- Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives
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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.
- Ispikoudi, Maria,Amvrazis, Michalis,Kontogiorgis, Christos,Koumbis, Alexandros E.,Litinas, Konstantinos E.,Hadjipavlou-Litina, Dimitra,Fylaktakidou, Konstantina C.
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experimental part
p. 5635 - 5645
(2011/02/22)
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- A convenient synthesis of 5-amino-substituted 1,2,4-oxadiazole derivatives via reactions of amidoximes with carbodiimides
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5-Amino substituted 1,2,4-oxadiazole derivatives were easily prepared, in one step and in high yields, via reactions of a variety of aryl, benzyl, cycloalkyl and alkyl amidoximes with commercially available carbodiimides. Alkyl carbodiimides reacted with amidoximes in toluene to give 5-alkylamino-l,2,4-oxadiazoles, whereas aromatic carbodiimide reacted in DMF to give initially the intermediate O-amidoxime adducts, which were further cyclized to the corresponding 5-arylamino-1,2,4-oxadiazoles.
- Ispikoudi, Maria,Litinas, Konstantinos E.,Fylaktakidou, Konstantina C.
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experimental part
p. 1321 - 1328
(2009/04/11)
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