulfonyl)-1,3,4-oxadiazole (7a-f)  with hydrazine hydrate in presence of ethanol. The synthon 7a-f were obtained through chlorination of 5-(5-((4-subsitututed benzyl)sulfonyl)-1,3,4-oxadiazol-2-yl)pyrimidin-4-ol (6a-f)  in presence of POCl3. The synthon 6a-f were obtained from 5-(5-((4-subsitututed benzyl)thio)-1,3,4-oxadiazol-2-yl)pyrimidin-4-ol (5a-f) in presence of H2O2/ Glacial acetic acid. The synthon 5a-f were obtained from the reaction between 5-(4-hydroxypyrimidin-5-yl)-1,3,4-oxadiazole-2(3H)-thione (3) and various aromatic halogenated compounds (4a-f) in presence of KOH and ethanol.  The synthon were obtained from the condensation of 4-hydroxypyrimidine-5-carbohydrazide (2) with carbon disulphide in presence of base. The compound 2 were obtained from the condensation of ethyl 4-hydroxy pyrimidine-5-carboxylate (1) with hydrazine hydrate in presence of ethanol. All the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and elemental analysis. The newly synthesized compounds were subjected to various biological studies both antibacterial and antifungal including docking studies for model compounds.
Keywords: pyrimidine, 1,2,4-triazole, 1,3,4-oxadiazole, POCl3, Biological and Docking studies.

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