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Synthesis and antifungal activity of 5-(3,5-diphenylpyrazol-4-yloxymethyl)-2-(4-oxo-2-substituted phenyl-3-thiazolidinyl)-1,3,4-oxadiazoles/thiadiazoles and related compounds
Dubey, Anand Kumar,Sangwan, Naresh K.
, p. 1043 - 1047 (2007/10/02)
Treatment of ethyl (3,5-diphenylpyrazol-4-yloxy)acetate (1) with hydrazine followed by condensation of the resulting hydrazide 2 with araldehydes gives the corresponding Schiff bases (3-5).Cyclization of 2 with aromatic acids in refluxing phosphorus oxychloride yields 2-aryl-5-(3,5-diphenylpyrazol-4-yloxymethyl)-1,3,4-oxadiazoles (6-8).Treatment of 2 with carbon disulphide and potassium hydroxide followed by cyclization of the resulting 2-(dithiocarboxy)hydrazide monopotassium salt (9) with hydrazine gives 5-(3,5-diphenylpyrazol-4-yloxymethyl)-1,3,4-thiadiazole-2(3H)-thione (10). (3,5-Diphenylpyrazol-4-yloxy)acetic acid 2-(aminothioxomethyl)hydrazide (11), prepared by treatment of 2 with potassium thiocyanate and aqueous hydrochloric acid, yields 2-amino-5-(3,5-diphenylpyrazol-4-yloxymethyl)-1,3,4-oxadiazole (12) and the corresponding thiadiazole 13 when treated with potassium iodide/iodine and conc. sulphuric acid, respectively.Condensation of 12 and 13 with araldehydes affords the corresponding Schiff bases (14-17).Cyclization of 14-17 with mercaptoacetic acid furnishes the title compounds, 5-(3,5-diphenylpyrazol-4-yloxymethyl)-2-(4-oxo-2-substituted phenyl-3-thiazolidinyl)-1,3,4-oxadiazoles/thiadiazoles (18-21).Several compounds show promising antifungal activity against tested phytopathogenic fungi.The most active compounds are 2 and 5 against F. oxysporum (MIC 6.25 μg ml-1), 6 and 19 against C. capsicum (MIC 6.25 μg ml-1) and 18 and 20 against R. solani (MIC 3.13 μg ml-1).
