title: Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives.
abstract: 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.
authors.affiliation: Molecular Biology and Genetics Department, Democritus University of Thrace, 68100 Alexandroupolis, Greece.
authors.forename: Maria
authors.initials: M
authors.lastname: Ispikoudi
authors.forename: Michalis
authors.initials: M
authors.lastname: Amvrazis
authors.forename: Christos
authors.initials: C
authors.lastname: Kontogiorgis
authors.forename: Alexandros E
authors.initials: AE
authors.lastname: Koumbis
authors.forename: Konstantinos E
authors.initials: KE
authors.lastname: Litinas
authors.forename: Dimitra
authors.initials: D
authors.lastname: Hadjipavlou-Litina
authors.forename: Konstantina C
authors.initials: KC
authors.lastname: Fylaktakidou
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002351:Carrageenan; D004195:Disease Models, Animal; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy*; D005260:Female; D008084:Lipoxygenase / Q000378:metabolism; D008297:Male; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D011916:Rats, Inbred F344; D013025:Glycine max / Q000201:enzymology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D010069:Oxadiazoles; D002351:Carrageenan; D008084:Lipoxygenase