Studies on new cyclic imides obtained from aminophenazone with analgesic properties. Potent effects of a 3,4-dichloromaleimide derivative.
This paper describes the synthesis of new cyclic imides obtained by reaction with aminophenazone (CAS 58-15-1, 4-aminoantipyrine) and different anhydrides with further cyclization with acetic acid under reflux. Their structures were confirmed by spectral data (IR and NMR) and elemental analysis. The analgesic activity of the synthesized compounds was investigated initially with the writhing test in mice and the most promising compound, a 3,4-dichloromaleimide derivative (3), was analyzed using other models of nociception. The results indicated that compound 3 exerts potent analgesic activity in mice, being more active than some reference drugs. The analgesia caused by this compound was not reversed by naloxone in the writhing test. In the hotplate test, compound 3 did not increase the latency period of pain induced by thermal stimuli, confirming that it does not interact with opioid systems.
Núcleo de Investigações Químico-Farmacêuticas (NIQFAR), Curso de Farmácia, Universidade do Vale do Itajaí, Itajaí, SC, Brazil.
Fátima
F
de Campos
Rogério
R
Corrêa
Márcia Maria
MM
de Souza
Rosendo Augusto
RA
Yunes
Ricardo José
RJ
Nunes
Valdir
V
Cechinel-Filho
D019342:Acetic Acid; D000632:Aminopyrine / Q000031:analogs & derivatives* / Q000494:pharmacology*; D018712:Analgesics, Non-Narcotic / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D002211:Capsaicin; D005557:Formaldehyde; D007094:Imides / Q000138:chemical synthesis* / Q000494:pharmacology*; D007202:Indicators and Reagents; D008297:Male; D051379:Mice; D009270:Naloxone / Q000494:pharmacology; D009292:Narcotic Antagonists / Q000494:pharmacology; D010146:Pain / Q000188:drug therapy / Q000517:prevention & control; D010147:Pain Measurement / Q000187:drug effects; D010538:Peritonitis / Q000139:chemically induced / Q000517:prevention & control; D011930:Reaction Time / Q000187:drug effects; D013329:Structure-Activity Relationship
D018712:Analgesics, Non-Narcotic; D007094:Imides; D007202:Indicators and Reagents; D009292:Narcotic Antagonists; D000632:Aminopyrine; D005557:Formaldehyde; D009270:Naloxone; D019342:Acetic Acid; D002211:Capsaicin