ACCEPTED MANUSCRIPT
(400 MHz, DMSO) δ 8.26 (t, J = 5.8 Hz, 1H), 7.72 (s, 1H), 7.66 (d, J = 8.4 Hz, 2H), 7.63-7.52 (m, 4H), 7.42 (dd,
J = 8.6, 2.0 Hz, 1H), 4.77 (dd, J = 8.6, 6.0 Hz, 1H), 4.17 (t, J = 9.0 Hz, 1H), 3.79 (dd, J = 9.1, 6.5 Hz, 1H), 3.44 (t,
J = 5.4 Hz, 2H), 3.32-3.24 (m,4H), 3.20-3.12 (m, 4H), 2.78 (s, 6H), 1.85 (s, 3H).
5.1.33N-{3-{2-fluoro-4'-[(4-hydroxyacetylpiperazin-1-yl)iminomethyl]-biphenyl-4-yl}-2-oxo-1,3-oxazolidine-5-(S)
-ylmethyl}-acetamide (10t)
Compound 10t was prepared from compound 9f and glycolic acide in the same manner as described for 10r.
Yellow solid; yield: 77 %; M.p.: 225-227 ºC; MS (ESI) m/z (%): 498.7[M+H]+; 1H-NMR (600 MHz, DMSO-d6):
8.27 (s, 1H), 7.75 (s, 1H), 7.68 (d, J = 7.9 Hz, 2H), 7.64-7.53 (m, 4H), 7.42 (d, J = 7.9 Hz, 1H), 4.78 (s, 1H), 4.67
(d, J = 7.9 Hz, 1H), 4.17 (dd, J = 17.5, 6.8 Hz, 3H), 3.85-3.75 (m, 1H), 3.67 (s, 2H), 3.55 (s, 2H), 3.45 (s, 2H),
3.17 (d, J = 18.3 Hz, 4H), 1.86 (s, 3H). 13C-NMR (151 MHz, DMSO): δ 170.48, 170.42, 160.21, 158.58, 154.37,
139.70, 139.63, 135.81, 134.43, 131.06, 129.96, 129.08, 126.39, 122.86, 122.78, 114.34, 106.04, 105.85, 72.15,
60.55, 51.22, 50.92, 47.56, 43.02, 41.78, 40.82, 22.83.
5.1.34N-{3-{2-fluoro-4'-[(4-aminoacetylpiperazin-1-yl)iminomethyl]-biphenyl-4-yl}-2-oxo-1,3-oxazolidine-5-(S)-y
lmethyl}-acetamide (10u)
Compound 10u was prepared from compound 9f and glycine in the same manner as described for 10r. White
solid; yield: 78%; M.p.: 222-223 ºC; MS (ESI) m/z (%): 497.5[M+H]+; 1H-NMR (600 MHz, DMSO) δ 8.29 (s,
1H), 7.76 (s, 1H), 7.67 (d, J = 7.6 Hz, 2H), 7.58 (dd, J = 26.6, 8.4 Hz, 4H), 7.42 (d, J = 8.3 Hz, 1H), 6.30 (s, 2H),
4.77 (s, 1H), 4.17 (t, J = 8.6 Hz, 1H), 3.85-3.77 (m, 1H), 3.71 (s, 4H), 3.57 (s, 2H), 3.44 (s, 2H), 3.21 (s, 2H), 3.16
(s,2H), 1.85 (s, 3H).
5.1.35N-{3-{2-fluoro-4'-[(4-methanesulfonylpiperazin-1-yl)iminomethyl]-biphenyl-4-yl}-2-oxo-1,3-oxazolidine-5-(
S)-ylmethyl}-acetamide (11a)
Compound 11a was prepared from compound 9f and methanesulfonyl chloride in the same manner as described
for 10a. Yellow solid; yield: 79 %; M.p.: 258-260 ºC; MS (ESI) m/z (%): 517.8 [M+H]+; 1H-NMR (600 MHz,
DMSO) δ 8.26 (t, J = 5.8 Hz, 1H), 7.77 (s,1H), 7.68 (d, J = 8.3 Hz, 2H), 7.62-7.54 (m, 4H), 7.42 (dd, J = 8.6, 1.9
Hz, 1H), 4.77 (td, J = 11.4, 5.4 Hz, 1H), 4.17 (t, J = 9.0 Hz, 1H), 3.79 (dd, J = 9.0, 6.5 Hz, 1H), 3.44 (t, J = 5.4 Hz,
2H), 3.32-3.29 (m,4H), 3.29-3.25 (m, 4H), 2.95 (s,3H), 1.85 (s, 3H).
5.1.36N-{3-{2-fluoro-4'-[(4-benzylpiperazin-1-yl)iminomethyl]-biphenyl-4-yl}-2-oxo-1,3-oxazolidine-5-(S)-ylmeth
yl}-acetamide (11b)
To the mixture of compound 9f (0.3 g, 0.68 mmol) and CsCO3(0.45 g, 1.36 mmol) in DMF (5 mL) was added
benzyl bromide (0.17 g, 1.02 mmol), Then the resulted mixture was stirred for 4 h at 25 °C. After completion of
the reaction as indicated by TLC, water (10 mL) was added. The resulting precipitate was filtered, washed with
water and dried to get a white solid in 72 % yield. M.p.: 213-215 ºC; MS (ESI) m/z (%):530.5 [M+H]+; 1H-NMR
(400 MHz, DMSO) δ 8.26 (t, J = 5.8 Hz, 1H), 7.70-7.50 (m, 7H), 7.41 (dd, J = 8.6, 1.8 Hz, 1H), 7.34 (d, J = 4.0
Hz, 4H), 7.30-7.23 (m, 1H), 4.76 (dt, J = 11.4, 5.5 Hz, 1H), 4.17 (t, J = 9.0 Hz, 1H), 3.79 (dd, J = 9.1, 6.5 Hz, 1H),
3.54 (s, 2H), 3.44 (t, J = 5.4 Hz, 2H), 3.15 (s, 4H), 2.60-2.53 (m, 4H), 1.84 (s, 3H).
5.1.37N-{3-{2-fluoro-4'-[(4-allylpiperazin-1-yl)iminomethyl]-biphenyl-4-yl}-2-oxo-1,3-oxazolidine-5-(S)-ylmeth
yl}-acetamide (11c)
Compound 11c was prepared from compound 9f and allyl bromide in the same manner as described for 11b.
Yellow solid; yield: 79 %. M.p.: 234-235 ºC; MS (ESI) m/z (%): 480.4 [M+H]+; 1H-NMR (400 MHz, DMSO) δ
8.26 (t, J = 5.8 Hz, 1H), 7.65 (d, J = 8.1 Hz,3H), 7.62-7.56 (m, 2H), 7.54 (d, J = 7.4 Hz,2H), 7.41 (dd, J = 8.6, 2.0
Hz, 1H), 5.95-5.74 (m, 2H), 5.19 (dd, J = 22.8, 13.8 Hz, 1H), 4.76 (dt, J = 11.5, 5.6 Hz, 1H), 4.17 (t, J = 9.0 Hz,