高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (4): 674.doi: 10.7503/cjcu20170636
刘莉1, 马洋洋2, 王宽1, 贾云静2, 李婉2, 朱华结2()
收稿日期:
2017-09-21
出版日期:
2018-04-10
发布日期:
2018-03-18
作者简介:
联系人简介: 朱华结, 男, 博士, 教授, 博士生导师, 主要从事手性计算、 合成及新药研发筛选研究. E-mail:基金资助:
LIU Li1, MA Yangyang2, WANG Kuan1, JIA Yunjing2, LI Wan2, ZHU Huajie2,*()
Received:
2017-09-21
Online:
2018-04-10
Published:
2018-03-18
Contact:
ZHU Huajie
E-mail:zhuhuajie@hotmail.com
Supported by:
摘要:
以L-色氨酸为原料合成了72个不同取代基的β-咔啉化合物, 其中31个新化合物, 包括12对手性化合物. 采用噻唑蓝(MTT)法对5种肿瘤细胞株及5种菌株进行了体外抗肿瘤活性、 抗菌活性的筛选及构效关系研究. 生物活性测试结果表明, 部分目标化合物具有一定的抗肿瘤活性(化合物3b对A549细胞的IC50=3.17 μmol/L), 且具有不同程度的抑菌活性(化合物5h对鳗弧菌的MIC=0.78 μmol/L).
中图分类号:
TrendMD:
刘莉, 马洋洋, 王宽, 贾云静, 李婉, 朱华结. β-咔啉衍生物的抗肿瘤及抗菌活性. 高等学校化学学报, 2018, 39(4): 674.
LIU Li, MA Yangyang, WANG Kuan, JIA Yunjing, LI Wan, ZHU Huajie. Anti-tumor and Antimicrobial Activities of β-Carbolines†. Chem. J. Chinese Universities, 2018, 39(4): 674.
Compd. | Appearance | Yield(%) | Elemental analysis(%, cacld. ) | ||
---|---|---|---|---|---|
C | H | N | |||
5b | Yellow oil | 86 | 70.73(70.70) | 4.69(4.68) | 8.72(8.68) |
5c | Yellow oil | 85 | 70.73(70.70) | 4.69(4.68) | 8.72(8.68) |
5d | Yellow oil | 93 | 79.41(79.44) | 6.03(6.00) | 9.27(9.26) |
5f | Yellow oil | 89 | 74.54(74.50) | 4.91(4.94) | 9.13(9.14) |
5j | Yellow oil | 90 | 75.41(75.45) | 5.73(5.70) | 8.83(8.80) |
5k | Yellow oil | 85 | 68.49(68.46) | 4.53(4.54) | 12.63(12.61) |
5l | Yellow oil | 87 | 77.49(77.52) | 7.54(7.53) | 9.55(9.52) |
7a | Yellow oil | 89 | 80.67(80.71) | 5.83(5.85) | 8.59(8.56) |
7b | Yellow oil | 73 | 73.05(73.02) | 5.05(5.01) | 7.73(7.74) |
7c | Yellow oil | 63 | 73.05(73.02) | 5.05(5.01) | 7.73(7.74) |
7d | Yellow oil | 55 | 80.89(80.91) | 6.17(6.20) | 8.23(8.20) |
7e | Yellow oil | 48 | 76.47(76.50) | 5.27(5.25) | 8.13(8.11) |
7f | Yellow oil | 61 | 76.49(76.50) | 5.29(5.25) | 8.11(8.11) |
7g | Yellow oil | 56 | 82.77(82.73) | 5.64(5.61) | 7.39(7.42) |
7h | Yellow oil | 77 | 82.75(82.73) | 5.63(5.61) | 7.38(7.42) |
7i | Yellow oil | 69 | 77.27(77.29) | 5.97(5.92) | 7.83(7.84) |
7j | Yellow oil | 77 | 77.26(77.29) | 5.95(5.92) | 7.81(7.84) |
7k | Yellow oil | 79 | 70.93(70.96) | 4.85(4.87) | 11.24(11.28) |
7l | Yellow oil | 86 | 79.21(79.24) | 7.58(7.56) | 8.39(8.40) |
Table 1 Appearance, yields and elemental analysis data of new compounds involved
Compd. | Appearance | Yield(%) | Elemental analysis(%, cacld. ) | ||
---|---|---|---|---|---|
C | H | N | |||
5b | Yellow oil | 86 | 70.73(70.70) | 4.69(4.68) | 8.72(8.68) |
5c | Yellow oil | 85 | 70.73(70.70) | 4.69(4.68) | 8.72(8.68) |
5d | Yellow oil | 93 | 79.41(79.44) | 6.03(6.00) | 9.27(9.26) |
5f | Yellow oil | 89 | 74.54(74.50) | 4.91(4.94) | 9.13(9.14) |
5j | Yellow oil | 90 | 75.41(75.45) | 5.73(5.70) | 8.83(8.80) |
5k | Yellow oil | 85 | 68.49(68.46) | 4.53(4.54) | 12.63(12.61) |
5l | Yellow oil | 87 | 77.49(77.52) | 7.54(7.53) | 9.55(9.52) |
7a | Yellow oil | 89 | 80.67(80.71) | 5.83(5.85) | 8.59(8.56) |
7b | Yellow oil | 73 | 73.05(73.02) | 5.05(5.01) | 7.73(7.74) |
7c | Yellow oil | 63 | 73.05(73.02) | 5.05(5.01) | 7.73(7.74) |
7d | Yellow oil | 55 | 80.89(80.91) | 6.17(6.20) | 8.23(8.20) |
7e | Yellow oil | 48 | 76.47(76.50) | 5.27(5.25) | 8.13(8.11) |
7f | Yellow oil | 61 | 76.49(76.50) | 5.29(5.25) | 8.11(8.11) |
7g | Yellow oil | 56 | 82.77(82.73) | 5.64(5.61) | 7.39(7.42) |
7h | Yellow oil | 77 | 82.75(82.73) | 5.63(5.61) | 7.38(7.42) |
7i | Yellow oil | 69 | 77.27(77.29) | 5.97(5.92) | 7.83(7.84) |
7j | Yellow oil | 77 | 77.26(77.29) | 5.95(5.92) | 7.81(7.84) |
7k | Yellow oil | 79 | 70.93(70.96) | 4.85(4.87) | 11.24(11.28) |
7l | Yellow oil | 86 | 79.21(79.24) | 7.58(7.56) | 8.39(8.40) |
Compd. | 1H NMR(CDCl3, 600 MHz), δ | 13C NMR(CDCl3, 150 MHz), δ |
---|---|---|
5b | 8.17(d, J=7.8 Hz, 1H), 7.95(s, 1H), 7.64-7.59(m, 3H), 7.52(d, J=8.4 Hz, 2H), 7.43(d, J=8.3 Hz, 1H), 7.32(t, J=7.5 Hz, 1H), 4.96(s, 2H), 3.49(s, 3H) | 145.12(s), 143.90(s), 137.50(s), 136.75(s), 134.54(s), 132.11(s), 131.65(s), 131.00(s), 128.42(s), 126.16(s), 122.12(s), 121.54(s), 118.68(s), 113.44(s), 109.74(s), 60.18(s), 32.27(s) |
5c | 8.09(d, J=7.8 Hz, 1H), 7.89(s, 1H), 7.60(s, 1H), 7.55(t, J=7.7 Hz, 1H), 7.46(t, J=7.4 Hz, 1H), 7.40(d, J=6.7 Hz, 2H), 7.36(d, J=8.3 Hz, 1H), 7.25(t, J=7.4 Hz, 1H), 4.89(s, 2H), 3.42(s, 3H) | 147.93, 143.64, 141.35, 141.09, 134.56, 134.24, 131.62, 129.88, 129.43, 128.89, 128.63, 127.93, 121.66, 121.03, 120.07, 110.61, 109.87, 64.77, 33.15 |
5d | 8.15(d, J=7.8 Hz, 1H), 7.90(s, 1H), 7.60(t, J=7.6 Hz, 1H), 7.53(d, J=7.7 Hz, 2H), 7.41(d, J=8.2 Hz, 1H), 7.33(d, J=7.6 Hz, 2H), 7.29(t, J=7.5 Hz, 1H), 4.94(s, 2H), 3.46(d, J=12.7 Hz, 3H), 2.46(s, 3H) | 147.60(s), 143.56(s), 142.98(s), 138.39(s), 136.69(s), 134.61(s), 131.20(s), 129.61(s), 128.87(s), 128.61(s), 121.60(s), 121.09(s), 119.81(s), 109.97(s), 109.81(s), 64.69(s), 32.95(s), 21.41(s) |
5f | 8.15(d, J=7.8 Hz, 1H), 7.93(s, 1H), 7.61(dd, J=10.6, 5.4 Hz, 3H), 7.41(d, J=8.3 Hz, 1H), 7.31(t, J=7.5 Hz, 1H), 7.21(t, J=8.5 Hz, 2H), 4.95(s, 2H), 3.46(s, 3H) | 163.82(s), 162.18(s), 147.93(s), 143.61(s), 141.72(s), 135.67(s), 134.60(s), 131.47(d, J=8.0 Hz), 128.80(s), 121.64(s), 121.06(s), 120.00(s), 115.31(s), 115.22(d, J=21.4 Hz), 110.39(s), 109.83(s), 64.78(s), 32.99(s) |
5j | 8.14(t, J=8.7 Hz, 1H), 7.93(s, 1H), 7.60(t, J=7.7 Hz, 1H), 7.46-7.37(m, 2H), 7.34-7.28(m, 1H), 7.19(d, J=7.3 Hz, 2H), 7.07-7.02(m, 1H), 4.99-4.92(m, 2H), 3.85(d, J=21.5 Hz, 3H), 3.47(s, 3H) | 159.44(s), 147.70(s), 143.54(s), 142.69(s), 140.90(s), 134.48(s), 131.24(s), 129.21(s), 128.67(s), 122.26(s), 121.60(s), 121.06(s), 119.86(s), 115.05(s), 114.46(s), 110.31(s), 109.80(s), 64.82(s), 55.41(s), 32.81(s) |
5k | 8.41(d, J=8.6 Hz, 2H), 8.18(d, J=7.8 Hz, 1H), 8.00(d, J=10.9 Hz, 1H), 7.87(d, J=8.5 Hz, 2H), 7.65(t, J=7.6 Hz, 1H), 7.45(d, J=8.3 Hz, 1H), 7.35(t, J=7.5 Hz, 1H), 4.98(s, 2H), 3.49(d, J=9.5 Hz, 3H) | 147.24(s), 146.78(s), 143.30(s), 137.93(s), 133.40(s), 131.96(s), 130.03(s), 129.03(s), 122.54(s) 121.06(s), 119.92(s), 119.73(s), 111.00(s), 109.13(s), 62.96(s), 32.47(s) |
5l | 8.08(d, J=7.8 Hz, 1H), 7.68(s, 1H), 7.59(t, J=7.6 Hz, 1H), 7.44(d, J=8.3 Hz, 1H), 7.24(s, 1H), 4.88(s, 2H), 4.11(d, J=11.2 Hz, 3H), 3.55(t, J=11.2 Hz, 1H), 1.98(dd, J=38.0, 10.3 Hz, 6H), 1.55-1.38(m, 4H) | 148.64(s), 146.41(s), 143.04(s), 134.09(s), 130.71(s), 128.28(s), 121.31(s), 121.13(s), 119.47(s), 109.44(s), 108.31(s), 63.91(s), 32.93(s), 32.65(s), 29.69(s), 26.76(s), 26.15(s) |
7a | 8.13(d, J=1.8 Hz, 1H), 7.90(s, 1H), 7.64(d, J=6.6 Hz, 2H), 7.60-7.41(m, 5H), 7.33(d, J=8.7 Hz, 1H), 5.92(ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.20-5.10(m, 2H), 5.03(dd, J=7.3, 4.9 Hz, 1H), 3.45(s, 3H), 2.79-2.73(m, 1H), 2.62(dt, J=14.4, 7.3 Hz, 1H) | 150.51, 142.87, 141.86, 139.29, 134.90, 134.78, 130.22, 129.76, 128.80, 128.65, 128.20, 125.41, 122.22, 121.23, 117.74, 110.93, 109.84, 77.23, 77.02, 76.81, 72.51, 43.53, 33.12 |
7b | 8.10(d, J=7.8 Hz, 1H), 7.89(s, 1H), 7.61-7.52(m, 3H), 7.45(t, J=7.2 Hz, 2H), 7.35(t, J=6.9 Hz, 1H), 7.25(t, J=7.5 Hz, 1H), 5.86(ddt, J=17.2, 10.2, 7.1 Hz, 1H), 5.07(dd, J=27.4, 13.6 Hz, 2H), 4.98-4.94(m, 1H), 3.41(d, J=16.5 Hz, 3H), 2.73-2.67(m, 1H), 2.55(dt, J=14.4, 7.3 Hz, 1H) | 149.34, 142.69, 139.92, 133.80, 133.63, 133.55, 130.54, 130.12, 127.82, 127.39, 120.63, 120.13, 119.02, 116.69, 109.01, 108.85, 71.46, 42.55, 32.18 |
7c | 8.18(d, J=7.8 Hz, 1H), 7.99(s, 1H), 7.67(s, 1H), 7.63(t, J=7.7 Hz, 1H), 7.55(t, J=7.1 Hz, 1H), 7.50-7.45(m, 2H), 7.43(d, J=8.3 Hz, 1H), 7.33(t, J=7.5 Hz, 1H), 5.93(ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.19-5.10(m, 2H), 5.05(dd, J=7.1, 4.9 Hz, 1H), 3.50(s, 3H), 2.80-2.75(m, 1H), 2.63(dt, J=14.3, 7.3 Hz, 1H) | 143.76, 140.57, 134.75, 134.51, 134.20, 131.69, 129.95, 129.43, 128.97, 128.67, 128.03, 121.70, 121.08, 120.12, 117.80, 110.29, 109.89, 72.51, 53.41, 43.51, 33.17 |
7d | 8.17(d, J=7.8 Hz, 1H), 7.93(s, 1H), 7.61(t, J=7.7 Hz, 1H), 7.55(d, J=7.8 Hz, 2H), 7.42(d, J=8.3 Hz, 1H), 7.35-7.28(m, 3H), 5.94(ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.13(dd, J=29.9, 13.6 Hz, 2H), 5.04-4.99(m, 1H), 3.49(s, 3H), 2.79-2.74(m, 1H), 2.62(dt, J=14.4, 7.3 Hz, 1H), 2.48(s, 3H) | 150.04, 143.66, 138.38, 135.00, 134.59, 131.21, 129.69, 128.83, 128.58, 121.58, 121.20, 119.80, 117.50, 109.81, 109.53, 72.43, 43.61, 33.00, 21.39 |
Compd. | 1H NMR(CDCl3, 600 MHz), δ | 13C NMR(CDCl3, 150 MHz), δ |
7e | 8.17(d, J=7.8 Hz, 1H), 7.96(s, 1H), 7.63(ddd, J=15.0, 6.8, 1.4 Hz, 3H), 7.42(d, J=8.3 Hz, 1H), 7.32(t, J=7.5 Hz, 1H), 7.23(t, J=8.6 Hz, 2H), 5.93(ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.19-5.09(m, 2H), 5.03(dd, J=7.4, 4.8 Hz, 1H), 3.48(s, 3H), 2.80-2.73(m, 1H), 2.62(dt, J=14.4, 7.4 Hz, 1H) | 162.82, 161.18, 149.29, 142.69, 140.24, 134.71, 133.84, 133.60, 130.54, 130.49, 127.76, 120.62, 120.16, 118.97, 116.65, 114.24, 114.10, 108.88, 108.83, 71.51, 42.55, 32.04 |
7f | 8.17(d, J=7.8 Hz, 1H), 7.96(s, 1H), 7.67-7.59(m, 3H), 7.42(d, J=8.3 Hz, 1H), 7.32(t, J=7.5 Hz, 1H), 7.23(t, J=8.6 Hz, 2H), 5.93(ddt, J=17.2, 10.1, 7.0 Hz, 1H), 5.14(dd, J=27.9, 13.7 Hz, 2H), 5.03(dd, J=7.3, 4.8 Hz, 1H), 3.48(s, 3H), 2.80-2.73(m, 1H), 2.62(dt, J=14.5, 7.3 Hz, 1H) | 163.84, 162.19, 150.29, 143.70, 141.24, 134.85, 134.61, 131.55, 131.50, 131.46, 128.78, 121.64, 121.17, 119.99, 117.67, 115.25, 115.11, 109.89, 109.84, 72.52, 43.56, 33.05 |
7g | 8.26(d, J=8.0 Hz, 1H), 8.10(d, J=5.0 Hz, 1H), 8.04(d, J=8.9 Hz, 1H), 7.99(d, J=8.2 Hz, 1H), 7.70-7.64(m, 2H), 7.62(t, J=7.7 Hz, 1H), 7.56-7.51(m, 1H), 7.43(t, J=8.2 Hz, 1H), 7.38(dd, J=13.2, 5.9 Hz, 1H), 7.34(dd, J=7.7, 5.5 Hz, 2H), 6.02-5.91(m, 1H), 5.22-5.08(m, 3H), 3.10(s, 3H), 2.83(ddd, J=19.9, 13.8, 5.8 Hz, 1H), 2.67(td, J=14.0, 7.0 Hz, 1H) | 149.19, 142.14, 139.97, 134.40, 133.88, 133.81, 132.44, 131.79, 129.63, 127.98, 127.64, 127.34, 126.95, 125.63, 125.16, 124.94, 124.17, 120.67, 120.00, 118.77, 116.67, 109.11, 108.60, 71.64, 42.67, 30.32 |
7h | 8.23(d, J=8.0 Hz, 1H), 8.07(d, J=4.6 Hz, 1H), 8.03-7.99(m, 1H), 7.96(d, J=8.2 Hz, 1H), 7.66-7.62(m, 2H), 7.59(t, J=7.7 Hz, 1H), 7.53-7.48(m, 1H), 7.41(t, J=8.1 Hz, 1H), 7.35(dd, J=13.4, 5.9 Hz, 1H), 7.34-7.29(m, 2H), 5.98-5.89(m, 1H), 5.12(ddd, J=21.6, 14.3, 9.2 Hz, 3H), 3.07(s, 3H), 2.84-2.76(m, 1H), 2.64(dq, J=13.8, 6.9 Hz, 1H) | 150.28, 143.12, 141.04, 136.96, 135.43, 134.85, 133.47, 132.82, 130.58, 128.96, 128.61, 128.35, 127.88, 126.66, 126.16, 125.98, 125.19, 121.67, 121.04, 119.76, 117.66, 110.08, 109.61, 72.78, 43.74, 31.35 |
7i | 8.17(d, J=7.8 Hz, 1H), 7.92(s, 1H), 7.61(dd, J=19.8, 10.6 Hz, 3H), 7.42(d, J=8.3 Hz, 1H), 7.30(t, J=7.5 Hz, 1H), 7.06(d, J=8.5 Hz, 2H), 5.94(ddt, J=17.1, 10.1, 7.0 Hz, 1H), 5.14(dd, J=30.2, 13.6 Hz, 2H), 5.03(dd, J=7.3, 4.8 Hz, 1H), 3.91(s, 3H), 3.51(s, 3H), 2.80-2.74(m, 1H), 2.62(dt, J=14.4, 7.3 Hz, 1H) | 159.95, 150.06, 143.72, 142.20, 134.98, 134.63, 131.27, 131.03, 128.62, 121.60, 121.22, 119.83, 117.53, 113.62, 109.84, 109.47, 72.44, 55.42, 43.56, 33.01 |
7j | 8.18(d, J=7.8 Hz, 1H), 7.96(s, 1H), 7.66-7.58(m, 1H), 7.46-7.39(m, 2H), 7.30(dd, J=18.7, 11.3 Hz, 1H), 7.21(dd, J=8.0, 4.8 Hz, 2H), 7.05(dd, J=8.3, 2.1 Hz, 1H), 5.94(ddt, J=17.1, 10.1, 7.0 Hz, 1H), 5.14(dd, J=29.4, 13.7 Hz, 2H), 5.04(dd, J=7.4, 4.8 Hz, 1H), 3.89(s, 3H), 3.49(s, 3H), 2.81-2.74(m, 1H), 2.62(dt, J=14.4, 7.4 Hz, 1H) | 159.41, 150.07, 143.64, 142.15, 134.95, 134.48, 131.26, 129.16, 128.68, 122.35, 121.61, 121.14, 119.87, 117.61, 115.21, 114.36, 109.84, 109.82, 72.52, 55.42, 43.59, 32.89, 29.70 |
7k | 8.41(d, J=8.6 Hz, 2H), 8.19(d, J=7.8 Hz, 1H), 8.03(s, 1H), 7.89-7.86(m, 2H), 7.67-7.63(m, 1H), 7.45(d, J=8.3 Hz, 1H), 7.35(t, J=7.5 Hz, 1H), 5.92(ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.19-5.11(m, 2H), 5.05(dd, J=7.3, 4.8 Hz, 1H), 3.50(s, 3H), 2.81-2.75(m, 1H), 2.63(dt, J=14.4, 7.3 Hz, 1H) | 167.71, 150.86, 147.83, 146.02, 143.85, 139.34, 134.73, 134.58, 132.12, 130.79, 129.22, 123.42, 121.77, 121.13, 120.42, 117.95, 110.87, 109.98, 72.53, 43.50, 33.57 |
7l | 8.03(d, J=7.7 Hz, 1H), 7.64(s, 1H), 7.52(t, J=7.6 Hz, 1H), 7.37(d, J=8.3 Hz, 1H), 7.22-7.16(m, 2H), 5.83(ddt, J=17.1, 10.2, 7.0 Hz, 1H), 5.08-4.98(m, 2H), 4.90-4.85(m, 1H), 3.51-3.42(m, 1H), 2.67-2.59(m, 1H), 2.50(dt, J=13.8, 6.8 Hz, 1H), 1.99-1.83(m, 7H), 1.76(d, J=12.7 Hz, 1H), 1.46-1.41(m, 2H), 1.35-1.30(m, 1H) | 147.95, 147.27, 141.97, 134.02, 132.95, 129.55, 127.21, 120.29, 120.20, 118.44, 116.12, 108.41, 107.31, 70.98, 42.73, 41.04, 31.93, 31.88, 31.61, 28.68, 25.72, 25.14 |
Table 2 1H NMR and 13C NMR data of new compounds involved
Compd. | 1H NMR(CDCl3, 600 MHz), δ | 13C NMR(CDCl3, 150 MHz), δ |
---|---|---|
5b | 8.17(d, J=7.8 Hz, 1H), 7.95(s, 1H), 7.64-7.59(m, 3H), 7.52(d, J=8.4 Hz, 2H), 7.43(d, J=8.3 Hz, 1H), 7.32(t, J=7.5 Hz, 1H), 4.96(s, 2H), 3.49(s, 3H) | 145.12(s), 143.90(s), 137.50(s), 136.75(s), 134.54(s), 132.11(s), 131.65(s), 131.00(s), 128.42(s), 126.16(s), 122.12(s), 121.54(s), 118.68(s), 113.44(s), 109.74(s), 60.18(s), 32.27(s) |
5c | 8.09(d, J=7.8 Hz, 1H), 7.89(s, 1H), 7.60(s, 1H), 7.55(t, J=7.7 Hz, 1H), 7.46(t, J=7.4 Hz, 1H), 7.40(d, J=6.7 Hz, 2H), 7.36(d, J=8.3 Hz, 1H), 7.25(t, J=7.4 Hz, 1H), 4.89(s, 2H), 3.42(s, 3H) | 147.93, 143.64, 141.35, 141.09, 134.56, 134.24, 131.62, 129.88, 129.43, 128.89, 128.63, 127.93, 121.66, 121.03, 120.07, 110.61, 109.87, 64.77, 33.15 |
5d | 8.15(d, J=7.8 Hz, 1H), 7.90(s, 1H), 7.60(t, J=7.6 Hz, 1H), 7.53(d, J=7.7 Hz, 2H), 7.41(d, J=8.2 Hz, 1H), 7.33(d, J=7.6 Hz, 2H), 7.29(t, J=7.5 Hz, 1H), 4.94(s, 2H), 3.46(d, J=12.7 Hz, 3H), 2.46(s, 3H) | 147.60(s), 143.56(s), 142.98(s), 138.39(s), 136.69(s), 134.61(s), 131.20(s), 129.61(s), 128.87(s), 128.61(s), 121.60(s), 121.09(s), 119.81(s), 109.97(s), 109.81(s), 64.69(s), 32.95(s), 21.41(s) |
5f | 8.15(d, J=7.8 Hz, 1H), 7.93(s, 1H), 7.61(dd, J=10.6, 5.4 Hz, 3H), 7.41(d, J=8.3 Hz, 1H), 7.31(t, J=7.5 Hz, 1H), 7.21(t, J=8.5 Hz, 2H), 4.95(s, 2H), 3.46(s, 3H) | 163.82(s), 162.18(s), 147.93(s), 143.61(s), 141.72(s), 135.67(s), 134.60(s), 131.47(d, J=8.0 Hz), 128.80(s), 121.64(s), 121.06(s), 120.00(s), 115.31(s), 115.22(d, J=21.4 Hz), 110.39(s), 109.83(s), 64.78(s), 32.99(s) |
5j | 8.14(t, J=8.7 Hz, 1H), 7.93(s, 1H), 7.60(t, J=7.7 Hz, 1H), 7.46-7.37(m, 2H), 7.34-7.28(m, 1H), 7.19(d, J=7.3 Hz, 2H), 7.07-7.02(m, 1H), 4.99-4.92(m, 2H), 3.85(d, J=21.5 Hz, 3H), 3.47(s, 3H) | 159.44(s), 147.70(s), 143.54(s), 142.69(s), 140.90(s), 134.48(s), 131.24(s), 129.21(s), 128.67(s), 122.26(s), 121.60(s), 121.06(s), 119.86(s), 115.05(s), 114.46(s), 110.31(s), 109.80(s), 64.82(s), 55.41(s), 32.81(s) |
5k | 8.41(d, J=8.6 Hz, 2H), 8.18(d, J=7.8 Hz, 1H), 8.00(d, J=10.9 Hz, 1H), 7.87(d, J=8.5 Hz, 2H), 7.65(t, J=7.6 Hz, 1H), 7.45(d, J=8.3 Hz, 1H), 7.35(t, J=7.5 Hz, 1H), 4.98(s, 2H), 3.49(d, J=9.5 Hz, 3H) | 147.24(s), 146.78(s), 143.30(s), 137.93(s), 133.40(s), 131.96(s), 130.03(s), 129.03(s), 122.54(s) 121.06(s), 119.92(s), 119.73(s), 111.00(s), 109.13(s), 62.96(s), 32.47(s) |
5l | 8.08(d, J=7.8 Hz, 1H), 7.68(s, 1H), 7.59(t, J=7.6 Hz, 1H), 7.44(d, J=8.3 Hz, 1H), 7.24(s, 1H), 4.88(s, 2H), 4.11(d, J=11.2 Hz, 3H), 3.55(t, J=11.2 Hz, 1H), 1.98(dd, J=38.0, 10.3 Hz, 6H), 1.55-1.38(m, 4H) | 148.64(s), 146.41(s), 143.04(s), 134.09(s), 130.71(s), 128.28(s), 121.31(s), 121.13(s), 119.47(s), 109.44(s), 108.31(s), 63.91(s), 32.93(s), 32.65(s), 29.69(s), 26.76(s), 26.15(s) |
7a | 8.13(d, J=1.8 Hz, 1H), 7.90(s, 1H), 7.64(d, J=6.6 Hz, 2H), 7.60-7.41(m, 5H), 7.33(d, J=8.7 Hz, 1H), 5.92(ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.20-5.10(m, 2H), 5.03(dd, J=7.3, 4.9 Hz, 1H), 3.45(s, 3H), 2.79-2.73(m, 1H), 2.62(dt, J=14.4, 7.3 Hz, 1H) | 150.51, 142.87, 141.86, 139.29, 134.90, 134.78, 130.22, 129.76, 128.80, 128.65, 128.20, 125.41, 122.22, 121.23, 117.74, 110.93, 109.84, 77.23, 77.02, 76.81, 72.51, 43.53, 33.12 |
7b | 8.10(d, J=7.8 Hz, 1H), 7.89(s, 1H), 7.61-7.52(m, 3H), 7.45(t, J=7.2 Hz, 2H), 7.35(t, J=6.9 Hz, 1H), 7.25(t, J=7.5 Hz, 1H), 5.86(ddt, J=17.2, 10.2, 7.1 Hz, 1H), 5.07(dd, J=27.4, 13.6 Hz, 2H), 4.98-4.94(m, 1H), 3.41(d, J=16.5 Hz, 3H), 2.73-2.67(m, 1H), 2.55(dt, J=14.4, 7.3 Hz, 1H) | 149.34, 142.69, 139.92, 133.80, 133.63, 133.55, 130.54, 130.12, 127.82, 127.39, 120.63, 120.13, 119.02, 116.69, 109.01, 108.85, 71.46, 42.55, 32.18 |
7c | 8.18(d, J=7.8 Hz, 1H), 7.99(s, 1H), 7.67(s, 1H), 7.63(t, J=7.7 Hz, 1H), 7.55(t, J=7.1 Hz, 1H), 7.50-7.45(m, 2H), 7.43(d, J=8.3 Hz, 1H), 7.33(t, J=7.5 Hz, 1H), 5.93(ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.19-5.10(m, 2H), 5.05(dd, J=7.1, 4.9 Hz, 1H), 3.50(s, 3H), 2.80-2.75(m, 1H), 2.63(dt, J=14.3, 7.3 Hz, 1H) | 143.76, 140.57, 134.75, 134.51, 134.20, 131.69, 129.95, 129.43, 128.97, 128.67, 128.03, 121.70, 121.08, 120.12, 117.80, 110.29, 109.89, 72.51, 53.41, 43.51, 33.17 |
7d | 8.17(d, J=7.8 Hz, 1H), 7.93(s, 1H), 7.61(t, J=7.7 Hz, 1H), 7.55(d, J=7.8 Hz, 2H), 7.42(d, J=8.3 Hz, 1H), 7.35-7.28(m, 3H), 5.94(ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.13(dd, J=29.9, 13.6 Hz, 2H), 5.04-4.99(m, 1H), 3.49(s, 3H), 2.79-2.74(m, 1H), 2.62(dt, J=14.4, 7.3 Hz, 1H), 2.48(s, 3H) | 150.04, 143.66, 138.38, 135.00, 134.59, 131.21, 129.69, 128.83, 128.58, 121.58, 121.20, 119.80, 117.50, 109.81, 109.53, 72.43, 43.61, 33.00, 21.39 |
Compd. | 1H NMR(CDCl3, 600 MHz), δ | 13C NMR(CDCl3, 150 MHz), δ |
7e | 8.17(d, J=7.8 Hz, 1H), 7.96(s, 1H), 7.63(ddd, J=15.0, 6.8, 1.4 Hz, 3H), 7.42(d, J=8.3 Hz, 1H), 7.32(t, J=7.5 Hz, 1H), 7.23(t, J=8.6 Hz, 2H), 5.93(ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.19-5.09(m, 2H), 5.03(dd, J=7.4, 4.8 Hz, 1H), 3.48(s, 3H), 2.80-2.73(m, 1H), 2.62(dt, J=14.4, 7.4 Hz, 1H) | 162.82, 161.18, 149.29, 142.69, 140.24, 134.71, 133.84, 133.60, 130.54, 130.49, 127.76, 120.62, 120.16, 118.97, 116.65, 114.24, 114.10, 108.88, 108.83, 71.51, 42.55, 32.04 |
7f | 8.17(d, J=7.8 Hz, 1H), 7.96(s, 1H), 7.67-7.59(m, 3H), 7.42(d, J=8.3 Hz, 1H), 7.32(t, J=7.5 Hz, 1H), 7.23(t, J=8.6 Hz, 2H), 5.93(ddt, J=17.2, 10.1, 7.0 Hz, 1H), 5.14(dd, J=27.9, 13.7 Hz, 2H), 5.03(dd, J=7.3, 4.8 Hz, 1H), 3.48(s, 3H), 2.80-2.73(m, 1H), 2.62(dt, J=14.5, 7.3 Hz, 1H) | 163.84, 162.19, 150.29, 143.70, 141.24, 134.85, 134.61, 131.55, 131.50, 131.46, 128.78, 121.64, 121.17, 119.99, 117.67, 115.25, 115.11, 109.89, 109.84, 72.52, 43.56, 33.05 |
7g | 8.26(d, J=8.0 Hz, 1H), 8.10(d, J=5.0 Hz, 1H), 8.04(d, J=8.9 Hz, 1H), 7.99(d, J=8.2 Hz, 1H), 7.70-7.64(m, 2H), 7.62(t, J=7.7 Hz, 1H), 7.56-7.51(m, 1H), 7.43(t, J=8.2 Hz, 1H), 7.38(dd, J=13.2, 5.9 Hz, 1H), 7.34(dd, J=7.7, 5.5 Hz, 2H), 6.02-5.91(m, 1H), 5.22-5.08(m, 3H), 3.10(s, 3H), 2.83(ddd, J=19.9, 13.8, 5.8 Hz, 1H), 2.67(td, J=14.0, 7.0 Hz, 1H) | 149.19, 142.14, 139.97, 134.40, 133.88, 133.81, 132.44, 131.79, 129.63, 127.98, 127.64, 127.34, 126.95, 125.63, 125.16, 124.94, 124.17, 120.67, 120.00, 118.77, 116.67, 109.11, 108.60, 71.64, 42.67, 30.32 |
7h | 8.23(d, J=8.0 Hz, 1H), 8.07(d, J=4.6 Hz, 1H), 8.03-7.99(m, 1H), 7.96(d, J=8.2 Hz, 1H), 7.66-7.62(m, 2H), 7.59(t, J=7.7 Hz, 1H), 7.53-7.48(m, 1H), 7.41(t, J=8.1 Hz, 1H), 7.35(dd, J=13.4, 5.9 Hz, 1H), 7.34-7.29(m, 2H), 5.98-5.89(m, 1H), 5.12(ddd, J=21.6, 14.3, 9.2 Hz, 3H), 3.07(s, 3H), 2.84-2.76(m, 1H), 2.64(dq, J=13.8, 6.9 Hz, 1H) | 150.28, 143.12, 141.04, 136.96, 135.43, 134.85, 133.47, 132.82, 130.58, 128.96, 128.61, 128.35, 127.88, 126.66, 126.16, 125.98, 125.19, 121.67, 121.04, 119.76, 117.66, 110.08, 109.61, 72.78, 43.74, 31.35 |
7i | 8.17(d, J=7.8 Hz, 1H), 7.92(s, 1H), 7.61(dd, J=19.8, 10.6 Hz, 3H), 7.42(d, J=8.3 Hz, 1H), 7.30(t, J=7.5 Hz, 1H), 7.06(d, J=8.5 Hz, 2H), 5.94(ddt, J=17.1, 10.1, 7.0 Hz, 1H), 5.14(dd, J=30.2, 13.6 Hz, 2H), 5.03(dd, J=7.3, 4.8 Hz, 1H), 3.91(s, 3H), 3.51(s, 3H), 2.80-2.74(m, 1H), 2.62(dt, J=14.4, 7.3 Hz, 1H) | 159.95, 150.06, 143.72, 142.20, 134.98, 134.63, 131.27, 131.03, 128.62, 121.60, 121.22, 119.83, 117.53, 113.62, 109.84, 109.47, 72.44, 55.42, 43.56, 33.01 |
7j | 8.18(d, J=7.8 Hz, 1H), 7.96(s, 1H), 7.66-7.58(m, 1H), 7.46-7.39(m, 2H), 7.30(dd, J=18.7, 11.3 Hz, 1H), 7.21(dd, J=8.0, 4.8 Hz, 2H), 7.05(dd, J=8.3, 2.1 Hz, 1H), 5.94(ddt, J=17.1, 10.1, 7.0 Hz, 1H), 5.14(dd, J=29.4, 13.7 Hz, 2H), 5.04(dd, J=7.4, 4.8 Hz, 1H), 3.89(s, 3H), 3.49(s, 3H), 2.81-2.74(m, 1H), 2.62(dt, J=14.4, 7.4 Hz, 1H) | 159.41, 150.07, 143.64, 142.15, 134.95, 134.48, 131.26, 129.16, 128.68, 122.35, 121.61, 121.14, 119.87, 117.61, 115.21, 114.36, 109.84, 109.82, 72.52, 55.42, 43.59, 32.89, 29.70 |
7k | 8.41(d, J=8.6 Hz, 2H), 8.19(d, J=7.8 Hz, 1H), 8.03(s, 1H), 7.89-7.86(m, 2H), 7.67-7.63(m, 1H), 7.45(d, J=8.3 Hz, 1H), 7.35(t, J=7.5 Hz, 1H), 5.92(ddt, J=17.2, 10.2, 7.0 Hz, 1H), 5.19-5.11(m, 2H), 5.05(dd, J=7.3, 4.8 Hz, 1H), 3.50(s, 3H), 2.81-2.75(m, 1H), 2.63(dt, J=14.4, 7.3 Hz, 1H) | 167.71, 150.86, 147.83, 146.02, 143.85, 139.34, 134.73, 134.58, 132.12, 130.79, 129.22, 123.42, 121.77, 121.13, 120.42, 117.95, 110.87, 109.98, 72.53, 43.50, 33.57 |
7l | 8.03(d, J=7.7 Hz, 1H), 7.64(s, 1H), 7.52(t, J=7.6 Hz, 1H), 7.37(d, J=8.3 Hz, 1H), 7.22-7.16(m, 2H), 5.83(ddt, J=17.1, 10.2, 7.0 Hz, 1H), 5.08-4.98(m, 2H), 4.90-4.85(m, 1H), 3.51-3.42(m, 1H), 2.67-2.59(m, 1H), 2.50(dt, J=13.8, 6.8 Hz, 1H), 1.99-1.83(m, 7H), 1.76(d, J=12.7 Hz, 1H), 1.46-1.41(m, 2H), 1.35-1.30(m, 1H) | 147.95, 147.27, 141.97, 134.02, 132.95, 129.55, 127.21, 120.29, 120.20, 118.44, 116.12, 108.41, 107.31, 70.98, 42.73, 41.04, 31.93, 31.88, 31.61, 28.68, 25.72, 25.14 |
Compd. | IC50/(μmol·L-1) | ||||
---|---|---|---|---|---|
HELA | MGC-803 | MCF-7 | A549 | SMMC-7721 | |
3a | 5.24±0.97 | - | - | 22.89±1.26 | - |
3b | - | - | - | 3.17±1.11 | - |
3d | - | - | 11.06±1.03 | - | - |
3f | 11.73±0.78 | 25.88±2.92 | 35.19±0.99 | 9.92±2.11 | - |
3g | 26.21±0.98 | - | - | - | - |
3h | 33.47±1.27 | - | - | - | - |
3l | 29.30±0.92 | - | - | - | - |
4c | - | - | - | 34.95±1.48 | - |
4d | 25.23±0.91 | - | - | - | - |
5f | 4.47±0.87 | 5.93±0.71 | 13.43±1.23 | 8.77±1.49 | 9.73±2.69 |
(R,S)-7g | 39.01±0.97 | - | - | - | - |
(R)-7h | 29.18±0.89 | - | - | - | - |
cis-platin | 5.98±0.26 | 10.06±0.54 | 5.486±0.74 | 1.45±0.59 | 11.07±1.26 |
Table 3 Inhibition activity of β-carboline compounds against five human cancer cell lines by MTT assay*
Compd. | IC50/(μmol·L-1) | ||||
---|---|---|---|---|---|
HELA | MGC-803 | MCF-7 | A549 | SMMC-7721 | |
3a | 5.24±0.97 | - | - | 22.89±1.26 | - |
3b | - | - | - | 3.17±1.11 | - |
3d | - | - | 11.06±1.03 | - | - |
3f | 11.73±0.78 | 25.88±2.92 | 35.19±0.99 | 9.92±2.11 | - |
3g | 26.21±0.98 | - | - | - | - |
3h | 33.47±1.27 | - | - | - | - |
3l | 29.30±0.92 | - | - | - | - |
4c | - | - | - | 34.95±1.48 | - |
4d | 25.23±0.91 | - | - | - | - |
5f | 4.47±0.87 | 5.93±0.71 | 13.43±1.23 | 8.77±1.49 | 9.73±2.69 |
(R,S)-7g | 39.01±0.97 | - | - | - | - |
(R)-7h | 29.18±0.89 | - | - | - | - |
cis-platin | 5.98±0.26 | 10.06±0.54 | 5.486±0.74 | 1.45±0.59 | 11.07±1.26 |
Compd. | MIC/(μmol·L-1) | ||||
---|---|---|---|---|---|
Micrococcus lysodeikticus | Bacillus subtilis | Staphyloccocus aureus | Vibrio anguillarum | Vibrio Parahemolyticus | |
4b | 6.25 | 3.13 | 12.50 | 6.25 | 3.13 |
4g | 25.00 | 12.50 | - | - | - |
5b | 25.00 | 25.00 | 25.00 | 12.50 | 25.00 |
5c | 25.00 | 6.25 | - | 12.50 | 25.00 |
5g | 12.50 | - | - | 6.25 | 25.00 |
5h | 12.50 | 6.25 | 25.00 | 0.78 | 3.13 |
5i | - | 12.50 | - | 6.25 | - |
5j | 25.00 | 6.25 | 25.00 | 6.25 | 25.00 |
6a | - | - | - | - | - |
6b | 12.50 | 1.56 | - | 25.00 | 12.50 |
6g | - | 12.50 | - | 25.00 | - |
6h | 25.00 | 6.25 | - | 25.00 | - |
(S)-7b | 25.00 | 6.25 | - | 12.50 | - |
(R)-7g | 12.50 | 6.25 | - | 12.50 | - |
(S)-7h | 6.25 | 1.56 | - | 12.50 | - |
Ciprofloxacin | 5.00 | 1.25 | 5.00 | 1.25 | 2.50 |
Table 4 Inhibition activity of β-carboline compounds against five bacterial strains*
Compd. | MIC/(μmol·L-1) | ||||
---|---|---|---|---|---|
Micrococcus lysodeikticus | Bacillus subtilis | Staphyloccocus aureus | Vibrio anguillarum | Vibrio Parahemolyticus | |
4b | 6.25 | 3.13 | 12.50 | 6.25 | 3.13 |
4g | 25.00 | 12.50 | - | - | - |
5b | 25.00 | 25.00 | 25.00 | 12.50 | 25.00 |
5c | 25.00 | 6.25 | - | 12.50 | 25.00 |
5g | 12.50 | - | - | 6.25 | 25.00 |
5h | 12.50 | 6.25 | 25.00 | 0.78 | 3.13 |
5i | - | 12.50 | - | 6.25 | - |
5j | 25.00 | 6.25 | 25.00 | 6.25 | 25.00 |
6a | - | - | - | - | - |
6b | 12.50 | 1.56 | - | 25.00 | 12.50 |
6g | - | 12.50 | - | 25.00 | - |
6h | 25.00 | 6.25 | - | 25.00 | - |
(S)-7b | 25.00 | 6.25 | - | 12.50 | - |
(R)-7g | 12.50 | 6.25 | - | 12.50 | - |
(S)-7h | 6.25 | 1.56 | - | 12.50 | - |
Ciprofloxacin | 5.00 | 1.25 | 5.00 | 1.25 | 2.50 |
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