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Vol. 49, No. 4
Table 6. Spectral Data for Compounds 5
No.
1H-NMR(in DMSO-d6) d (ppm)
5a
5b
5c
1.90—2.00 (4H, m), 2.54 (3H, s), 3.25—3.35 (4H, m), 3.77 (1H, dd, Jϭ9, 6 Hz), 3.90—4.00 (2H, m), 4.09 (1H, t, Jϭ9 Hz), 4.90—5.00 (1H,
m), 6.75 (1H, t, Jϭ9 Hz), 7.08 (1H, dd, Jϭ9, 2.5 Hz), 7.35 (1H, dd, Jϭ16, 2.5 Hz), 10.2 (1H, br s)
1.50—1.60 (2H, m), 1.60—1.70 (4H, m), 2.55 (3H, s), 2.90—3.00 (4H, m), 3.80 (1H, dd, Jϭ9, 6 Hz), 3.90—4.10 (2H, m), 4.12 (1H, t, Jϭ
9 Hz), 4.90—5.00 (1H, m), 7.04 (1H, t, Jϭ9 Hz), 7.15 (1H, dd, Jϭ9, 2.5 Hz), 7.43 (1H, dd, Jϭ14.5, 2.5 Hz), 10.2 (1H, br s)
0.95 (3H, d, Jϭ6.5 Hz), 1.25—1.35 (2H, m), 1.40—1.55 (1H, m), 1.65—1.75 (2H, m), 2.54 (3H, s), 2.60—2.70 (2H, m), 3.20—3.30 (2H,
m), 3.80 (1H, dd, Jϭ9, 6.5 Hz), 3.97 (2H, t, Jϭ5.5 Hz), 4.12 (1H, t, Jϭ9 Hz), 4.90—5.00 (1H, m), 7.04 (1H, t, Jϭ9 Hz), 7.15 (1H, dd, Jϭ9,
2.5 Hz), 7.43 (1H, dd, Jϭ15.5, 2.5 Hz), 10.2 (1H, t, Jϭ5 Hz)
5d
5e
0.89 (3H, t, Jϭ7.5 Hz), 1.20—1.35 (5H, m), 1.74 (2H, d, Jϭ10 Hz), 2.54 (3H, s), 2.61 (2H, t, Jϭ11.5 Hz), 3.29 (2H, d, Jϭ11.5 Hz), 3.80
(1H, dd, Jϭ9, 5.5 Hz), 3.97 (2H, t, Jϭ5.5 Hz), 4.11 (1H, t, Jϭ9 Hz), 4.90—5.00 (1H, m), 7.04 (1H, t, Jϭ9 Hz), 7.15 (1H, dd, Jϭ9, 2.5 Hz),
7.42 (1H, dd, Jϭ15, 2.5 Hz), 10.2 (1H, br s)
1.55—1.65 (2H, m), 1.90—2.00 (2H, m), 2.54 (3H, s), 2.74—2.82 (2H, m), 3.15—3.23 (2H, m), 3.27 (3H, s), 3.29—3.36 (1H, m), 3.80 (1H,
dd, Jϭ9, 6 Hz), 3.97 (2H, t, Jϭ6 Hz), 4.12 (1H, t, Jϭ9 Hz), 4.90—4.98 (1H, m), 7.06 (1H, t, Jϭ9 Hz), 7.15 (1H, dd, Jϭ9, 2.5 Hz), 7.43 (1H,
dd, Jϭ15, 2.5 Hz), 10.2 (1H, br s)
5f
5g
5h
5i
1.50—1.60 (4H, m), 1.70—1.80 (4H, m), 2.54 (3H, s), 3.25—3.35 (4H, m), 3.78 (1H, dd, Jϭ9, 6.5 Hz), 3.97 (2H, t, Jϭ5.5 Hz), 4.09 (1H, t,
Jϭ9 Hz), 4.85—4.95 (1H, m), 6.92 (1H, t, Jϭ9 Hz), 7.09 (1H, dd, Jϭ9, 2.5 Hz), 7.36 (1H, dd, Jϭ16, 2.5 Hz), 10.2 (1H, br s)
2.54 (3H, s), 2.70—2.80 (4H, m), 3.20—3.25 (4H, m), 3.81 (1H, dd, Jϭ9, 6 Hz), 3.98 (2H, t, Jϭ5.5 Hz), 4.12 (1H, t, Jϭ9 Hz), 4.90—5.00
(1H, m), 7.09 (1H, t, Jϭ9 Hz), 7.17 (1H, dd, Jϭ9, 2 Hz), 7.45(1H, dd, Jϭ14.5, 2 Hz), 10.2 (1H, br s)
2.55 (3H, s), 2.67 (4H, t, Jϭ5 Hz), 3.47 (4H, t, Jϭ5 Hz), 3.79 (1H, dd, Jϭ9, 6 Hz), 3.98 (2H, t, Jϭ5 Hz), 4.10 (1H, t, Jϭ9 Hz), 4.85—4.95
(1H, m), 6.95 (2H, d, Jϭ9 Hz), 7.36 (2H, d, Jϭ9 Hz), 10.2 (1H, br s)
2.55 (3H, s), 2.80—2.90 (2H, m), 2.95—3.05 (2H, m), 3.15—3.25 (2H, m), 3.70—3.80 (2H, m), 3.82 (1H, dd, Jϭ9, 6.5 Hz), 3.98 (2H, t, Jϭ
5.5 Hz), 4.13 (1H, t, Jϭ9 Hz), 4.90—5.00 (1H, m), 7.15—7.25 (2H, m), 7.48 (1H, dd, Jϭ14.5, 2.5 Hz), 10.2 (1H, br s)
2.54 (3H, s), 2.97 (4H, t, Jϭ5 Hz), 3.74 (4H, t, Jϭ5 Hz), 3.81 (1H, dd, Jϭ9, 6.5 Hz), 3.98 (2H, t, Jϭ5.5 Hz), 4.13 (1H, t, Jϭ9 Hz), 4.91—
4.97 (1H, m), 7.06 (1H, t, Jϭ9 Hz), 7.18 (1H, dd, Jϭ9, 2.5 Hz), 7.46 (1H, dd, Jϭ15, 2.5 Hz), 10.2 (1H, br s)
5j
of the Japan Society of Chemotherapy.10) The MICs (mg/ml) were deter-
mined by an agar dilution method with Muller–Hinton agar (MHA, Difco
Laboratories, Detroit, Mich). Bacterial suspensions for inocula were pre-
pared by diluting overnight cultures of organisms to give a final concentra-
tion of 106 CFU/ml, and one loopful (5 ml) of an inoculum, corresponding to
about 5ϫ103 CFU per spot was inoculated on drug-containing agar plates.
The plates were incubated for 18—24 h at 37 °C. The MIC was defined as
the lowest drug concentration that prevented visible growth of bacteria.
R. K., Park C-H., Corless P. F., Milller S. J., Rajagopalan P., Wuonola
M. A., McRipley R. J., Eberly V. S., Slee A. M., Forbes M., J. Med.
Chem., 33, 2569—2578 (1990).
5) Park C.-H., Brittelli D. R., Wang C.-L. J., Marsh F. D., Gregory W. A.,
Wuonola M. A., McRipley R. J., Eberly V. S., Slee A. M., Forbes M.,
J. Med. Chem., 35, 1156—1165 (1992); Brickner S. J., Current Phar-
maceutical Design, 2, 175—194, (1996).
6) Calculated log P, pa and pb values were measured by ACD/Labs log P
calculated., ver. 3.0 (Advanced Chemistry Development, Inc.).
7) Some 5-thiocarbonyl oxazolidinones were revealed at the same time
that we synthesized them: Hester J. B., Nidy E. G., Perricone S. C.,
Poel T. J., World Intellectual Property Organization 9854161 (1998)
[Chem. Abstr., 130, 38373q (1999)].
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