Twenty-one derivatives of 8-hydroxyquinoline (oxine, 8H, CAS 148-24-3) were prepared and characterized by UV, IR, MS and NMR spectroscopy. Four of these derivatives, N-butyl, 8-butyloxyquinolinium bromide (HBD), 8-pentyloxyquinoline (HPEM), N-pentyl, 8-pentyloxyquinolinium bromide (HPED) and N-benzyl, 8-benzyloxy quinolinium chloride (HBED) are new and reported for the first time. The antimicrobial activity of these compounds was carried out in vitro against 11 Gram positive and 18 Gram negative bacteria, and 18 fungi including 9 dermatophytes, 7 other filamentous fungi and 2 Candida species. Three compounds namely, HPRD, HPED and HBED were found to possess significant antibacterial activity in order of HPED > HPRD > HBED, whereas 4 were found to possess significant antifungal activity in order of 8H > HT > HPEM > 8B.
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