C. Ramalingan et al. / European Journal of Medicinal Chemistry 41 (2006) 683–696
695
4.1.3.8. 1,3,5-Trimethyl-2,6-diphenylpiperidin-4-one
O-(2-
broth were determined by plating method and adjusted in the
range of 102–105 cfu ml–1. Testing was performed at pH 7.4
0.2. A set of assay tubes containing only inoculated broth
was kept as control and likewise solvent controls were also
run simultaneously. The tubes were incubated in BOD incuba-
tors at ~37 °C for bacteria and ~28 °C for fungi. The minimum
inhibitory concentrations (MICs) were recorded by visual ob-
servations after 24 h (for bacteria) and 72–96 h (for fungi) of
incubation. For the standard, streptomycin (for bacteria) and
amphotericin B (for fungi) were used while DMSO was used
as solvent control.
chlorophenylmethyl)oxime (5h). IR (KBr) (cm–1): 2975, 2965,
2936, 2789 (C–H stretching), 1638 (C=N stretching), 1599,
1
1492 (C=C ring stretching), 752 (N–O stretching). H NMR
(δ ppm): 7.42–7.19 (m, 14H) aryl protons, 5.18 (s, 2H) benzyl
CH2, 3.46–3.39 (m, 1H) H5, 3.34 (d, J = 9.00 Hz, 1H) H6, 3.19
(d, J = 3.90 Hz, 1H) H2, 2.70 – 2.66 (m, 1H) H3, 1.75 (s, 3H)
CH3 at 1, 1.30 (d, J = 7.50 Hz, 3H) CH3 at 5, 1.14 (d, J = 6.90
Hz, 3H) CH3 at 3. GC–MS (m/z): 432 (M+), (M.F:
C27H29ClN2O), 278 (100%).
4.1.3.9. 1-Methyl-2,6-diphenylpiperidin-4-one O-(2-bromophe-
nylmethyl)oxime (5i). IR (KBr) (cm–1): 2966, 2944, 2905,
2847, 2792 (C–H stretching), 1646 (C=N stretching), 1594,
Acknowledgements
1
This work was supported by Korea Research Foundation
Grant (KRF-2004-005-C00006).
1493 (C=C ring stretching), 755 (N–O stretching). H NMR
(δ ppm): 7.55–7.11 (m, 14H) aryl protons, 5.16 (s, 2H) benzyl
CH2, 3.48 (d, J = 14.40 Hz, 1H) H5(eq), 3.25 (1H) H2(ax), 3.19
(dd, J = 11.85 Hz; 3.15 Hz, 1H) H6(ax), 2.52–2.49 (m, 2H)
H2(ax) and H3(ax), 2.20 (1H) H5(ax), 1.78 (s, 3H) CH3 at 1.
GC-MS (m/z): 448 (M+-1), (M.F: C25H25 BrN2O), 207 (100%).
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