Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives

• Published in: Bioorganic & medicinal chemistry 2006-07, Vol.14 (13), p.4657-4663
• Main Authors: Sondhi, Sham M., Dinodia, Monica, Kumar, Ashok
• Format: Article
• Language: English
• Subjects: Amidines; Amidines - chemical synthesis; Amidines - chemistry; Amidines - pharmacology; Analgesic; Analgesics; Analgesics - chemical synthesis; Analgesics - chemistry; Analgesics - pharmacology; Animals; Anti-inflammatory; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis; Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; Biological and medical sciences; Biological Assay; Bones, joints and connective tissue. Antiinflammatory agents; Female; Hydrazones; Hydrazones - chemical synthesis; Hydrazones - chemistry; Hydrazones - pharmacology; Medical sciences; Mice; Neuropharmacology; Pharmacology. Drug treatments; Rats
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2006.02.014

A number of amidine derivatives ( 3a– i) were synthesized by condensation of cyanopyridine and cyanopyrazine with sulfonylhydrazides in the presence of sodium methoxide. 2-Acetylpyridine and 4-acetylpyridine were condensed with sulfonylhydrazides by microwave irradiation in solid phase to give corresponding hydrazones ( 5a– d). Indole-3-carboxaldehyde was condensed with sulfonylhydrazides by refluxing in acetic acid to give corresponding condensation products ( 5e and f). Anti-inflammatory activity evaluation was carried out using carrageenin-induced paw oedema assay and compounds 3e, f and 5e exhibited good anti-inflammatory activity. Analgesic activity evaluation was carried out using acetic acid writhing assay and compounds 3a, c, e and 5f showed good analgesic activity. A number of amidine derivatives ( 3a– i) were synthesized by condensation of cyanopyridine and cyanopyrazine with sulfonylhydrazides in the presence of sodium methoxide. 2-Acetylpyridine and 4-acetylpyridine were condensed with sulfonylhydrazides by microwave irradiation in solid phase to give corresponding hydrazones ( 5a– d). Indole-3-carboxaldehyde was condensed with sulfonylhydrazides by refluxing in acetic acid to give corresponding condensation product ( 5e and f). All the compounds, that is, 3a– i and 5a– f were purified by crystallization or by column chromatography. Structures of all the synthesized compounds are supported by correct IR, 1H NMR, mass spectral and analytical data. Anti-inflammatory activity evaluation was carried out using carrageenin-induced paw oedema assay and compounds 3e, f and 5e exhibited good anti-inflammatory activity, that is 52%, 37% and 38% at 50 mg/kg po, respectively. Analgesic activity evaluation was carried out using acetic acid writhing assay and compounds 3a, c, e and 5f showed good analgesic activity, that is, 50%, 50%, 50% and 60% at 50 mg/kg po, respectively.