Synthesis of new imidazolyl acetic acid derivatives with anti-inflammatory and analgesic activities

Abstract

We synthesized 2-(4-(4-fluorobenzylidene)-2-(4-fluorophenyl) 5-oxo-4,5-dihydroimidazol-1-yl) acetic acid 3. Chlorination afforded the chloro derivative 4, which reacted with different amines and hydrazine to afford compounds 5-8. Pyrazole, pyrazolone, and thiazolidinone derivatives were also synthesized from Imidazol-1-ylacetic acid hydrazide 8 to give compounds 9-12. Compounds were then evaluated for their anti-inflammatory activity against carrageenan-induced rat paw edema and their analgesic activity using the writhing test in albino mice. Compounds 5, 9, 10, 12 exhibited maximum anti-inflammatory activity, and all the compounds inhibited writhing, with 10 and 12 being two times more effective than the reference standard.

Synthesis of Pyrroles and Condensed Pyrroles as Anti-Inflammatory Agents with Multiple Activities and Their Molecular Docking Study

“…The percentage inhibition of edema thickness at each time interval was calculated from the mean effect in control and treated animals according to the equation [39] [40].…”

Pyrazole Carbohydrazide Derivatives of Pharmaceutical Interest

“…Pyrazolone derivatives are still under investigation [9,10]. In this way, there are some derivatives with a broad spectrum of activities, including antidepressant and anti-inflammatory effects.…”

“…In this way, there are some derivatives with a broad spectrum of activities, including antidepressant and anti-inflammatory effects. 2-{2-[4-(4-Fluorobenzylidene)-2-(4-fluorophenyl)-5-oxo-4,5-dihydroimidazol-1-yl)acetyl}-3-methyl-2,4-dihydro-1 H -pyrazole-5-one ( 3 ) is an effective anti-inflammatory agent in the carrageenan induced rat paw edema test [10] and ethyl 1-(thiophene-2-carbonyl)-4-cyano-5-oxo-2,5-dihydro-1 H -pyrazole-3-carboxylate ( 4 ) showed good antidepressant activity [9]. Interesting, the carbohydrazide moiety can be observed internalized into the heterocyclic nucleus at the core structure of pyrazolones (Figure 1).…”

“…The derivative 5 also exhibited analgesic activity [11]. Only the derivative 9 presented anti-inflammatory activity in the carrageenan induced rat paw edema assay [10]. …”

Facile synthesis, characterisation and anti‐inflammatory activities of ferrocenyl ester derivatives of 4‐arylidene‐5‐imidazolinones

“…Imidazolinones have significant potential as anticonvulsant, anti‐parkinson and anti‐inflammatory agents . These moieties have also been examined for their enzyme inhibition activities, for instance, monoamine oxidase inhibitors, as dual inhibitors of p38α MAPK and ERK1/2 enzymes, as well as angiotensin II receptors . The photochemical phenomena of fluorescent proteins have also been investigated and interpreted by means of these imidazolinones as chemical models …”