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4.3.63. 2-(4-Cyanophenyl)-5-hydroxyisoindole-1,3-dione (21n)
This compound was prepared by a similar method to that used
for the synthesis of 8, starting from 4-aminobenzonitrile. Pale yel-
low solid (92%); 1H NMR (DMSO-d6, 500 MHz) d 11.10 (s, 1H), 8.00
(d, J = 9.1 Hz, 2H), 7.82 (d, J = 7.9 Hz, 1H), 7.67 (d, J = 9.1 Hz, 2H),
7.24 (d, J = 2.4 Hz, 1H), 7.20 (dd, J = 7.9, 2.4 Hz, 1H); MS (FAB) m/z
265 (M+H)+.
(m, 2H), 7.46–7.43 (m, 3H), 7.18 (d, J = 16.5 Hz, 1H); mp 207.5–
209 °C; MS (FAB) m/z 415 (M+H)+.
4.3.70. 2-(2-Methoxyphenyl)isoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22f)
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21f. White solid (78%); 1H
NMR (DMSO-d6, 500 MHz) d 8.30 (d, J = 9.1 Hz, 2H), 8.14 (d,
J = 9.1 Hz, 2H), 8.06 (d, J = 15.9 Hz, 1H), 8.06 (d, J = 7.9 Hz, 1H),
7.92 (d, J = 1.8 Hz, 1H), 7.77 (dd, J = 7.9, 1.8 Hz, 1H), 7.49 (ddd,
J = 7.9, 7.9, 1.8 Hz, 1H), 7.38 (dd, J = 7.9, 1.8 Hz, 1H), 7.22 (dd,
J = 7.9, 1.8 Hz, 1H), 7.18 (d, J = 15.9 Hz, 1H), 7.09 (ddd, J = 7.9, 7.9,
1.8 Hz, 1H), 3.75 (s, 3H); mp 204–204.5 °C; MS (FAB) m/z 445
(M+H)+.
4.3.64. 5-Hydroxy-2-(4-nitrophenyl)isoindole-1,3-dione (21o)
This compound was prepared by a similar method to that used
for the synthesis of 8, starting from 4-nitroaniline. Yellow solid
(74%); 1H NMR (DMSO-d6, 500 MHz) d 11.02 (s, 1H), 8.38 (d
J = 8.5 Hz, 2H), 7.84 (d, J = 7.9 Hz, 1H), 7.76 (d J = 8.5 Hz, 2H), 7.25
(d, J = 1.8 Hz, 1H), 7.21 (dd, J = 7.9, 1.8 Hz, 1H).
4.3.65. 2-(1-Propyl)isoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22a)
4.3.71. 2-(3-Methoxyphenyl)isoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22g)
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21a. White solid (79%); 1H
NMR (DMSO-d6, 500 MHz) d 8.29 (d, J = 9.1 Hz, 2H), 8.13 (d,
J = 9.1 Hz, 2H), 8.04 (d, J = 15.9 Hz, 1H), 7.95 (d, J = 7.9 Hz, 1H),
7.80 (d, J = 1.8 Hz, 1H), 7.68 (dd, J = 7.9, 1.8 Hz, 1H), 7.15 (d,
J = 15.9 Hz, 1H), 3.53 (t, J = 7.3 Hz, 2H), 1.60 (qt, J = 7.3, 7.3 Hz,
2H), 0.87 (t, J = 7.3 Hz, 3H); mp 149–151 °C; MS (FAB) m/z 381
(M+H)+.
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21g. White solid (74%); 1H
NMR (DMSO-d6, 500 MHz) d 8.30 (d, J = 9.1 Hz, 2H), 8.13 (d,
J = 9.1 Hz, 2H), 8.06 (d, J = 15.9 Hz, 1H), 8.05 (d, J = 7.9 Hz, 1H),
7.91 (d, J = 1.8 Hz, 1H), 7.75 (dd, J = 7.9, 1.8 Hz, 1H), 7.43 (dd,
J = 7.9, 7.9 Hz, 1H), 7.18 (d, J = 15.9 Hz, 1H), 7.07–7.02 (m, 3H),
3.78 (s, 3H); MS (FAB) m/z 445 (M+H)+.
4.3.72. 2-(4-Methoxyphenyl)isoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22h)
4.3.66. 2-Isopropylisoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22b)
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21h. White solid (74%); 1H
NMR (DMSO-d6, 500 MHz) d 8.32 (d, J = 8.5 Hz, 2H), 8.01 (d,
J = 7.9 Hz, 1H), 7.96 (d, J = 15.9 Hz, 1H), 7.79 (d, J = 1.8 Hz, 1H),
7.78 (d, J = 8.5 Hz, 2H), 7.58 (dd, J = 7.9, 1.8 Hz, 1H), 7.34 (d,
J = 8.5 Hz, 2H), 7.03 (d, J = 8.5 Hz, 2H), 6.79 (d, J = 15.9 Hz, 1H),
3.86 (s, 3H); mp 206–208 °C; MS (FAB) m/z 445 (M+H)+.
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21b. White solid (95%); 1H
NMR (CDCl3, 500 MHz)
d 8.31 (d, J = 9.1 Hz, 2H), 7.94 (d,
J = 15.9 Hz, 1H), 7.87 (d, J = 7.9 Hz, 1H), 7.77 (d, J = 9.1 Hz, 2H),
7.65 (d, J = 1.8 Hz, 1H), 7.48 (dd, J = 7.9, 1.8 Hz, 1H), 6.77 (d,
J = 15.9 Hz, 1H), 4.54 (sept, J = 6.7 Hz, 2H), 1.50 (d, J = 6.7 Hz, 6H);
mp 150–152 °C; MS (FAB) m/z 381 (M+H)+.
4.3.73. 2-(4-Methylphenyl)isoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22i)
4.3.67. 2-(1-Hexyl)isoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22c)
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21i. White solid (74%); 1H
NMR (DMSO-d6, 500 MHz) d 8.32 (d, J = 8.5 Hz, 2H), 8.01 (d,
J = 7.9 Hz, 1H), 7.96 (d, J = 15.9 Hz, 1H), 7.79 (d, J = 1.8 Hz, 1H),
7.78 (d, J = 8.5 Hz, 2H), 7.58 (dd, J = 7.9, 1.8 Hz, 1H), 7.34 (d,
J = 8.5 Hz, 2H), 7.03 (d, J = 8.5 Hz, 2H), 6.79 (d, J = 15.9 Hz, 1H),
3.86 (s, 3H); mp 207–209 °C; MS (FAB) m/z 445 (M+H)+.
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21c. White solid (65%); 1H
NMR (CDCl3, 500 MHz)
d 8.31 (d, J = 8.5 Hz, 2H), 7.95 (d,
J = 15.9 Hz, 1H), 7.90 (d, J = 7.9 Hz, 1H), 7.77 (d, J = 8.5 Hz, 2H),
7.68 (d, J = 1.8 Hz, 1H), 7.50 (dd, J = 7.9, 1.8 Hz, 1H), 6.77 (d,
J = 15.9 Hz, 1H), 3.69 (t, J = 7.3 Hz, 2H), 1.69–1.64 (m, 2H), 1.36–
1.29 (m, 6H), 0.88 (t, J = 7.0 Hz, 3H); mp 127–132 °C; MS (FAB)
m/z 423 (M+H)+.
4.3.74. 2-(4-Isopropylphenyl)isoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22j)
4.3.68. 2-Cyclohexylisoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22d)
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21j. Pale yellow crystals
(76%); 1H NMR (DMSO-d6, 500 MHz) d 8.30 (d, J = 9.1 Hz, 2H),
8.14 (d, J = 9.1 Hz, 2H), 8.06 (d, J = 15.9 Hz, 1H), 8.05 (d, J = 7.9 Hz,
1H), 7.90 (d, J = 1.8 Hz, 1H), 7.75 (dd, J = 7.9, 1.8 Hz, 1H), 7.40 (d,
J = 8.5 Hz, 2H), 7.35 (d, J = 8.5 Hz, 2H), 7.18 (d, J = 15.9 Hz, 1H),
2.96 (sept, J = 6.7 Hz, 1H), 1.32 (d, J = 6.7 Hz, 6H); mp 187–
188 °C; MS (FAB) m/z 457 (M+H)+.
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21d. White solid (92%); 1H
NMR (CDCl3, 500 MHz)
d 8.31 (d, J = 9.1 Hz, 2H), 7.94 (d,
J = 15.9 Hz, 1H), 7.87 (d, J = 7.9 Hz, 1H), 7.77 (d, J = 9.1 Hz, 2H),
7.65 (d, J = 1.8 Hz, 1H), 7.48 (dd, J = 7.9, 1.8 Hz, 1H), 6.77 (d,
J = 15.9 Hz, 1H), 4.14–4.09 (m, 1H), 2.25–2.17 (m, 2H), 1.90–1.86
(m, 2H), 1.76–1.69 (m, 2H), 1.41–1.26 (m, 4H); mp 177.5–179 °C;
MS (FAB) m/z 421 (M+H)+.
4.3.75. 2-(4-tert-Butylphenyl)isoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22k)
4.3.69. 2-Phenylisoindole-1,3-dione-5-yl (E)-3-(4-
nitrophenyl)acrylate (22e)
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21k. Pale yellow crystals
(80%); 1H NMR (DMSO-d6, 500 MHz) d 8.30 (d, J = 8.5 Hz, 2H),
8.14 (d, J = 8.5 Hz, 2H), 8.06 (d, J = 16.4 Hz, 1H), 8.05 (d, J = 7.9 Hz,
1H), 7.90 (d, J = 1.8 Hz, 1H), 7.75 (dd, J = 7.9, 1.8 Hz, 1H), 7.54 (d,
J = 8.5 Hz, 2H), 7.37 (d, J = 8.5 Hz, 2H), 7.18 (d, J = 16.4 Hz, 1H),
1.32 (s, 9H); mp 209–210 °C; MS (FAB) m/z 471 (M+H)+.
This compound was prepared by a similar method to that used
for the synthesis of 9g, starting from 21e. White solid (60%); 1H
NMR (DMSO-d6, 500 MHz) d 8.30 (d, J = 9.1 Hz, 2H), 8.13 (d,
J = 9.1 Hz, 2H), 8.06 (d, J = 8.5 Hz, 1H), 8.05 (d, J = 16.5 Hz, 1H),
7.92 (d, J = 1.8 Hz, 1H), 7.76 (dd, J = 8.5, 1.8 Hz, 1H), 7.55–7.52