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.
Ispikoudi
Maria
M
Molecular Biology and Genetics Department, Democritus University of Thrace, 68100 Alexandroupolis, Greece.
Amvrazis
Michalis
M
Kontogiorgis
Christos
C
Koumbis
Alexandros E
AE
Litinas
Konstantinos E
KE
Hadjipavlou-Litina
Dimitra
D
Fylaktakidou
Konstantina C
KC
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
D000894:Anti-Inflammatory Agents, Non-Steroidal; D010069:Oxadiazoles; D002351:Carrageenan; D008084:Lipoxygenase