J. Wu et al. / European Journal of Medicinal Chemistry 80 (2014) 340e351
349
chromatography (SiO2, petroether/ethyl acetate) to afford target
CDCl3): d 171.33, 166.51, 154.75, 139.72, 138.04, 134.56, 130.72,
compounds 32e44.
129.99, 129.64, 128.71, 127.92, 127.60, 127.41, 126.53, 125.19, 120.86,
112.12, 64.25, 55.69, 44.06, 33.07. HR MS (ESI) calcd for
[C24H22N2O3S þ Na]þ 441.1243, found 441.1255.
5.4.2. 2-(3-N,N-diethylamino carbonylphenyl)-3-(2-
methoxyphenyl)-4-thiazolidinone (32)
Reaction of 31 and diethylamine and then purification to give
the target compound 32. Yield: 32%; 1H NMR (300 MHz, CDCl3)
d
5.4.7. 2-(3-(phenylethyl amino carbonyl)phenyl)-3-(2-
methoxyphenyl)-4-thiazolidinone (37)
7.40 (d, J ¼ 8.7 Hz, 1H), 7.32e7.27 (m, 3H), 7.19 (dd, J ¼ 7.8, 7.8 Hz,
The title compound was synthesized according to the procedure
of preparing 32 except using 2-phenyl ethylamine instead of
1H), 6.87 (dd, J ¼ 7.5, 8.1 Hz, 2H), 6.78 (dd, J ¼ 7.2, 7.5 Hz,1H), 6.10 (s,
1H), 3.98e3.87 (m, 2H), 3.83 (s, 3H), 3.50 (br s, 2H), 3.08 (br s, 2H),
diethylamine. Yield: 64%. 1H NMR (300 MHz, CDCl3)
d 7.66 (br s,
1.21 (br s, 3H), 1.00 (br s, 3H). 13C NMR (125 MHz, CDCl3):
d 171.28,
1H), 7.52 (d, J ¼ 7.5 Hz, 1H), 7.46 (dd, J ¼ 0.6, 7.2 Hz, 1H), 7.36e7.28
(m, 4H), 7.24e7.15 (m, 3H), 6.86 (ddd, J ¼ 1.5, 7.8, 8.4 Hz, 2H), 6.78
(dd, J ¼ 7.5, 7.8 Hz,1H), 6.11 (s,1H), 6.05 (t, J ¼ 5.1 Hz,1H), 3.98e3.86
(m, 2H), 3.80 (s, 3H), 3.69 (q, J ¼ 6.3 Hz, 2H), 2.92 (t, J ¼ 6.9 Hz, 2H).
170.46, 154.81, 139.36, 137.36, 130.21, 129.59, 129.62, 128.58, 126.91,
126.02, 125.21, 120.77, 111.96, 64.31, 55.66, 33.11, 30.89, 29.65. HR
MS (ESI) calcd for [C21H24N2O3S þ Na]þ 407.1400, found 407.1403.
13C NMR (125 MHz, CDCl3):
d 171.31, 166.68, 154.73, 139.74, 138.80,
5.4.3. 2-(3-N,N-diallylamino carbonylphenyl)-3-(2-
methoxyphenyl)-4-thiazolidinone (33)
134.85, 130.65, 130.07, 129.63, 128.75, 128.67, 127.19, 126.57, 126.48,
125.14, 120.83, 112.04, 64.23, 55.66, 41.11, 35.55, 33.07. HR MS (ESI)
calcd for [C25H24N2O3S þ Na]þ 455.1400, found 455.1402.
The title compound was synthesized according to the procedure
of preparing 32 except using diallylamine instead of diethylamine.
Yield: 66%; 1H NMR (300 MHz, CDCl3)
d 7.42e7.39 (m, 1H), 7.36 (s,
1H), 7.31e7.26 (m, 2H), 7.18 (dd, J ¼ 7.5, 8.1 Hz, 1H), 6.89e6.85 (m,
2H), 6.78 (dd, J ¼ 7.5, 7.5 Hz,1H), 6.09 (s, 1H), 5.85 (br s, 1H), 5.63 (br
s, 1H), 5.24e5.09 (m, 4H), 4.20e4.00 (m, 2H), 3.92 (dd, J ¼ 1.2,
3.6 Hz, 2H), 3.83 (s, 3H), 3.65 (br s, 2H). 13C NMR (125 MHz, CDCl3):
5.4.8. 2-(3-(phenylpropyl amino carbonyl)phenyl)-3-(2-
methoxyphenyl)-4-thiazolidinone (38)
The title compound was synthesized according to the procedure
of preparing 32 except using 3-phenyl propylamine instead of
d
171.24, 170.93, 154.79, 139.40, 136.34, 132.98, 132.58, 130.21,
diethylamine. Yield: 90%. 1H NMR (300 MHz, CDCl3)
d 7.64 (br s,
129.63, 129.09, 128.61, 127.29, 126.21, 117.64, 111.98, 64.25, 55.67,
33.09, 29.64. HR MS (ESI) calcd for [C23H24N2O3S þ Na]þ 431.1400,
found 431.1408.
1H), 7.49 (dd, J ¼ 1.5, 7.8 Hz, 2H), 7.33e7.27 (m, 3H), 7.21e7.15 (m,
4H), 6.90 (dd, J ¼ 1.5, 7.5 Hz, 1H), 6.86 (d, J ¼ 8.4 Hz, 1H), 6.78 (dd,
J ¼ 7.5, 7.8 Hz, 1H), 6.12 (s, 1H), 6.08 (t, J ¼ 5.4 Hz, 1H), 3.99e3.87 (m,
2H), 3.82 (s, 3H), 3.46 (q, J ¼ 6.6 Hz, 2H), 2.71 (t, J ¼ 7.5 Hz, 2H),
5.4.4. 2-(3-(1-piperidinyl)carbonylphenyl)-3-(2-methoxyphenyl)-
4-thiazolidinone (34)
1.99e1.89 (m, 2H). 13C NMR (125 MHz, CDCl3):
d 171.43, 166.67,
154.78, 141.37, 139.76, 134.82, 128.67, 128.53, 128.34, 127.16, 126.48,
126.06, 120.86, 112.08, 64.29, 55.71, 39.84, 33.46, 33.11, 30.98. HR
MS (ESI) calcd for [C26H26N2O3S þ Na]þ 469.1556, found 469.1554.
The title compound was synthesized according to the procedure
of preparing 32 except using piperidine instead of diethylamine.
Yield: 50%. 1H NMR (300 MHz, CDCl3)
d
7.41 (d, J ¼ 7.2 Hz,1H), 7.33e
7.27 (m, 3H), 7.18 (ddd, J ¼ 1.5, 8.4, 8.7 Hz, 1H), 6.89e6.85 (m, 2H),
6.78 (dd, J ¼ 7.2, 7.8 Hz, 1H), 6.11 (s, 1H), 3.97e3.91 (m, 2H), 3.83 (s,
5.4.9. 2-(3-(4-bromophenylethyl amino carbonyl) phenyl)-3-(2-
methoxyphenyl)-4-thiazolidinone (39)
3H), 3.67 (br s, 2H), 3.12 (br s, 2H), 1.66 (br s, 4H), 1.44 (br s, 2H). 13
C
NMR (125 MHz, CDCl3):
d 171.25, 169.46, 154.79, 139.26, 136.62,
The title compound was synthesized according to the procedure
of preparing 32 except using 4-bromophenyl ethylamine instead of
130.26, 129.56, 128.82, 128.67, 127.46, 126.41, 125.17, 120.71, 111.93,
64.28, 55.65, 33.09, 24.47. HR MS (ESI) calcd for
[C22H24N2O3S þ Na]þ 419.1400, found 419.1401.
diethylamine. Yield: 88%. 1H NMR (300 MHz, CDCl3):
d 7.67 (s, 1H),
7.54e7.47 (m, 2H), 7.45 (d, J ¼ 8.1 Hz, 2H), 7.33 (dd, J ¼ 7.8, 7.8 Hz,
1H), 7.20 (ddd, J ¼ 1.8, 8.1, 9.0 Hz, 1H), 7.10 (d, J ¼ 8.1 Hz, 2H), 6.87
(ddd, J ¼ 1.2, 7.5, 8.1 Hz, 2H), 6.79 (dd, J ¼ 7.5, 7.8 Hz, 1H), 6.12 (s,
1H), 6.05 (t, J ¼ 5.1 Hz, 1H), 3.99e3.88 (m, 2H), 3.81 (s, 3H), 3.66 (q,
J ¼ 6.6 Hz, 2H), 2.88 (t, J ¼ 6.9 Hz, 2H). 13C NMR (125 MHz, CDCl3):
5.4.5. 2-(3-(phenyl amino carbonyl)phenyl)-3-(2-methoxyphenyl)-
4-thiazolidinone (35)
The title compound was synthesized according to the procedure
of preparing 32 except using aniline instead of diethylamine. Yield:
d
171.34, 166.75, 154.80, 139.91, 137.78, 134.72, 131.76, 130.83,
70%. 1H NMR (300 MHz, CDCl3)
d 7.96 (s, 1H), 7.85 (s, 1H), 7.72 (d,
130.52, 130.09, 129.69, 128.79, 127.15, 126.49, 125.21, 120.90, 120.47,
112.12, 64.26, 55.73, 41.00, 35.04, 33.11. HR MS (ESI) calcd for
[C25H23BrN2O3S þ Na]þ 533.0505, found 533.0504.
J ¼ 7.5 Hz, 1H), 7.59 (d, J ¼ 7.5 Hz, 1H), 7.52 (d, J ¼ 7.2 Hz, 1H), 7.39e
7.33 (m, 3H), 7.21e7.12 (m, 2H), 6.91 (dd, J ¼ 1.2, 7.8 Hz, 1H), 6.85 (d,
J ¼ 8.1 Hz, 1H), 6.78 (dd, J ¼ 7.2, 7.2 Hz, 1H), 6.17 (s, 1H), 3.99e3.86
(m, 2H), 3.81 (s, 3H). 13C NMR (125 MHz, CDCl3):
d 171.46, 165.01,
154.75, 139.80, 137.84, 135.20, 131.03, 130.05, 129.74, 128.96, 128.82,
127.59, 126.75, 125.09, 124.54, 120.88, 120.30, 112.11, 64.31, 55.73,
33.13. HR MS (ESI) calcd for [C23H20N2O3S þ Na]þ 427.1087, found
427.14096.
5.4.10. 2-(3-(2-bromophenylethyl amino carbonyl) phenyl)-3-(2-
methoxyphenyl)-4-thiazolidinone (40)
The title compound was synthesized according to the procedure
of preparing 32 except using 2-bromophenyl ethylamine instead of
diethylamine. Yield: 86%. 1H NMR (300 MHz, CDCl3):
d 8.01 (s, 1H),
5.4.6. 2-(3-(benzyl amino carbonyl)phenyl)-3-(2-methoxyphenyl)-
4-thiazolidinone (36)
7.70 (br s, 1H), 7.58 (d, J ¼ 7.8 Hz, 2H), 7.47 (d, J ¼ 8.1 Hz, 1H), 7.32
(dd, J ¼ 7.5, 7.8 Hz, 1H), 7.26 (br s, 1H), 7.21e7.11 (m, 2H), 6.88e6.84
(m, 2H), 6.78 (dd, J ¼ 7.2, 7.5 Hz, 1H), 6.17 (t, J ¼ 5.1 Hz, 1H), 6.12 (s,
1H), 4.00e3.88 (m, 2H), 3.81 (s, 3H), 3.71 (q, J ¼ 6.6 Hz, 2H), 3.09 (t,
The title compound was synthesized according to the procedure
of preparing 32 except using benzyl amine instead of diethylamine.
Yield: 51%. 1H NMR (300 MHz, CDCl3)
d
7.76 (s, 1H), 7.64 (d,
J ¼ 6.9 Hz, 2H). 13C NMR (125 MHz, CDCl3):
d 171.32, 166.83, 154.77,
J ¼ 7.2 Hz, 1H), 7.49 (d, J ¼ 7.5 Hz, 1H), 7.39e7.32 (m, 5H), 7.16 (ddd,
J ¼ 0.6, 7.5, 7.5 Hz, 1H), 6.89 (d, J ¼ 7.5 Hz, 1H), 6.83 (d, J ¼ 8.1 Hz,
1H), 6.77 (dd, J ¼ 7.5, 7.8 Hz, 1H), 6.47 (br s, 1H), 6.13 (s, 1H), 4.59 (d,
J ¼ 5.7 Hz, 2H), 3.96e3.83 (m, 2H), 3.78 (s, 3H). 13C NMR (125 MHz,
139.75, 138.27, 134.77, 132.95, 131.03, 130.70, 130.09, 129.65, 128.69,
128.38, 127.69, 127.30, 126.49, 125.17, 124.54, 120.85, 112.08, 64.27,
55.70, 39.89, 35.55, 33.10. HR MS (ESI) calcd for
[C25H23BrN2O3S þ Na]þ 533.0505, found 533.0504.