734
J. Vinšová et al. / Bioorg. Med. Chem. 22 (2014) 728–737
d, J = 6.1 Hz, CHAHB), 16.01 (2C, d, J = 6.5 Hz, CH3). Anal. Calcd for C18-
H18BrF3NO5P (496.21): C, 43.57; H, 3.66; N, 2.82. Found: C, 43.23; H,
3.50; N, 2.49.
4.1.1.10.
oyl}phenyl diethyl phosphate (1j).
mp 75 °C; IR (ATR): 1686 (amide I), 1617 (
(amide II), 1494, 1479, (
CC aromatic) cmꢀ1
4-Chloro-2-{[3-(trifluoromethyl)phenyl]carbam-
Yield: 42%, white solid;
CC aromatic), 1565
1H NMR (CDCl3,
m
m
;
300 MHz): d 9.75 (1H, br s, NH), 8.06 (1H, br s, H20), 7.96 (1H, m,
H40), 7.91 (1H, dd, J = 2.7 Hz, J = 1.0 Hz, H3), 7.47 (1H, t, J = 8.2 Hz,
H50), 7.44 (1H, dd, J = 8.8 Hz, J = 2.7 Hz, H5), 7.40 (1H, m, H60),
7.30 (1H, dd, J = 8.8 Hz, J = 1.4 Hz, H6), 4.30–4.16 (4H, m, CHAHB),
1.34 (6H, td, J = 7.1 Hz, J = 1.2 Hz, CH3); 13C NMR (CDCl3,
75 MHz): d 162.12, 145.24 (1C, d, J = 6.9 Hz), 138.68, 132.32 (1C,
d, J = 1.8 Hz), 131.79 (1C, d, J = 1.9 Hz), 131.59, 131.39 (1C, q,
J = 32.2 Hz, C30), 129.56, 129.25 (1C, d, J = 5.7 Hz), 123.85 (1C, q,
J = 270.8 Hz, CF3), 122.94, 122.79 (1C, d, J = 2.3 Hz), 121.01 (1C, q,
J = 3.8 Hz, C20), 116.57 (1C, q, J = 4.0 Hz, C40), 65.79 (2C, d,
J = 6.1 Hz, CHAHB), 16.02 (2C, d, J = 6.4 Hz, CH3). Anal. Calcd for C17-
H18BrFNO5P (451.76): C, 47.86; H, 4.02; N, 3.10. Found: C, 47.53; H,
4.36; N, 3.24.
4.1.1.6.
4-Bromo-2-{[4-(trifluoromethyl)phenyl]carbam-
oyl}phenyl diethyl phosphate (1f).
Yield: 52%, white solid;
mCC aromatic), 1544(amide
mp70 °C;IR (ATR): 1698(amide I), 1605 (
II), 1479 (m
CC aromatic) cmꢀ1; 1H NMR (CDCl3, 300 MHz): d 9.76 (1H,
br s, NH), 8.05 (1H, m, H3), 7.93–7.84 (2H, m, H30,H50), 7.66–7.56 (2H,
m, H20, H60), 7.60 (1H, dd, J = 8.8 Hz, J = 2.7 Hz, H5), 7.23 (1H, dd,
J = 8.8 Hz, J = 1.4 Hz, H6), 4.32–4.13 (4H, m, CHAHB), 1.34 (6H, td,
J = 7.1 Hz, J = 1.2 Hz, CH3); 13C NMR (CDCl3, 75 MHz): d 162.08,
145.73 (1C, d, J = 7.0 Hz), 141.15, 135.33 (1C, d, J = 1.8 Hz), 134.58
(1C, d, J = 1.2 Hz), 129.65 (1C, d, J = 5.6 Hz), 123.16 (1C, d, J = 2.3 Hz),
126.26 (2C, q, J = 3.8 Hz, C30, C50), 126.24 (1C, q, J = 32.5 Hz, C40),
124.07 (1C, q, J = 269.9 Hz, CF3), 119.56, 119.32 (1C, d, J = 2.0 Hz),
65.81 (2C, d, J = 6.1 Hz, CHAHB), 16.05 (2C, d, J = 6.4 Hz, CH3). Anal.
Calcd for C18H18BrF3NO5P (496.21): C, 43.57; H, 3.66; N, 2.82. Found:
C, 43.44; H, 3.26; N, 2.92.
4.1.1.11.
diethyl phosphate (1k).
IR (ATR): 1674 (amide I), 1609 (
1493 (
CC aromatic) cmꢀ1 1H NMR (CDCl3, 500 MHz): d 9.57
4-Chloro-2-[(4-chlorophenyl)carbamoyl]phenyl
Yield: 54%, white solid; mp 71 °C;
CC aromatic), 1546 (amide II),
m
4.1.1.7. 4-Bromo-2-[(3-bromophenyl)carbamoyl]phenyl diethyl
m
;
phosphate (1g).
1682 (amide I), 1629, 1593 (
CC aromatic) cmꢀ1 1H NMR (CDCl3, 300 MHz): d 9.54 (1H, br s,
Yield: 74%, white solid; mp 85 °C; IR (ATR):
(1H, br s, NH), 7.89 (1H, d, J = 2.7 Hz, H3), 7.75–7.68 (2H, m, H20,
H60), 7.42 (1H, dd, J = 8.8 Hz, J = 2.7 Hz, H5), 7.35–7.29 (2H, m,
H30, H50), 7.28 (1H, dd, J = 8.8 Hz, J = 1.2 Hz, H6), 4.28–4.15 (4H,
m, CHAHB), 1.33 (6H, t, J = 7.2 Hz, CH3); 13C NMR (CDCl3,
125 MHz): d 161.84, 145.15 (1C, d, J = 7.0 Hz), 136.71, 132.13 (1C,
d, J = 1.7 Hz), 131.74 (1C, d, J = 1.9 Hz), 131.52, 129.50 (1C, d,
J = 5.7 Hz), 129.45, 129.02, 122.73 (1C, d, J = 2.3 Hz), 121.05,
65.72 (2C, d, J = 6.3 Hz, CHAHB), 16.04 (2C, d, J = 6.4 Hz, CH3). Anal.
Calcd for C17H18Cl2NO5P (418.21): C, 48.82; H, 4.34; N, 3.35. Found:
C, 49.05; H, 4.24; N, 3.45.
m
CC aromatic), 1543 (amide II), 1480
(m
;
NH), 8.04 (1H, d, J = 2.8 Hz, H3), 8.01 (1H, t, J = 1.9 Hz, H20), 7.64
(1H, m), 7.58 (1H, dd, J = 8.8 Hz, J = 2.7 Hz, H5), 7.32–7.17 (3H, m),
4.32–4.13 (4H, m, CHAHB), 1.35 (6H, td, J = 7.1 Hz, J = 1.0 Hz, CH3);
13C NMR (CDCl3, 75 MHz): d 161.80, 145.77 (1C, d, J = 7.0 Hz),
139.34, 135.21, 134.51, 130.29, 129.59 (1C, d, J = 5.9 Hz), 127.50,
123.03 (1C, d, J = 2.3 Hz), 122.73, 122.64, 119.22 (1C, d, J = 2.0 Hz),
118.33, 65.76 (2C, d, J = 6.0 Hz, CHAHB), 16.06 (2C, d, J = 6.5 Hz,
CH3). Anal. Calcd for C17H18Br2NO5P (507.11): C, 40.26; H, 3.58; N,
2.76. Found: C, 40.10; H, 3.33; N, 2.58.
4.1.1.12. 4-Chloro-2-[(3-fluorophenyl)carbamoyl]phenyl diethyl
phosphate (1l).
1678 (amide I), 1612 (
1482 (
CC aromatic) cmꢀ1
Yield: 64%, white solid; mp 86 °C; IR (ATR):
CC aromatic), 1552 (amide II), 1491,
1H NMR (CDCl3, 300 MHz): d 9.60
4.1.1.8. 4-Bromo-2-[(4-bromophenyl)carbamoyl]phenyl diethyl
m
phosphate (1h).
1676 (amide I), 1606 (
1481 (
CC aromatic) cmꢀ1
Yield: 48%, white solid; mp 68 °C; IR (ATR):
CC aromatic), 1544 (amide II), 1489,
1H NMR (CDCl3, 300 MHz): d 9.54
m
;
m
(1H, br s, NH), 7.90 (1H, dd, J = 2.7 Hz, J = 1.0 Hz, H3), 7.71 (1H,
dt, J = 10.9 Hz, J = 2.3 Hz, H20), 7.43 (1H, dd, J = 8.8 Hz, J = 2.7 Hz,
H5), 7.38 (1H, ddd, J = 8.1 Hz, J = 2.0 Hz, J = 1.1 Hz, H60), 7.34–7.24
(2H, m, H6, H50), 6.84 (1H, tdd, J = 8.3 Hz, J = 2.6 Hz, J = 1.1 Hz,
H40), 4.32–4.13 (4H, m, CHAHB), 1.34 (6H, td, J = 7.1 Hz, J = 1.1 Hz,
CH3); 13C NMR (CDCl3, 75 MHz): d 162.97 (1C, d, J = 243.2 Hz,
C30), 161.94, 145.20 (1C, d, J = 6.9 Hz), 139.57 (1C, d, J = 10.9 Hz),
132.19 (1C, d, J = 1.8 Hz), 131.73 (1C, d, J = 2.0 Hz), 131.54 (1C, d,
J = 1.1 Hz), 130.07 (1C, d, J = 9.3 Hz), 129.41 (1C, d, J = 5.7 Hz),
122.74 (1C, d, J = 2.4 Hz), 115.18 (1C, d, J = 3.0 Hz, C60), 111.22
(1C, d, J = 21.2 Hz), 107.36 (1C, d, J = 26.3 Hz), 65.73 (2C, d,
J = 6.1 Hz, CHAHB), 16.04 (2C, d, J = 6.4 Hz, CH3). Anal. Calcd for C17-
H18ClFNO5P (401.75): C, 50.82; H, 4.52; N, 3.49. Found: C, 51.02; H,
4.57; N, 3.60.
m
;
(1H, br s, NH), 8.04 (1H, d, J = 2.6 Hz, H3), 7.72–7.61 (2H, m, H20,
H60), 7.57 (1H, dd, J = 8.8 Hz, J = 2.6 Hz, H5), 7.52–7.41 (2H, m,
H30, H50), 7.22 (1H, dd, J = 8.8 Hz, J = 1.5 Hz, H6), 4.34–4.09 (4H,
m, CHAHB), 1.34 (6H, td, J = 7.1 Hz, J = 1.2 Hz, CH3); 13C NMR (CDCl3,
75 MHz): d 161.75, 145.71 (1C, d, J = 6.9 Hz), 137.18, 135.15 (1C, d,
J = 1.7 Hz), 134.50, 131.98, 129.77 (1C, d, J = 5.5 Hz), 123.06 (1C, d,
J = 2.3 Hz), 121.39, 119.25 (1C, d, J = 1.9 Hz), 117.12, 65.75 (2C, d,
J = 6.1 Hz, CHAHB), 16.06 (2C, d, J = 6.5 Hz, CH3). Anal. Calcd for C17-
H18Br2NO5P (507.11): C, 40.26; H, 3.58; N, 2.76. Found: C, 40.05; H,
3.28; N, 2.46.
4.1.1.9. 4-Bromo-2-[(4-fluorophenyl)carbamoyl]phenyl diethyl
phosphate (1i).
1672 (amide I), 1620 (
1476 (
CC aromatic) cmꢀ1
Yield: 77%, white solid; mp 81 °C; IR (ATR):
CC aromatic), 1558 (amide II), 1509,
1H NMR (CDCl3, 500 MHz): d 9.45
m
4.1.1.13. 4-Chloro-2-[(4-fluorophenyl)carbamoyl]phenyl diethyl
m
;
phosphate (1m).
Yield: 56%, white solid; mp 74 °C; IR (ATR):
(1H, br s, NH), 8.04 (1H, dd, J = 2.6 Hz, J = 1.0 Hz, H3), 7.77–7.66
(2H, m, H20, H60), 7.57 (1H, dd, J = 8.7 Hz, J = 2.6 Hz, H5), 7.23
(1H, dd, J = 8.7 Hz, J = 1.4 Hz, H6), 7.10–7.00 (2H, m, H30, H50),
4.31–4.11 (4H, m, CHAHB), 1.34 (6H, td, J = 7.1 Hz, J = 1.1 Hz,
1673 (amide I), 1622 (
m
CC aromatic), 1561 (amide II), 1509, 1479
(m
CC aromatic) cmꢀ1
;
1H NMR (CDCl3, 300 MHz): d 9.48 (1H, br s,
NH), 7.90 (1H, dd, J = 2.7 Hz, J = 1.0 Hz, H3), 7.77–7.66 (2H, m, H20,
H60), 7.42 (1H, dd, J = 8.7 Hz, J = 2.7 Hz, H5), 7.28 (1H, dd, J = 8.7 Hz,
J = 1.3 Hz, H6), 7.10–6.99 (2H, m, H30, H50), 4.31–4.12 (4H, m, CHA-
HB), 1.33 (6H, td, J = 7.1 Hz, J = 1.1 Hz, CH3); 13C NMR (CDCl3,
75 MHz): d 161.75, 159.43 (1C, d, J = 242.4 Hz, C40), 145.20 (1C, d,
J = 7.0 Hz), 134.15 (1C, d, J = 2.9 Hz, C10), 132.05 (1C, d, J = 1.8 Hz),
131.70 (1C, d, J = 1.9 Hz), 131.50 (1C, d, J = 1.1 Hz), 129.54 (1C, d,
J = 5.6 Hz), 122.69 (1C, d, J = 2.4 Hz), 121.52 (2C, d, J = 7.8 Hz, C20,
C60), 115.65 (2C, d, J = 22.3 Hz, C30, C50), 65.69 (2C, d, J = 6.0 Hz,
CHAHB), 16.04 (2C, d, J = 6.4 Hz, CH3). Anal. Calcd for C17H18ClFNO5-
CH3); 13C NMR (CDCl3, 125 MHz):
d 161.60, 159.42 (1C, d,
J = 242.4 Hz, C40), 145.77 (1C, d, J = 7.0 Hz), 135.02 (1C, d,
J = 1.7 Hz), 134.45, 134.14 (1C, d, J = 2.7 Hz, C10), 129.80 (1C, d,
J = 5.8 Hz), 122.99 (1C, d, J = 2.2 Hz), 121.51 (2C, d, J = 7.7 Hz, C20,
C60), 119.17 (1C, d, J = 2.0 Hz), 115.63 (2C, d, J = 22.3 Hz, C30, C50),
65.68 (2C, d, J = 6.0 Hz, CHAHB), 16.03 (2C, d, J = 6.4 Hz, CH3). Anal.
Calcd for C17H18BrFNO5P (446.20): C, 45.76; H, 4.07; N, 3.14.
Found: C, 45.45; H, 3.88; N, 2.97.