Abstract
A series of secondary amines (4–19) containing 2-chloroquinoline as lipophilic domain have been synthesized based on the structural requirements essential for allylamine/benzylamine antimycotics by nucleophilic substitution reaction of 3-chloromethyl-2-chloroquinoline 3 with various aliphatic and aromatic amines in absolute ethanol in the presence of triethylamine. Some N-methyl derivatives (20–25) were also synthesized by N-methylation using (CH3)2SO4/NaH. The structures of newly synthesized compounds were established by the combined use of IR, 1H-NMR, 13C-NMR, and Mass spectra. Compounds 4–25 were screened in vitro at conc. of 200 g/ml for their antifungal activity against Aspergillus niger MTCC 281, Aspergillus flavus MTCC 277, Monascus purpureus MTCC 369, and Penicillium citrinum NCIM 768 by cup-plate method using Terbinafine as a references drug. Among the secondary amines, compounds 4, 5, 8, 10, 14, and 16 exhibited potential antifungal activity and their corresponding N-methyl (20–25) derivatives also showed further increase in antifungal activity against fungal strain Aspergillus niger MTCC 281, Aspergillus flavus MTCC 277. Compounds 3-chloro-N-[(2-chloroquinolin-3-yl)methyl]-4-fluoro-N-methylaniline (24) and 3,4-dichloro-N-[(2-chloroquinolin-3-yl)methyl]-N-methylaniline (25) were the most potent derivatives of the series.
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The author (SK) is thankful to the University Grant Commission (UGC), New Delhi, India, for the award of UGC-JRF. The authors are also thankful to Department of pharmaceutical chemistry, faculty of pharmacy, Jamia Hamdard for providing necessary facility and CDRI, Lucknow, India for recording FAB-MS spectral data.
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Kumar, S., Bawa, S., Drabu, S. et al. Design and synthesis of 2-chloroquinoline derivatives as non-azoles antimycotic agents. Med Chem Res 20, 1340–1348 (2011). https://doi.org/10.1007/s00044-010-9463-6
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DOI: https://doi.org/10.1007/s00044-010-9463-6