Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff’s bases

A series of N-(acridin-9-yl)-4-(benzo[d]imidazol/oxazol-2-yl) benzamides has been synthesized by the condensation of 9-aminoacridine derivatives with benzimidazole or benzoxazole derivatives. Condensation of 2-hydroxy naphthaldehyde with functionalized diamines leads to the formation of Schiff’s bases and not imidazole derivatives. All these compounds were characterized by correct FT-IR, 1H NMR, MS and elemental analyses. These compounds were screened for anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activities. Compounds 11 and 7e(f) showed good anti-inflammatory (35.8% at 50 mg/kg po) activity and good analgesic activity (60% at 50 mg/kg po), respectively. Compound 3b showed significant in vitro activity against CDK-5 (IC50 = 4.6 μM) and CDK-1(IC50 = 7.4 μM) and compound 3a showed moderate CDK-5 inhibitory activity (IC50 = 7.5 μM). The other compounds showed moderate anti-inflammatory and analgesic activities.

A series of N-(acridin-9-yl)-4-(benzo[d]imidazol/oxazol-2-yl)benzamides (3a–f) has been synthesized by the condensation of 9-aminoacridine derivatives with benzimidazole or benzoxazole derivatives. Schiff’s bases 7a–e(f), 9 and 11 were synthesized by microwave irradiation. Compounds 3a–f, 7a–e(f) and 11 were evaluated for anti-inflammatory and analgesic activities. Kinase inhibition assays for all these compounds were carried out against CDK-1, CDK-5 and GSK-3.Figure optionsDownload as PowerPoint slide