Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives

We describe herein a convenient straightforward synthesis of 5-amino-substituted 1,2,4-oxadiazoles, upon the reactions of amidoximes with carbodiimides, as well as their further derivatization to acetamides, in good yields. Most of the compounds exhibited in general low interaction with the stable radical 1,1-diphenyl-2-picryl-hydrazyl. Compounds 32 and 39 inhibited significantly soybean lipoxygenase. Selected compounds were screened for their in vivo anti-inflammatory activity using the carrageenin paw edema model and showed significant anti-inflammatory activity (26, 51%). The ability of the compounds to release NO in the presence of a thiol factor has been also investigated.

5-Amino substituted 1,2,4-oxadiazole derivatives were easily prepared, in one step and in high yields, upon the reactions of a variety of amidoximes with carbodiimides. Subsequent acetylation provided the corresponding acetamides. A number of compounds exhibited significant in vivo anti-inflammatory activity (up to 51%).Figure optionsDownload as PowerPoint slide