Synthesis and Pharmacological Evaluation of Quinoline Derivatives

Abstract

2-chloroquinoline-3-carbaldehyde was synthesized from acetanilide by the action of Vilsmeier-haack reagent. Chlorine group was replaced by methoxy group by methylation at 2nd position of quinoline. 2-methoxyquinoline-3-carbaldehyde was further treated with hydrazine hydrate to form hydrazone of 2-methoxyquinoline which was further treated with different aromatic aldehydes. All the synthesized compounds were characterized by MP, TLC, UV, IR, 1H NMR and Mass spectra. The synthesized compounds were evaluated for anticonvulsant activity at the dose 30 mg/kg by Maximal Electro-Shock-induced (MES) method. Among all synthesized compounds, SVR-A17 showed good anticonvulsant activity. The compounds possessing heteroaromatic moiety groups like pyrrole exhibited good anticonvulsant activity. The antitubercular activity of synthesized compounds was evaluated against Mycobacterium tuberculosis H37Rv. Compound contain thiophen moiety with quinoline Schiff base show good antitubercular activity. Among all compounds SVR- A15 showed significant antitubercular activity. Antibacterial and antifungal activity was carried at 50, 100 and 200 µg/ml. Compounds SVR-A2, SVR-A10 and SVR-A16 exhibited good antimicrobial activity. Newly synthesized compounds possessing electron withdrawing groups like nitro and electron donating groups like methoxy exhibited good antibacterial and antifungal activity. Molecular docking studies showed compound SVR-A17 which have high binding affinity towards binding site and showed good MolDock score.