8
Synthesis, Characterization and Evaluation of in vitro Antitumor Activities
J. Braz. Chem. Soc.
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3
1
1
1
33.5, 133.7, 135.1, 137.0, 138.4, 139.5, 140.2, 148.8,
81.7; IR (ATR) ν / cm 1677 (m), 1606 (m), 1478 (w),
349 (s), 1301 (m), 1240 (m); HRMS calculated for
1H), 8.28-8.31 (m, 2H); C NMR (125.76 MHz, CDCl )
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-1
d 60.7, 124.4, 124.8, 127.4, 127.8, 128.1, 128.2, 128.6,
129.3, 130.0, 130.1, 130.5, 130.6, 133.6, 134.4, 134.9,
135.0, 136.2, 136.4, 137.1, 139.1, 139.8, 148.3, 182.2; IR
C H BrN O S 575.0276, found 575.0102.
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8
20
2
5
-1
(
ATR) ν / cm 1677 (m), 1596 (m), 1471 (m), 1343 (s),
(E)-3-(4-Chlorobenzylidene)-2-(3-nitrophenyl)-2,3-dihydro-
1295 (m), 1239 (m); HRMS calculated for C H BrN O S
28
20
2
5
1
-(phenylsulfonyl)-quinolin-4(1H)-one (33)
575.0276, found 575.0035.
Pale yellow amorphous solid, yield 73.1%, purity of
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9
9.1%, mp 207-210 °C; H NMR (500.13 MHz, CDCl )
(E)-3-(4-Bromobenzylidene)-2-(2-bromophenyl)-
2,3-dihydro-1-(phenylsulfonyl)-quinolin-4(1H)-one (36)
3
d 6.72 (s, 1H), 7.10-7.13 (m, 2H), 7.13-7.16 (m, 2H),
.21-7.25 (m, 2H), 7.32 (dt, J 1.05, 7.59 Hz, 1H), 7.41-7.43
m, 2H), 7.49-7.54 (m, 2H), 7.57 (ddd, J 1.66, 7.41,
7
(
Pale yellow crystalline solid, yield 55.6%, purity of
1
98.6%, mp 219-221 °C; H NMR (500.13 MHz, CDCl )
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7
7
.11 Hz, 1H), 7.65 (s, 1H), 7.76 (dd, J 0.63, 8.18 Hz, 1H),
.81 (tdd, J 0.95, 1.90, 7.85 Hz, 1H), 7.89 (dd, J 1.60,
.85 Hz, 1H), 8.11-8.14 (m, 1H), 8.24 (t, J 2.53 Hz, 1H);
d 6.74 (dd, J 1.48, 7.83 Hz, 1H), 6.91 (s, 1H), 6.98 (dt,
J 1.23, 7.61 Hz, 1H), 7.03-7.06 (m, 2H), 7.09-7.13 (m, 3H),
7.22-7.26 (m, 2H), 7.34 (ddd, J 3.55, 5.05, 7.75 Hz, 1H),
7.49-7.53 (m, 3H), 7.56 (s, 1H), 7.56-7.59 (m, 2H), 7.70
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C NMR (125.76 MHz, CDCl ) d 59.3, 122.4, 123.8, 127.3,
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13
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1
1
1
27.8, 128.1, 128.2, 128.3, 129.1, 129.7, 129.7, 130.2,
31.2, 131.7, 133.5, 133.6, 135.1, 137.0, 137.1, 138.4,
(dd, J 1.23, 7.98 Hz, 1H), 7.86-7.89 (m, 1H); C NMR
(125.76 MHz, CDCl ) d 60.9, 124.8, 125.1, 127.2, 127.6,
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39.5, 140.1, 148.8, 181.7; IR (ATR) ν / cm 1674 (m),
605 (m), 1478 (w), 1348 (s), 1302 (m), 1238 (m); HRMS
128.0, 128.1, 128.5, 129.3, 130.2, 130.3, 130.3, 131.4,
131.5, 132.5, 132.6, 133.5, 134.7, 134.8, 136.4, 136.4,
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calculated for C H ClN O S 531.0781, found 531.0619.
139.0, 139.1, 182.6; IR (ATR) ν / cm 1675 (m), 1605 (m),
474 (w), 1351 (s), 1292 (m), 1239 (m); HRMS calculated
for C H Br NO S 607.9531, found 607.9454.
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20
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5
1
(E)-3-(3-Nitrobenzylidene)-2-(2-bromophenyl)-2,3-dihydro-
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20
2
3
1
-(phenylsulfonyl)-quinolin-4(1H)-one (34)
Pale yellow to white amorphous solid, yield 79.4%,
(E)-3-(4-Chlorobenzylidene)-2-(2-bromophenyl)-
2,3-dihydro-1-(phenylsulfonyl)-quinolin-4(1H)-one (37)
1
purity of 98.5%; H NMR (500.13 MHz, CDCl ) d 6.74 (dd,
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J 1.53, 7.83 Hz, 1H), 6.86 (s, 1H), 7.01 (dt, J 1.32, 7.63 Hz,
Pale yellow crystalline solid, yield 47.1%, purity of
1
1H), 7.11-7.14 (m, 2H), 7.14 (ddd, J 1.60, 7.43, 7.83 Hz,
1H), 7.27-7.31 (m, 2H), 7.38 (ddd, J 1.51, 7.06, 7.76 Hz,
1H), 7.44 (tdd, J 0.85, 1.70, 7.70 Hz, 1H), 7.51 (ddd, J 0.45,
1.50, 8.05 Hz, 1H), 7.53-7.58 (m, 2H), 7.63 (t, J 7.98 Hz,
2H), 7.66 (s, 1H), 7.74 (dd, J 1.28, 7.98 Hz, 1H), 7.91 (ddd,
98.8%, mp 204-205 °C; H NMR (500.13 MHz, CDCl )
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d 6.75 (dd, J 1.75, 7.85 Hz, 1H), 6.91 (s, 1H), 6.98 (dt,
J 1.48, 7.60 Hz, 1H), 7.09-7.13 (m, 5H), 7.22-7.26 (m, 2H),
7.34 (ddd, J 3.35, 5.23, 7.75 Hz, 1H), 7.40-7.43 (m, 2H),
7.49-7.53 (m, 3H), 7.59 (s, 1H), 7.70 (dd, J 1.38, 7.98 Hz,
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J 0.50, 1.58, 7.78 Hz, 1H), 7.99 (t, J 1.98 Hz, 1H), 8.29
1H), 7.86-7.89 (m, 1H); C NMR (125.76 MHz, CDCl )
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(
ddd, J 0.90, 2.20, 8.23 Hz, 1H); C NMR (125.76 MHz,
d 60.9, 124.8, 127.2, 127.6, 128.0, 128.1, 128.5, 129.3,
129.6, 130.2, 130.3, 130.3, 131.3, 131.4, 132.0, 133.5,
134.7, 134.8, 136.4, 136.7, 139.0, 139.1, 182.6; IR (ATR)
CDCl ) d 60.8, 124.6, 124.7, 124.9, 127.3, 127.8, 128.1,
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28.2, 128.7, 129.4, 130.1, 130.1, 130.4, 130.6, 133.7,
33.9, 134.8, 134.9, 135.0, 135.2, 136.2, 136.4, 137.1,
39.1, 148.7, 182.2; IR (ATR) ν / cm 1672 (m), 1599 (m),
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ν / cm 1676 (m), 1605 (m), 1474 (w), 1351 (s), 1293
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(m), 1239 (m); HRMS calculated for C H BrClNO SNa
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471 (m), 1351 (s), 1294 (m), 1242 (m); HRMS calculated
585.9855, found 585.9566.
for C H BrN O S 575.0276, found 575.0015.
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(E)-3-(3-Nitrobenzylidene)-2-(2-chlorophenyl)-2,3-dihydro-
(E)-3-(4-Nitrobenzylidene)-2-(2-bromophenyl)-2,3-dihydro-
1-(phenylsulfonyl)-quinolin-4(1H)-one (38)
1
-(phenylsulfonyl)-quinolin-4(1H)-one (35)
Pale yellow to white amorphous solid, yield 81.7%,
purity of 98.9%, mp 224-226 °C; H NMR (500.13 MHz,
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Pale yellow crystalline solid, yield 69.7%, purity of
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9.7%, mp 207-209 °C; H NMR (500.13 MHz, CDCl )
CDCl ) d 6.76 (dd, J 1.68, 7.83 Hz, 1H), 6.91 (s, 1H),
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d 6.74 (dd, J 1.58, 7.88 Hz, 1H), 6.90 (s, 1H), 7.01 (dt,
J 1.30, 7.60 Hz, 1H), 7.11-7.14 (m, 2H), 7.14 (dt, J 1.63,
6.98 (dt, J 1.40, 7.65 Hz, 1H), 7.12-7.14 (m, 2H), 7.24 (dt,
J 1.52, 7.75 Hz, 1H), 7.28-7.32 (m, 2H), 7.38 (ddd, J 1.76,
6.76, 7.76 Hz, 1H), 7.42 (tdd, J 0.85, 1.70, 7.70 Hz, 1H),
7.51-7.58 (m, 4H), 7.63 (t, J 8.08 Hz, 1H), 7.64 (s, 1H),
7.93 (dd, J 1.40, 7.70 Hz, 1H), 7.97 (t, J 2.00 Hz, 1H), 8.29
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.73 Hz, 1H), 7.25-7.29 (m, 2H), 7.31-7.34 (m, 2H), 7.37
ddd, J 1.51, 7.06, 7.74 Hz, 1H), 7.51 (ddd, J 0.55, 1.53,
.08 Hz, 1H), 7.52-7.56 (m, 2H), 7.66 (s, 1H), 7.72 (dd,
J 1.33, 7.98 Hz, 1H), 7.90 (ddd, J 0.51, 1.59, 7.76 Hz,
(
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(ddd, J 0.94, 2.19, 8.14 Hz, 1H); C NMR (125.76 MHz,