4-Hydroxy-3-quinolinecarboxamides with antiarthritic and analgesic activities

Abstract

A series of 4-hydroxy-3-quinolinecarboxamides has been synthesized and evaluated by the oral route as antiinflammatory agents in carrageenin-induced foot edema and adjuvant-induced arthritis and as analgesic agents in the acetic acid induced writhing test. Among the most active molecules, some have shown both analgesic and acute antiinflammatory activities. Others, such as compounds 24, 37, and 52, were only powerful peripherally acting analgesics. Compound 52, being active at 1 mg/kg (ED50), is the most potent compound in the series. Some analogues, substituted in the 2-position by an alcohol, ester, or amine function, displayed potent antiarthritic activity in the same range as that of piroxicam and were also active in acute tests of inflammation and nociception. They inhibited the activity of both cyclooxygenase and 5-lipoxygenase at micromolar concentrations. Compound 102 (RU 43526) showed potent antiarthritic activity (adjuvant-induced arthritis, ED50 = 0.7 mg/kg, po) and gastrointestinal tolerance (ED100 greater than 250 mg/kg, po) and thus it is presently undergoing an extensive pharmacological evaluation.

Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

“…Other uses of heterocyclic compounds containing nitrogen and sulfur include manufacturing biocides, dyes [22][23][24], and plant-growth regulators [25]. Thus, the synthesis of thiazole and thiadiazole derivatives is currently of great importance to the scientific community.…”

Quinoline Derivatives: In Vitro Antimicrobial Study

“…Literature survey shows that various quinoline derivatives are known to possess a wide range of pharmacological properties, such as antiviral [14] , antitubercular [15] , antidiabetic [16] , antibacterial [17] , anticancer [18] , antiarthritic, analgesic [19] antiinflammatory [20] , antioxidant [21] etc. Owing to their interesting biological properties, in the present work some novel quinoline derivatives were synthesized from arylidine, dimidone and ammonium acetate.…”

Efficient one-pot synthesis of ethyl 2-substitued-4-methylthiazole-5-carboxylates

“…2-Amino-1,3-thiazoles ring system (7) has found application in drug development for the treatment of allergies (8), hypertension (9), inflammation (10,11), schizophrenia (12), and bacterial (13) and HIV (14) infections. Especially, ethyl 2-amino-4-methylthiazole-5-carboxylate (4a) and its 2-substituted derivatives are building blocks in organic synthesis especially in the preparation of biologically important and medicinally useful agents (15,16), of which 4a is also an intermediate for synthesis of 4-methyl-5-formylthiazole, a key intermediate for cefditoren pivoxil (17)(18)(19).…”