Abstract
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, (1)H 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 (IC(50)=4.6 microM) and CDK-1(IC(50)=7.4 microM) and compound 3a showed moderate CDK-5 inhibitory activity (IC(50)=7.5 microM). The other compounds showed moderate anti-inflammatory and analgesic activities.
MeSH terms
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Analgesics / chemical synthesis*
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Analgesics / chemistry
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Analgesics / pharmacology
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Animals
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Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
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Anti-Inflammatory Agents, Non-Steroidal / chemistry
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology
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Benzimidazoles / chemical synthesis*
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Benzimidazoles / chemistry
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Benzimidazoles / pharmacology
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Benzoxazoles / chemical synthesis*
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Benzoxazoles / chemistry
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Benzoxazoles / pharmacology
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CDC2 Protein Kinase / drug effects
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Cyclin-Dependent Kinase 5 / drug effects
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Drug Evaluation, Preclinical / methods
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Enzyme Activation / drug effects
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Female
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Glycogen Synthase Kinase 3 / drug effects
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Mice
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Protein Kinases / drug effects*
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Rats
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Rats, Wistar
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Schiff Bases / chemistry
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Structure-Activity Relationship
Substances
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Analgesics
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Anti-Inflammatory Agents, Non-Steroidal
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Benzimidazoles
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Benzoxazoles
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Schiff Bases
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benzimidazole
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Protein Kinases
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Cyclin-Dependent Kinase 5
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CDC2 Protein Kinase
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Glycogen Synthase Kinase 3