Chem. J. Chinese Universities ›› 2016, Vol. 37 ›› Issue (6): 1093.doi: 10.7503/cjcu20160103
• Organic Chemistry • Previous Articles Next Articles
GUO Liang1,2, CAO Rihui3,*(), FAN Wenxi2, GAN Ziyun2, MA Qin2
Received:
2016-02-19
Online:
2016-06-10
Published:
2016-05-18
Contact:
CAO Rihui
E-mail:caorihui@sysn.edu.cn
CLC Number:
TrendMD:
GUO Liang, CAO Rihui, FAN Wenxi, GAN Ziyun, MA Qin. Design, Synthesis and in vitro Antitumor Activities of Novel Bivalent β-Carbolines†[J]. Chem. J. Chinese Universities, 2016, 37(6): 1093.
Compd. | m.p./℃ | Compd. | m.p./℃ |
---|---|---|---|
2a | 121.3—121.9(121—123[ | 3a | >270 |
2b | 98.7—99.2(99—101[ | 3b | 257.1—258.9(258—260[ |
2c | 104.2—104.8(104—105[ | 3c | 205.3—206.7(205—206[ |
2d | 80.3—80.6 | 3d | 230.9—231.6 |
2e | 65.4—65.7 | 3e | 214.2—216.4 |
2f | 111.7—112.6(112—113[ | 3f | 246.2—247.9(247—248[ |
2g | 117.5—118.6(117—118[ | 3g | 258.3—259.6(258—259[ |
Table 1 Melting points for compounds 2a—2g and 3a—3g
Compd. | m.p./℃ | Compd. | m.p./℃ |
---|---|---|---|
2a | 121.3—121.9(121—123[ | 3a | >270 |
2b | 98.7—99.2(99—101[ | 3b | 257.1—258.9(258—260[ |
2c | 104.2—104.8(104—105[ | 3c | 205.3—206.7(205—206[ |
2d | 80.3—80.6 | 3d | 230.9—231.6 |
2e | 65.4—65.7 | 3e | 214.2—216.4 |
2f | 111.7—112.6(112—113[ | 3f | 246.2—247.9(247—248[ |
2g | 117.5—118.6(117—118[ | 3g | 258.3—259.6(258—259[ |
Compd. | 1H NMR(400 MHz, CDCl3), δ | FAB-MS,m/z [M+1]+ |
---|---|---|
2d | 8.30(d, J=5.2 Hz, 1H), 7.98(dd, J=8.8, 3.6 Hz, 1H), 7.74(d, J=5.2 Hz, 1H), 6.85—6.91(m, 2H), 4.44(t, J=8.0 Hz, 2H), 3.96(s, 3H), 3.03(s, 3H), 1.79—1.87(m, 2H), 1.40—1.49(m, 2H), 1.27—1.39(m, 4H), 0.91(t, J=7.2 Hz, 3H) | 297 |
2e | 8.30(d, J=5.2 Hz, 1H), 8.01(dd, J=8.8, 3.2 Hz, 1H), 7.77(d, J=5.2 Hz, 1H), 6.83—6.94(m, 2H), 4.46(t, J=8.0 Hz, 2H), 3.95(s, 3H), 3.06(s, 3H), 1.75—1.91(m, 2H), 1.18—1.48(m, 10H), 0.88(t, J=7.2 Hz, 3H) | 325 |
3a | 8.32(d, J=5.2 Hz, 1H); 8.07(d, J=8.8 Hz, 1H), 7.86(d, J=5.2 Hz, 1H), 7.03—7.12(m, 2H), 4.11(s, 3H), 2.96(s, 3H) | 213 |
3d | 8.30(d, J=5.2 Hz, 1H); 7.98(d, J=8.4 Hz, 1H), 7.82(d, J=5.2 Hz, 1H), 7.02—7.11(m, 2H), 4.44(t, J=8.0 Hz, 2H), 2.96(s, 3H), 1.74—1.79(m, 2H), 1.28—1.37(m, 6H), 0.90(t, J=7.2 Hz, 3H) | 283 |
3e | 8.29(d, J=6.0 Hz, 1H); 8.02(d, J=8.8 Hz, 1H), 7.90(d, J=5.2 Hz, 1H), 7.02(d, J=8.8 Hz, 1H), 6.86(s, 1H), 4.48(t, J=8.0 Hz, 2H), 2.96(s, 3H), 1.68—1.83(m, 2H), 1.12—1.43(m, 10H), 0.89(t, J=6.8 Hz, 3H) | 311 |
Table 2 1H NMR data and FAB-MS data of compounds 2d, 2e, 3a, 3d and 3e
Compd. | 1H NMR(400 MHz, CDCl3), δ | FAB-MS,m/z [M+1]+ |
---|---|---|
2d | 8.30(d, J=5.2 Hz, 1H), 7.98(dd, J=8.8, 3.6 Hz, 1H), 7.74(d, J=5.2 Hz, 1H), 6.85—6.91(m, 2H), 4.44(t, J=8.0 Hz, 2H), 3.96(s, 3H), 3.03(s, 3H), 1.79—1.87(m, 2H), 1.40—1.49(m, 2H), 1.27—1.39(m, 4H), 0.91(t, J=7.2 Hz, 3H) | 297 |
2e | 8.30(d, J=5.2 Hz, 1H), 8.01(dd, J=8.8, 3.2 Hz, 1H), 7.77(d, J=5.2 Hz, 1H), 6.83—6.94(m, 2H), 4.46(t, J=8.0 Hz, 2H), 3.95(s, 3H), 3.06(s, 3H), 1.75—1.91(m, 2H), 1.18—1.48(m, 10H), 0.88(t, J=7.2 Hz, 3H) | 325 |
3a | 8.32(d, J=5.2 Hz, 1H); 8.07(d, J=8.8 Hz, 1H), 7.86(d, J=5.2 Hz, 1H), 7.03—7.12(m, 2H), 4.11(s, 3H), 2.96(s, 3H) | 213 |
3d | 8.30(d, J=5.2 Hz, 1H); 7.98(d, J=8.4 Hz, 1H), 7.82(d, J=5.2 Hz, 1H), 7.02—7.11(m, 2H), 4.44(t, J=8.0 Hz, 2H), 2.96(s, 3H), 1.74—1.79(m, 2H), 1.28—1.37(m, 6H), 0.90(t, J=7.2 Hz, 3H) | 283 |
3e | 8.29(d, J=6.0 Hz, 1H); 8.02(d, J=8.8 Hz, 1H), 7.90(d, J=5.2 Hz, 1H), 7.02(d, J=8.8 Hz, 1H), 6.86(s, 1H), 4.48(t, J=8.0 Hz, 2H), 2.96(s, 3H), 1.68—1.83(m, 2H), 1.12—1.43(m, 10H), 0.89(t, J=6.8 Hz, 3H) | 311 |
Compd. | Appearance | Yield(%) | m. p./℃ | FAB-MS, m/z [M+1]+ |
---|---|---|---|---|
4a | White solid | 45 | >270 | 465 |
4b | White solid | 45 | 131.3—132.3 | 507 |
4c | White solid | 57 | >270 | 507 |
4d | Slightly yellow solid | 64 | >270 | 549 |
4e | White solid | 48 | >270 | 577 |
4f | Yellow solid | 55 | 135.6—137.1 | 591 |
4g | Slightly yellow solid | 52 | 141.9—143.3 | 619 |
4h | Slightly yellow solid | 54 | 108.1—109.5 | 633 |
4i | Yellow solid | 42 | 137.6—138.9 | 675 |
4j | White solid | 46 | 106.3—107.6 | 661 |
4k | White solid | 44 | 107.0—108.1 | 704 |
4l | White solid | 49 | 95.2—96.6 | 746 |
4m | Slightly yellow solid | 56 | 187.9—188.1 | 563 |
4n | White solid | 62 | 123.3—124.6 | 605 |
4o | White solid | 48 | 115.8—116.9 | 647 |
4p | Yellow solid | 47 | 190.0—191.7 | 687 |
4q | White solid | 45 | >270 | 715 |
4r | White solid | 49 | 101.1—102.4 | 729 |
4s | White solid | 56 | 122.8—124.5 | 772 |
Table 3 Appearance, yield, melting point and MS data of target compounds 4a—4s
Compd. | Appearance | Yield(%) | m. p./℃ | FAB-MS, m/z [M+1]+ |
---|---|---|---|---|
4a | White solid | 45 | >270 | 465 |
4b | White solid | 45 | 131.3—132.3 | 507 |
4c | White solid | 57 | >270 | 507 |
4d | Slightly yellow solid | 64 | >270 | 549 |
4e | White solid | 48 | >270 | 577 |
4f | Yellow solid | 55 | 135.6—137.1 | 591 |
4g | Slightly yellow solid | 52 | 141.9—143.3 | 619 |
4h | Slightly yellow solid | 54 | 108.1—109.5 | 633 |
4i | Yellow solid | 42 | 137.6—138.9 | 675 |
4j | White solid | 46 | 106.3—107.6 | 661 |
4k | White solid | 44 | 107.0—108.1 | 704 |
4l | White solid | 49 | 95.2—96.6 | 746 |
4m | Slightly yellow solid | 56 | 187.9—188.1 | 563 |
4n | White solid | 62 | 123.3—124.6 | 605 |
4o | White solid | 48 | 115.8—116.9 | 647 |
4p | Yellow solid | 47 | 190.0—191.7 | 687 |
4q | White solid | 45 | >270 | 715 |
4r | White solid | 49 | 101.1—102.4 | 729 |
4s | White solid | 56 | 122.8—124.5 | 772 |
Compd. | 1H NMR(400 MHz), δa | 13C NMR(100 MHz), δb |
---|---|---|
4a | 8.27(d, J=5.2 Hz, 2H), 7.97(d, J=8.8 Hz, 2H), 7.74(d, J=5.2 Hz, 2H), 6.89—6.94(m, 4H), 4.36(t, J=6.0 Hz, 4H), 4.07(s, 6H), 3.07(s, 6H), 2.42—2.45(m, 2H) | 160.4, 141.9, 139.8, 138.0, 135.2, 129.6, 122.0, 114.9, 112.2, 109.3, 94.2, 67.7, 39.6, 23.7, 15.4 |
4b | 8.47(d, J=5.2 Hz, 2H), 7.90(d, J=8.8 Hz, 2H), 7.80(d, J=5.2 Hz, 2H), 6.89—6.94(m, 4H), 4.36(t, J=6.0 Hz, 4H), 3.88(s, 6H), 3.03(s, 6H), 1.79—1.81(m, 4H), 1.51—1.53(m, 4H) | 160.2, 142.4, 140.1, 138.1, 134.6, 130.4, 122.4, 115.0, 111.9, 109.1, 93.6, 68.2, 39.6, 29.3, 23.7, 15.5 |
4c | 8.28(d, J=4.8 Hz, 2H), 7.96(d, J=8.4 Hz, 2H), 7.72(d, J=5.2 Hz, 2H), 6.86—6.91(m, 4H), 4.52(q, J=7.2 Hz, 4H), 4.23(t, 4H, J=4.8 Hz), 3.01(s, 6H), 2.12—2.15(m, 4H), 1.42(t, J=7.2 Hz, 6H) | 160.2, 142.6, 140.5, 138.2, 135.1, 129.3, 122.4, 115.3, 112.2, 109.0, 93.8, 67.9, 39.4, 26.1, 23.3, 15.5 |
4d | 8.27(d, J=4.8 Hz, 2H), 7.96(d, J=8.4 Hz, 2H), 7.73(d, J=5.6 Hz, 2H), 6.86—6.90(m, 4H), 4.53(q, J=7.2 Hz, 4H), 4.12(t, J=6.4 Hz, 4H), 3.03(s, 6H), 1.87—1.92(m, 4H), 1.52—1.62(m, 6H), 1.44(t, J=7.2 Hz, 6H) | 160.5, 142.8, 140.2, 137.7, 134.9, 129.6, 122.4, 115.1, 112.2, 109.2, 93.7, 68.4, 39.4, 29.2, 29.1, 26.0, 22.9, 15.5 |
4e | 8.28(d, J=5.2 Hz, 2H), 7.97(d, J=8.8 Hz, 2H), 7.75(d, J=5.2 Hz, 2H), 6.86—6.91(m, 4H), 4.44(t, J=8.0 Hz, 4H), 4.17(t, J=6.4 Hz, 4H), 3.03(s, 6H), 1.96—2.03(m, 4H), 1.77—1.84(m, 6H), 1.42—1.49(m, 4H), 0.98(t, J=7.2 Hz, 6H) | 160.4, 142.9, 140.3, 137.9, 135.2, 129.3, 121.8, 115.3, 112.4, 109.0, 94.0, 68.7, 44.6, 32.7, 29.3, 26.4, 23.3, 22.1, 14.0 |
4f | 8.29(d, J=5.6 Hz, 2H), 7.99(d, J=8.8 Hz, 2H), 7.82(d, J=5.2 Hz, 2H), 6.87—6.94(m, 2H), 4.47(t, J=8.0 Hz, 4H), 4.15(t, J=6.4 Hz, 4H), 3.11(s, 6H), 1.92—1.99(m, 4H), 1.78—1.86(m, 4H), 1.65—1.69(m, 4H), 1.40—1.50(m, 4H), 0.99(t, J=7.2 Hz, 6H) | 160.3, 143.1, 140.4, 138.0, 135.3, 129.4, 122.3, 115.1, 112.2, 108.9, 94.1, 68.2, 44.6, 32.7, 29.3, 25.9, 23.2, 20.1, 13.9 |
4g | 8.28(d, J=5.6 Hz, 2H), 7.98(d, J=8.8 Hz, 2H), 7.77(d, J=5.2 Hz, 2H), 6.86—6.91(m, 4H), 4.46(t, J=8.0 Hz, 4H), 4.11(t, J=6.4 Hz, 4H), 3.06(s, 6H), 1.85—1.92(m, 4H), 1.78—1.84(m, 4H), 1.52—1.61(m, 4H), 1.40—1.50(m, 8H), 0.98(t, J=7.2 Hz, 6H) | 160.3, 143.1, 140.4, 138.0, 135.3, 129.4, 122.3, 115.1, 112.2, 108.9, 94.1, 68.2, 44.6, 32.7, 29.3, 26.1, 23.3, 20.1, 13.9 |
4h | 8.28(d, J=5.2 Hz, 2H), 7.95(d, J=8.8 Hz, 2H), 7.71(d, J=5.2 Hz, 2H), 6.83—6.89(m, 4H), 4.39(t, J=8.0 Hz, 4H), 4.15(t, J=6.4 Hz, 4H), 3.00(s, 6H), 1.96—2.04(m, 4H), 1.76—1.83(m, 6H), 1.36—1.43(m, 4H), 1.25—1.34(m, 8H), 0.88(t, J=7.2 Hz, 6H) | 160.2, 143.0, 140.5, 138.1, 135.2, 129.3, 122.3, 115.1, 112.2, 108.9, 94.1, 68.2, 44.8, 31.5, 30.5, 29.1, 26.5, 23.3, 22.9, 22.5, 13.9 |
4i | 8.28(d, J=5.2 Hz, 2H), 7.98(d, J=8.4 Hz, 2H), 7.78(d, J=5.6 Hz, 2H), 6.86—6.92(m, 4H), 4.45(t, J=8.0 Hz, 4H), 4.11(t, J=6.4 Hz, 4H), 3.08(s, 6H), 1.78—1.93(m, 8H), 1.53—1.61(m, 4H), 1.40—1.50(m, 8H), 1.31—1.38(m, 8H), 0.89(t, J=7.2 Hz, 6H) | 160.3, 143.1, 140.4, 139.0, 135.2, 131.3, 122.7, 115.1, 112.2, 109.0, 94.0, 68.4, 44.9, 31.5, 30.5, 29.3, 26.5, 26.1, 23.2, 22.5, 13.9 |
4j | 8.28(d, J=5.2 Hz, 2H), 7.99(d, J=8.8 Hz, 2H), 7.77(d, J=5.6 Hz, 2H), 6.90—6.95(m, 4H), 4.43(t, J=8.0 Hz, 4H), 4.38(t, J=6.4 Hz, 4H), 3.04(s, 6H), 2.41—2.47(m, 2H), 1.77—1.85(m, 2H), 1.21—1.45(m, 20H), 0.86(t, J=6.8 Hz, 6H) | 160.0, 143.0, 140.5, 138.1, 135.3, 129.3, 122.3, 115.3, 112.2, 109.0, 94.1, 64.9, 44.9, 31.7, 30.5, 29.5, 29.3, 29.1, 26.9, 23.3, 22.6, 14.0 |
4k | 8.28(d, J=5.2 Hz, 2H), 7.96(d, J=8.4 Hz, 2H), 7.73(d, J=5.2 Hz, 2H), 6.85—6.89(m, 4H), 4.42(t, J=8.0 Hz, 4H), 4.13(t, J=6.4 Hz, 4H), 3.01(s, 6H), 1.91—1.97(m, 4H), 1.77—1.85(m, 4H), 1.64—1.70(m, 4H), 1.23—1.45(m, 20H), 0.87(t, J=7.2 Hz, 6H) | 160.2, 143.0, 140.5, 138.1, 135.3, 129.3, 122.3, 115.1, 112.2, 108.8, 94.1, 68.2, 44.9, 31.7, 30.5, 29.35, 29.32, 29.2, 26.9, 23.4, 22.6, 14.1 |
4l | 8.28(d, J=5.2 Hz, 2H), 7.99(d, J=8.8 Hz, 2H), 7.83(d, J=5.2 Hz, 2H), 6.86—6.93(m, 4H), 4.45(t, J=8.0 Hz, 4H), 4.11(t, J=6.4 Hz, 4H), 3.03(s, 6H), 1.79—1.92(m, 8H), 1.55—1.59(m, 4H), 1.19—1.49(m, 22H), 0.87(t, J=7.2 Hz, 6H) | 160.3, 143.1, 140.4, 137.9, 135.2, 129.4, 122.3, 115.1, 112.2, 109.0, 94.1, 68.4, 44.9, 31.7, 30.5, 29.5, 29.38, 29.32, 29.1, 26.9, 26.1, 23.2, 22.6, 14.0 |
4m | 8.30(d, J=5.6 Hz, 2H), 7.99(d, J=8.8 Hz, 2H), 7.79(d, J=5.2 Hz, 2H), 6.88—6.93(m, 4H), 4.27(d, J=7.6 Hz, 4H), 4.22(t, J=5.6 Hz, 4H), 3.06(s, 6H), 2.21—2.31(m, 2H), 2.12—2.15(m, 4H), 0.94(d, J=6.4 Hz, 12H) | 160.2, 143.8, 140.2, 137.4, 135.4, 129.8, 122.3, 114.9, 112.3, 109.3, 94.8, 67.9,51.8, 30.5, 26.1, 23.1, 20.2 |
4n | 8.29(d, J=5.2 Hz, 2H), 7.95(d, J=8.8 Hz, 2H), 7.74(d, J=5.2 Hz, 2H), 6.87—6.90(m, 4H), 4.27(d, J=7.6 Hz, 4H), 4.10(t, J=6.4 Hz, 4H), 3.01(s, 6H), 2.33—2.43(m, 4H), 2.20—2.31(m, 2H), 1.87—1.94(m, 4H), 1.19—1.57(m, 4H), 0.93(d, J=6.4 Hz, 12H) | 160.5, 143.3, 138.5, 131.2, 122.7, 122.5, 114.7, 112.4, 109.1, 94.8, 94.2, 68.3, 51.0, 30.5, 29.2, 28.8, 26.1, 20.5, 20.1 |
4o | 8.28(d, J=5.2 Hz, 2H), 7.96(d, J=8.8 Hz, 2H), 7.74(d, J=5.2 Hz, 2H), 6.86—6.89(m, 4H), 4.27(d, J=7.6 Hz, 4H), 4.09(t, J=6.4 Hz, 4H), 3.00(s, 6H), 2.21—2.31(m, 2H), 1.83—1.90(m, 4H), 1.49—1.57(m, 4H), 1.35—1.45(m, 8H), 0.94(d, J=6.4 Hz, 12H) | 160.1, 143.6, 140.5, 138.2, 135.6, 129.4, 122.1, 114.9, 112.1, 109.0, 94.8, 68.4, 51.7, 30.5, 29.52, 29.44, 29.36, 26.1, 23.6, 20.2 |
4p | 8.20(d, J=5.6 Hz, 2H), 7.94(d, J=8.8 Hz, 2H), 7.69(d, J=5.2 Hz, 2H), 7.27—7.31(m, 4H), 7.18—7.22(m, 6H), 6.87(dd, J=8.8, 2.0 Hz, 2H), 6.64(d, J=2.0 Hz, 2H), 4.37(t, J=8.0 Hz, 4H), 4.09(t, J=5.2 Hz, 4H), 2.82(s, 6H), 2.71(t, J=7.2 Hz, 4H), 2.05—2.13(m, 8H) | 160.6, 143.2, 141.41, 141.18, 138.5, 135.9, 129.3, 128.8, 126.5, 122.5, 115.3, 112.3, 109.6, 94.0, 68.2, 44.3, 33.2, 32.1, 26.4, 23.4 |
4q | 8.27(d, J=5.6 Hz, 2H), 7.96(d, J=8.4 Hz, 2H), 7.78(d, J=5.2 Hz, 2H), 7.30—7.34(m, 4H), 7.20—7.25(m, 6H), 6.90(dd, J=8.8, 2.0 Hz, 2H), 6.65(d, J=2.0 Hz, 2H), 4.44(t, J=8.0 Hz, 4H), 4.03(t, J=6.4 Hz, 4H), 2.93(s, 6H), 2.76(t, J=7.2 Hz, 4H), 2.12—2.19(m, 4H), 1.90—1.97(m, 4H), 1.64—1.69(m, 4H) | 160.4, 143.0, 140.6, 140.4, 138.0, 135.2, 130.9, 129.5, 128.8, 128.4, 126.3, 122.3, 115.0, 112.2, 109.4, 93.7, 68.1, 44.3, 32.9, 31.7, 29.3, 26.0, 22.6 |
4r | 8.27(d, J=5.2 Hz, 2H), 7.95(d, J=8.4 Hz, 2H), 7.76(d, J=5.6 Hz, 2H), 7.30—7.34(m, 4H), 7.19—7.25(m, 6H), 6.88(dd, J=8.8, 2.0 Hz, 2H), 6.64(d, J=2.0 Hz, 2H), 4.43(t, J=8.0 Hz, 4H), 4.01(t, J=6.4 Hz, 4H), 2.93(s, 6H), 2.76(t, J=7.2 Hz, 4H), 2.11—2.19(m, 4H), 1.87—1.94(m, 4H), 1.51—1.66(m, 6H) | 160.4, 143.1, 140.6, 140.3, 137.8, 135.1, 129.5, 128.6, 128.4, 126.3, 122.3, 114.9, 112.2, 109.4, 93.6, 68.2, 44.0, 32.9, 31.7, 29.28, 29.21, 26.1, 22.8 |
4s | 8.26(d, J=5.2 Hz, 2H), 7.97(d, J=8.8 Hz, 2H), 7.82(d, J=5.2 Hz, 2H), 7.31—7.34(m, 4H), 7.21—7.24(m, 6H), 6.92(dd, J=8.8, 2.0 Hz, 2H), 6.64(d, J=2.0 Hz, 2H), 4.45(t, J=8.0 Hz, 4H), 3.99(t, J=6.4 Hz, 4H), 2.98(s, 6H), 2.78(t, J=7.2 Hz, 4H), 2.12—2.20(m, 4H), 1.83—1.90(m, 4H), 1.84—1.88(m, 4H), 1.50—1.57(m, 4H), 1.37—1.46(m, 8H) | 160.5, 143.2, 140.6, 140.2, 137.5, 135.1, 129.7, 128.6, 128.4, 126.3, 122.4, 114.9, 112.2, 109.6, 93.6, 68.4, 65.8, 44.1, 32.9, 31.7, 29.5, 29.3, 26.1, 22.7 |
Table 4 1H NMR and 13C NMR data of target compounds 4a—4s
Compd. | 1H NMR(400 MHz), δa | 13C NMR(100 MHz), δb |
---|---|---|
4a | 8.27(d, J=5.2 Hz, 2H), 7.97(d, J=8.8 Hz, 2H), 7.74(d, J=5.2 Hz, 2H), 6.89—6.94(m, 4H), 4.36(t, J=6.0 Hz, 4H), 4.07(s, 6H), 3.07(s, 6H), 2.42—2.45(m, 2H) | 160.4, 141.9, 139.8, 138.0, 135.2, 129.6, 122.0, 114.9, 112.2, 109.3, 94.2, 67.7, 39.6, 23.7, 15.4 |
4b | 8.47(d, J=5.2 Hz, 2H), 7.90(d, J=8.8 Hz, 2H), 7.80(d, J=5.2 Hz, 2H), 6.89—6.94(m, 4H), 4.36(t, J=6.0 Hz, 4H), 3.88(s, 6H), 3.03(s, 6H), 1.79—1.81(m, 4H), 1.51—1.53(m, 4H) | 160.2, 142.4, 140.1, 138.1, 134.6, 130.4, 122.4, 115.0, 111.9, 109.1, 93.6, 68.2, 39.6, 29.3, 23.7, 15.5 |
4c | 8.28(d, J=4.8 Hz, 2H), 7.96(d, J=8.4 Hz, 2H), 7.72(d, J=5.2 Hz, 2H), 6.86—6.91(m, 4H), 4.52(q, J=7.2 Hz, 4H), 4.23(t, 4H, J=4.8 Hz), 3.01(s, 6H), 2.12—2.15(m, 4H), 1.42(t, J=7.2 Hz, 6H) | 160.2, 142.6, 140.5, 138.2, 135.1, 129.3, 122.4, 115.3, 112.2, 109.0, 93.8, 67.9, 39.4, 26.1, 23.3, 15.5 |
4d | 8.27(d, J=4.8 Hz, 2H), 7.96(d, J=8.4 Hz, 2H), 7.73(d, J=5.6 Hz, 2H), 6.86—6.90(m, 4H), 4.53(q, J=7.2 Hz, 4H), 4.12(t, J=6.4 Hz, 4H), 3.03(s, 6H), 1.87—1.92(m, 4H), 1.52—1.62(m, 6H), 1.44(t, J=7.2 Hz, 6H) | 160.5, 142.8, 140.2, 137.7, 134.9, 129.6, 122.4, 115.1, 112.2, 109.2, 93.7, 68.4, 39.4, 29.2, 29.1, 26.0, 22.9, 15.5 |
4e | 8.28(d, J=5.2 Hz, 2H), 7.97(d, J=8.8 Hz, 2H), 7.75(d, J=5.2 Hz, 2H), 6.86—6.91(m, 4H), 4.44(t, J=8.0 Hz, 4H), 4.17(t, J=6.4 Hz, 4H), 3.03(s, 6H), 1.96—2.03(m, 4H), 1.77—1.84(m, 6H), 1.42—1.49(m, 4H), 0.98(t, J=7.2 Hz, 6H) | 160.4, 142.9, 140.3, 137.9, 135.2, 129.3, 121.8, 115.3, 112.4, 109.0, 94.0, 68.7, 44.6, 32.7, 29.3, 26.4, 23.3, 22.1, 14.0 |
4f | 8.29(d, J=5.6 Hz, 2H), 7.99(d, J=8.8 Hz, 2H), 7.82(d, J=5.2 Hz, 2H), 6.87—6.94(m, 2H), 4.47(t, J=8.0 Hz, 4H), 4.15(t, J=6.4 Hz, 4H), 3.11(s, 6H), 1.92—1.99(m, 4H), 1.78—1.86(m, 4H), 1.65—1.69(m, 4H), 1.40—1.50(m, 4H), 0.99(t, J=7.2 Hz, 6H) | 160.3, 143.1, 140.4, 138.0, 135.3, 129.4, 122.3, 115.1, 112.2, 108.9, 94.1, 68.2, 44.6, 32.7, 29.3, 25.9, 23.2, 20.1, 13.9 |
4g | 8.28(d, J=5.6 Hz, 2H), 7.98(d, J=8.8 Hz, 2H), 7.77(d, J=5.2 Hz, 2H), 6.86—6.91(m, 4H), 4.46(t, J=8.0 Hz, 4H), 4.11(t, J=6.4 Hz, 4H), 3.06(s, 6H), 1.85—1.92(m, 4H), 1.78—1.84(m, 4H), 1.52—1.61(m, 4H), 1.40—1.50(m, 8H), 0.98(t, J=7.2 Hz, 6H) | 160.3, 143.1, 140.4, 138.0, 135.3, 129.4, 122.3, 115.1, 112.2, 108.9, 94.1, 68.2, 44.6, 32.7, 29.3, 26.1, 23.3, 20.1, 13.9 |
4h | 8.28(d, J=5.2 Hz, 2H), 7.95(d, J=8.8 Hz, 2H), 7.71(d, J=5.2 Hz, 2H), 6.83—6.89(m, 4H), 4.39(t, J=8.0 Hz, 4H), 4.15(t, J=6.4 Hz, 4H), 3.00(s, 6H), 1.96—2.04(m, 4H), 1.76—1.83(m, 6H), 1.36—1.43(m, 4H), 1.25—1.34(m, 8H), 0.88(t, J=7.2 Hz, 6H) | 160.2, 143.0, 140.5, 138.1, 135.2, 129.3, 122.3, 115.1, 112.2, 108.9, 94.1, 68.2, 44.8, 31.5, 30.5, 29.1, 26.5, 23.3, 22.9, 22.5, 13.9 |
4i | 8.28(d, J=5.2 Hz, 2H), 7.98(d, J=8.4 Hz, 2H), 7.78(d, J=5.6 Hz, 2H), 6.86—6.92(m, 4H), 4.45(t, J=8.0 Hz, 4H), 4.11(t, J=6.4 Hz, 4H), 3.08(s, 6H), 1.78—1.93(m, 8H), 1.53—1.61(m, 4H), 1.40—1.50(m, 8H), 1.31—1.38(m, 8H), 0.89(t, J=7.2 Hz, 6H) | 160.3, 143.1, 140.4, 139.0, 135.2, 131.3, 122.7, 115.1, 112.2, 109.0, 94.0, 68.4, 44.9, 31.5, 30.5, 29.3, 26.5, 26.1, 23.2, 22.5, 13.9 |
4j | 8.28(d, J=5.2 Hz, 2H), 7.99(d, J=8.8 Hz, 2H), 7.77(d, J=5.6 Hz, 2H), 6.90—6.95(m, 4H), 4.43(t, J=8.0 Hz, 4H), 4.38(t, J=6.4 Hz, 4H), 3.04(s, 6H), 2.41—2.47(m, 2H), 1.77—1.85(m, 2H), 1.21—1.45(m, 20H), 0.86(t, J=6.8 Hz, 6H) | 160.0, 143.0, 140.5, 138.1, 135.3, 129.3, 122.3, 115.3, 112.2, 109.0, 94.1, 64.9, 44.9, 31.7, 30.5, 29.5, 29.3, 29.1, 26.9, 23.3, 22.6, 14.0 |
4k | 8.28(d, J=5.2 Hz, 2H), 7.96(d, J=8.4 Hz, 2H), 7.73(d, J=5.2 Hz, 2H), 6.85—6.89(m, 4H), 4.42(t, J=8.0 Hz, 4H), 4.13(t, J=6.4 Hz, 4H), 3.01(s, 6H), 1.91—1.97(m, 4H), 1.77—1.85(m, 4H), 1.64—1.70(m, 4H), 1.23—1.45(m, 20H), 0.87(t, J=7.2 Hz, 6H) | 160.2, 143.0, 140.5, 138.1, 135.3, 129.3, 122.3, 115.1, 112.2, 108.8, 94.1, 68.2, 44.9, 31.7, 30.5, 29.35, 29.32, 29.2, 26.9, 23.4, 22.6, 14.1 |
4l | 8.28(d, J=5.2 Hz, 2H), 7.99(d, J=8.8 Hz, 2H), 7.83(d, J=5.2 Hz, 2H), 6.86—6.93(m, 4H), 4.45(t, J=8.0 Hz, 4H), 4.11(t, J=6.4 Hz, 4H), 3.03(s, 6H), 1.79—1.92(m, 8H), 1.55—1.59(m, 4H), 1.19—1.49(m, 22H), 0.87(t, J=7.2 Hz, 6H) | 160.3, 143.1, 140.4, 137.9, 135.2, 129.4, 122.3, 115.1, 112.2, 109.0, 94.1, 68.4, 44.9, 31.7, 30.5, 29.5, 29.38, 29.32, 29.1, 26.9, 26.1, 23.2, 22.6, 14.0 |
4m | 8.30(d, J=5.6 Hz, 2H), 7.99(d, J=8.8 Hz, 2H), 7.79(d, J=5.2 Hz, 2H), 6.88—6.93(m, 4H), 4.27(d, J=7.6 Hz, 4H), 4.22(t, J=5.6 Hz, 4H), 3.06(s, 6H), 2.21—2.31(m, 2H), 2.12—2.15(m, 4H), 0.94(d, J=6.4 Hz, 12H) | 160.2, 143.8, 140.2, 137.4, 135.4, 129.8, 122.3, 114.9, 112.3, 109.3, 94.8, 67.9,51.8, 30.5, 26.1, 23.1, 20.2 |
4n | 8.29(d, J=5.2 Hz, 2H), 7.95(d, J=8.8 Hz, 2H), 7.74(d, J=5.2 Hz, 2H), 6.87—6.90(m, 4H), 4.27(d, J=7.6 Hz, 4H), 4.10(t, J=6.4 Hz, 4H), 3.01(s, 6H), 2.33—2.43(m, 4H), 2.20—2.31(m, 2H), 1.87—1.94(m, 4H), 1.19—1.57(m, 4H), 0.93(d, J=6.4 Hz, 12H) | 160.5, 143.3, 138.5, 131.2, 122.7, 122.5, 114.7, 112.4, 109.1, 94.8, 94.2, 68.3, 51.0, 30.5, 29.2, 28.8, 26.1, 20.5, 20.1 |
4o | 8.28(d, J=5.2 Hz, 2H), 7.96(d, J=8.8 Hz, 2H), 7.74(d, J=5.2 Hz, 2H), 6.86—6.89(m, 4H), 4.27(d, J=7.6 Hz, 4H), 4.09(t, J=6.4 Hz, 4H), 3.00(s, 6H), 2.21—2.31(m, 2H), 1.83—1.90(m, 4H), 1.49—1.57(m, 4H), 1.35—1.45(m, 8H), 0.94(d, J=6.4 Hz, 12H) | 160.1, 143.6, 140.5, 138.2, 135.6, 129.4, 122.1, 114.9, 112.1, 109.0, 94.8, 68.4, 51.7, 30.5, 29.52, 29.44, 29.36, 26.1, 23.6, 20.2 |
4p | 8.20(d, J=5.6 Hz, 2H), 7.94(d, J=8.8 Hz, 2H), 7.69(d, J=5.2 Hz, 2H), 7.27—7.31(m, 4H), 7.18—7.22(m, 6H), 6.87(dd, J=8.8, 2.0 Hz, 2H), 6.64(d, J=2.0 Hz, 2H), 4.37(t, J=8.0 Hz, 4H), 4.09(t, J=5.2 Hz, 4H), 2.82(s, 6H), 2.71(t, J=7.2 Hz, 4H), 2.05—2.13(m, 8H) | 160.6, 143.2, 141.41, 141.18, 138.5, 135.9, 129.3, 128.8, 126.5, 122.5, 115.3, 112.3, 109.6, 94.0, 68.2, 44.3, 33.2, 32.1, 26.4, 23.4 |
4q | 8.27(d, J=5.6 Hz, 2H), 7.96(d, J=8.4 Hz, 2H), 7.78(d, J=5.2 Hz, 2H), 7.30—7.34(m, 4H), 7.20—7.25(m, 6H), 6.90(dd, J=8.8, 2.0 Hz, 2H), 6.65(d, J=2.0 Hz, 2H), 4.44(t, J=8.0 Hz, 4H), 4.03(t, J=6.4 Hz, 4H), 2.93(s, 6H), 2.76(t, J=7.2 Hz, 4H), 2.12—2.19(m, 4H), 1.90—1.97(m, 4H), 1.64—1.69(m, 4H) | 160.4, 143.0, 140.6, 140.4, 138.0, 135.2, 130.9, 129.5, 128.8, 128.4, 126.3, 122.3, 115.0, 112.2, 109.4, 93.7, 68.1, 44.3, 32.9, 31.7, 29.3, 26.0, 22.6 |
4r | 8.27(d, J=5.2 Hz, 2H), 7.95(d, J=8.4 Hz, 2H), 7.76(d, J=5.6 Hz, 2H), 7.30—7.34(m, 4H), 7.19—7.25(m, 6H), 6.88(dd, J=8.8, 2.0 Hz, 2H), 6.64(d, J=2.0 Hz, 2H), 4.43(t, J=8.0 Hz, 4H), 4.01(t, J=6.4 Hz, 4H), 2.93(s, 6H), 2.76(t, J=7.2 Hz, 4H), 2.11—2.19(m, 4H), 1.87—1.94(m, 4H), 1.51—1.66(m, 6H) | 160.4, 143.1, 140.6, 140.3, 137.8, 135.1, 129.5, 128.6, 128.4, 126.3, 122.3, 114.9, 112.2, 109.4, 93.6, 68.2, 44.0, 32.9, 31.7, 29.28, 29.21, 26.1, 22.8 |
4s | 8.26(d, J=5.2 Hz, 2H), 7.97(d, J=8.8 Hz, 2H), 7.82(d, J=5.2 Hz, 2H), 7.31—7.34(m, 4H), 7.21—7.24(m, 6H), 6.92(dd, J=8.8, 2.0 Hz, 2H), 6.64(d, J=2.0 Hz, 2H), 4.45(t, J=8.0 Hz, 4H), 3.99(t, J=6.4 Hz, 4H), 2.98(s, 6H), 2.78(t, J=7.2 Hz, 4H), 2.12—2.20(m, 4H), 1.83—1.90(m, 4H), 1.84—1.88(m, 4H), 1.50—1.57(m, 4H), 1.37—1.46(m, 8H) | 160.5, 143.2, 140.6, 140.2, 137.5, 135.1, 129.7, 128.6, 128.4, 126.3, 122.4, 114.9, 112.2, 109.6, 93.6, 68.4, 65.8, 44.1, 32.9, 31.7, 29.5, 29.3, 26.1, 22.7 |
Compd. | IC50/(μmol·L-1) | ||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
HepG2 | HT-29 | Blu-87 | 22RV1 | 786-0 | MCF-7 | ||||||
4a | 26.0 | 65.4 | 23.2 | 73.3 | >100 | >100 | |||||
4b | 22.1 | 10.9 | 20.7 | 40.4 | 47.4 | 57.0 | |||||
4c | >100 | >100 | >100 | NT | >100 | NT | |||||
4d | >100 | 29.0 | 72.8 | 12.8 | >100 | >100 | |||||
4e | 15.5 | 2.5 | 2.8 | 27.6 | 22.5 | >100 | |||||
4f | 13.0 | 6.1 | 6.1 | 7.6 | >100 | >100 | |||||
4g | 4.2 | 5.3 | 6.3 | 9.2 | 8.3 | 7.4 | |||||
4h | 42.6 | 19.9 | 25.1 | 29.5 | 32.3 | 60.1 | |||||
4i | 57.1 | 14.0 | 32.1 | 15.7 | >100 | >100 | |||||
4j | 11.8 | 3.4 | 13.6 | >100 | 81.9 | 98.5 | |||||
4k | >100 | >100 | >100 | NT | >100 | NT | |||||
4l | 25.6 | 8.2 | 12.1 | >100 | 13.3 | 14.0 | |||||
4m | 12.2 | 13.3 | 2.2 | 1.7 | NT | NT | |||||
4n | 9.9 | 8.4 | 13.3 | 10.3 | 30.5 | 53.0 | |||||
4o | 9.7 | 3.4 | 5.5 | 6.5 | 4.2 | 6.0 | |||||
4p | 12.6 | 8.7 | 9.1 | 7.6 | 7.6 | >100 | |||||
4q | 14.0 | 5.4 | 4.2 | 11.8 | 4.9 | 8.2 | |||||
4r | >100 | >100 | 68.1 | >100 | >100 | NT | |||||
4s | 3.5 | 8.4 | 2.6 | 4.9 | 19.6 | 15.7 | |||||
DDP | 17.2 | 2.5 | 16.4 | 9.4 | 32.7 | 35.8 |
Table 5 Antitumor activity of target compounds in vitro*
Compd. | IC50/(μmol·L-1) | ||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
HepG2 | HT-29 | Blu-87 | 22RV1 | 786-0 | MCF-7 | ||||||
4a | 26.0 | 65.4 | 23.2 | 73.3 | >100 | >100 | |||||
4b | 22.1 | 10.9 | 20.7 | 40.4 | 47.4 | 57.0 | |||||
4c | >100 | >100 | >100 | NT | >100 | NT | |||||
4d | >100 | 29.0 | 72.8 | 12.8 | >100 | >100 | |||||
4e | 15.5 | 2.5 | 2.8 | 27.6 | 22.5 | >100 | |||||
4f | 13.0 | 6.1 | 6.1 | 7.6 | >100 | >100 | |||||
4g | 4.2 | 5.3 | 6.3 | 9.2 | 8.3 | 7.4 | |||||
4h | 42.6 | 19.9 | 25.1 | 29.5 | 32.3 | 60.1 | |||||
4i | 57.1 | 14.0 | 32.1 | 15.7 | >100 | >100 | |||||
4j | 11.8 | 3.4 | 13.6 | >100 | 81.9 | 98.5 | |||||
4k | >100 | >100 | >100 | NT | >100 | NT | |||||
4l | 25.6 | 8.2 | 12.1 | >100 | 13.3 | 14.0 | |||||
4m | 12.2 | 13.3 | 2.2 | 1.7 | NT | NT | |||||
4n | 9.9 | 8.4 | 13.3 | 10.3 | 30.5 | 53.0 | |||||
4o | 9.7 | 3.4 | 5.5 | 6.5 | 4.2 | 6.0 | |||||
4p | 12.6 | 8.7 | 9.1 | 7.6 | 7.6 | >100 | |||||
4q | 14.0 | 5.4 | 4.2 | 11.8 | 4.9 | 8.2 | |||||
4r | >100 | >100 | 68.1 | >100 | >100 | NT | |||||
4s | 3.5 | 8.4 | 2.6 | 4.9 | 19.6 | 15.7 | |||||
DDP | 17.2 | 2.5 | 16.4 | 9.4 | 32.7 | 35.8 |
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