Green synthesis, characterization, and anthelminthic activity of newer quinoline derivatives containing acridine moiety

Abstract

Objectives: Synthesis of newer 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(2-chloro-6-substituted-quinolin-3-yl)-acridine-1,8(2H,5H,9H,10H)-diones were synthesized by reacting 5,5-dimethylcyclohexane-1,3-dione with substituted 2-chloro-quinoline-3-carbaldehyde in presence of ammonium acetate. Methods: Synthesis was carried out by microwave irradiation method and the synthesized compounds have been characterized using elemental analysis, FT-IR, 1H NMR, and 13C NMR spectroscopy and further supported by mass spectroscopy. Purity of all the compounds has been checked on thin layer chromatographic plate and high-performance liquid chromatography technique. All the synthesized compounds were tested for antibacterial and anthelminthic activities. Results: The results were revealed that the compounds AQ-4 and AQ-5 have showed good activity against both Gram-positive and Gram-negative bacteria. Compounds AQ-4 and AQ-5 showed moderate activity against all the organisms. However, all the derivatives have shown less antibacterial activity when compared to the standard drug amikacin. The compounds AQ-3 and AQ-5 showed good anthelminthic activity and compounds AQ-9 and AQ-10 showed moderate anthelminthic activity. However, all the compounds have shown less anthelmintic activity when compared to the standard drug albendazole. Conclusion: The study reveals that compounds containing quinoline derivatives with acridine moiety shown the antibacterial activity against the pathogens Bacillus subtilis, Bacillus cereus, Staphylococcus epidermidis, Salmonella typhi, Pseudomonas aeruginosa and Klebsiella pneumoniae. These derivatives also possess the good anthelmintic activity. The above green synthesis technique could be a right solution for industrial applications in the future and therapeutic needs.