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