高等学校化学学报 ›› 2017, Vol. 38 ›› Issue (3): 392.doi: 10.7503/cjcu20160880
收稿日期:
2016-12-06
出版日期:
2017-03-10
发布日期:
2017-02-23
作者简介:
联系人简介: 刘玉明, 男, 博士, 副教授, 主要从事药物化学和天然药物化学研究. E-mail: 基金资助:
LIU Yuming*(), TIAN Lijun, HU Dong, NIE Jianbing
Received:
2016-12-06
Online:
2017-03-10
Published:
2017-02-23
Contact:
LIU Yuming
E-mail:liuyuming@tjut.edu.cn
Supported by:
摘要:
设计合成了一系列4-N-苯胺基喹啉类衍生物, 采用Ellman法测定了目标化合物对乙酰胆碱酯酶(AChE)和丁酰胆碱酯酶(BChE)的抑制活性. 结果表明, 当喹啉环上连有伸长的吡啶季铵盐片段时, 可显著提高目标化合物的胆碱酯酶抑制作用. 化合物16对AChE和BChE具有明显的双重抑制作用, 其IC50值分别为0.92和14.20 μmol/L, 抑制效果强于阳性对照药加兰他敏.
中图分类号:
TrendMD:
刘玉明, 田丽珺, 胡栋, 聂建兵. 4-N-苯胺基喹啉衍生物的合成及胆碱酯酶抑制活性. 高等学校化学学报, 2017, 38(3): 392.
LIU Yuming, TIAN Lijun, HU Dong, NIE Jianbing. yntheses and Anti-cholinesterase Activity of 4-N-Phenylaminoquinoline Derivatives †. Chem. J. Chinese Universities, 2017, 38(3): 392.
Compd. | Appearance | Yield(%) | m. p./℃ | HR-ESI-MS(Calcd.), m/z |
---|---|---|---|---|
6a | Yellow solid | 82.3 | 274—276(274—276[ | 255.0743(255.0689)[M+H]+ |
6b | Yellow solid | 86.4 | 280—283(279—281[ | 269.0888(269.0846)[M+H]+ |
6c | Slightly yellow solid | 78.0 | 297—299(298—299[ | 271.0679(271.0638)[M+H]+ |
6d | Slightly yellow solid | 75.1 | >300(303—305[ | 271.0683(271.0638)[M+H]+ |
6e | White solid | 56.1 | 241—243(241—243[ | 289.0342(289.0299)[M+H]+ |
6f | White solid | 80.9 | 261—263(261—262[ | 289.0343(289.0299)[M+H]+ |
6g | Slightly yellow solid | 75.2 | 292—294(292—293[ | 289.0320(289.0299)[M+H]+ |
6h | White solid | 50.2 | >300 | 322.9936(322.9910)[M+H]+ |
6i | White solid | 43.4 | >300 | 319.0454(319.0405)[M+H]+ |
6j | White solid | 42.9 | >300 | 353.0038(353.0015)[M+H]+ |
7 | White solid | 88.4 | 61—63(63—64[ | 181.0505(181.0501)[M-H]- |
8 | White solid | 79.2 | 100—102(99—100[ | |
9 | Yellow solid | 86.2 | 65—67(66—68[ | 326.0403(326.0407)[M+Na]+ |
10 | White solid | 87.4 | 98—99(97—98[ | 274.0858(274.0846)[M+H]+ |
11 | White solid | 82.0 | 165—166(164—165[ | 258.0535(258.0533)[M-H]- |
12 | Yellow solid | 83.1 | 184—186 | 329.0545(329.0540)[M-H]- |
13 | Grey-white solid | 30.9 | 270—272 | 313.0594(313.0591)[M+H]+ |
14 | Grey-white solid | 88.6 | 121—123 | 331.0260(331.0252)[M+H]+ |
15 | Yellow solid | 74.5 | 169—171 | 422.0691(422.0674)[M+H]+ |
16 | Red solid | 66.7 | 229—232 | 465.1364(465.1330)[M-Cl]+ |
17 | Yellow solid | 77.8 | 163—165 | 435.1586(435.1588)[M-Cl]+ |
Table 1 Appearance, yield, melting points and HRMS data of compounds 6—17
Compd. | Appearance | Yield(%) | m. p./℃ | HR-ESI-MS(Calcd.), m/z |
---|---|---|---|---|
6a | Yellow solid | 82.3 | 274—276(274—276[ | 255.0743(255.0689)[M+H]+ |
6b | Yellow solid | 86.4 | 280—283(279—281[ | 269.0888(269.0846)[M+H]+ |
6c | Slightly yellow solid | 78.0 | 297—299(298—299[ | 271.0679(271.0638)[M+H]+ |
6d | Slightly yellow solid | 75.1 | >300(303—305[ | 271.0683(271.0638)[M+H]+ |
6e | White solid | 56.1 | 241—243(241—243[ | 289.0342(289.0299)[M+H]+ |
6f | White solid | 80.9 | 261—263(261—262[ | 289.0343(289.0299)[M+H]+ |
6g | Slightly yellow solid | 75.2 | 292—294(292—293[ | 289.0320(289.0299)[M+H]+ |
6h | White solid | 50.2 | >300 | 322.9936(322.9910)[M+H]+ |
6i | White solid | 43.4 | >300 | 319.0454(319.0405)[M+H]+ |
6j | White solid | 42.9 | >300 | 353.0038(353.0015)[M+H]+ |
7 | White solid | 88.4 | 61—63(63—64[ | 181.0505(181.0501)[M-H]- |
8 | White solid | 79.2 | 100—102(99—100[ | |
9 | Yellow solid | 86.2 | 65—67(66—68[ | 326.0403(326.0407)[M+Na]+ |
10 | White solid | 87.4 | 98—99(97—98[ | 274.0858(274.0846)[M+H]+ |
11 | White solid | 82.0 | 165—166(164—165[ | 258.0535(258.0533)[M-H]- |
12 | Yellow solid | 83.1 | 184—186 | 329.0545(329.0540)[M-H]- |
13 | Grey-white solid | 30.9 | 270—272 | 313.0594(313.0591)[M+H]+ |
14 | Grey-white solid | 88.6 | 121—123 | 331.0260(331.0252)[M+H]+ |
15 | Yellow solid | 74.5 | 169—171 | 422.0691(422.0674)[M+H]+ |
16 | Red solid | 66.7 | 229—232 | 465.1364(465.1330)[M-Cl]+ |
17 | Yellow solid | 77.8 | 163—165 | 435.1586(435.1588)[M-Cl]+ |
Compd. | 1H NMR(400 MHz), δ | 13C NMR(100 MHz), δ | |
---|---|---|---|
6h | 6.50(d, J=6.9 Hz, 1H), 7.59(br s, 2H), 7.79(br s, 1H), 7.83(dd, J=2.0, 9.1 Hz, 1H), 8.04(d, J=2.0 Hz, 1H), 8.46(d, J=6.9 Hz, 1H), 8.61(d, J=9.1 Hz, 1H) | 103.2, 118.1, 118.6, 121.8, 127.2, 130.5, 131.3, 132.7, 132.9, 135.2, 137.4, 141.6, 142.6, 145.7, 158.5 | |
6i | 3.80(s, 3H), 6.34(d, J=6.9 Hz, 1H), 7.12(dd, J=3.0, 9.0 Hz, 1H), 7.22(d, J=3.0 Hz, 1H), 7.62(d, J=9.0 Hz, 1H), 7.88(dd, J=2.0, 9.1 Hz, 1H), 8.28(d, J=2.0 Hz, 1H), 8.57(d, J=6.9 Hz, 1H), 8.99(d, J=9.1 Hz, 1H), 11.46(br s, 1H, NH) | 56.4, 101.4, 115.4, 116.0, 116.4, 119.7, 122.5, 126.7, 128.1, 131.7, 135.2, 139.0, 139.4, 143.8, 155.7, 159.7 | |
6j | 3.85(s, 3H), 6.28(br s, 1H), 7.26(s, 1H), 7.61(d, J=8.5 Hz, 1H), 7.77(s, 1H), 7.91(br s, 1H), 8.42(br s, 1H), 8.47(d, J=8.5 Hz, 1H) | 57.2, 102.8, 112.9, 118.2, 119.9, 122.0, 125.2, 125.9, 126.5, 131.0, 135.1, 137.6, 148.0, 150.0, 150.6, 154.9 | |
12 | 2.21(m, 2H), 3.78(s, 3H), 3.79(t, J=6.4 Hz, 2H), 4.22(t, J=5.9 Hz, 2H), 6.66(d, J=6.1 Hz, 1H), 7.25(s, 1H), 7.53(s, 1H), 8.02(dd, J=6.1, 13.2 Hz, 1H), 13.93(d, J=13.2 Hz, 1H) | 31.6, 41.9, 55.9, 65.7, 100.2, 108.4, 112.7, 113.4, 136.2, 138.2, 144.9, 153.1, 168.1 | |
13 | 2.27(m, 2H), 3.82(t, J=6.4 Hz, 2H), 3.90(s, 3H), 4.21(t, J=6.1 Hz, 2H), 7.19(s, 1H), 7.60(s, 1H), 9.08(s, 1H) | 31.4, 41.8, 55.8, 65.5, 101.9, 105.4, 122.2, 130.4, 134.5, 140.7, 148.1, 152.4, 166.6 | |
14 | 2.29(m, 2H), 3.83(t, J=6.4 Hz, 2H), 4.02(s, 3H), 4.36(t, J=5.9 Hz, 2H), 7.52(s, 1H), 7.58(s, 1H), 9.17(s, 1H) | 31.4, 41.8, 56.3, 65.9, 102.9, 109.0, 120.4, 132.6, 139.8, 142.7, 146.4, 152.1, 154.2 | |
15 | 2.26(m, 2H), 3.78( s, 3H), 3.81(t, J=6.4 Hz, 2H), 4.28(t, J=5.8 Hz, 2H), 7.08(d, J=8.6 Hz, 2H), 7.36(d, J=8.6 Hz, 2H), 7.39(s, 1H), 7.56(s, 1H), 8.94(s, 1H), 9.80(s, 1H, NH) | 31.9, 42.3, 56.3, 65.8, 104.1, 109.9, 115.4, 122.0(2C), 128.0, 129.5(2C), 130.3, 141.0, 141.2, 144.9, 146.9, 149.7, 153.3 | |
16 | 2.56(m, 2H), 3.73( s, 3H), 4.36(t, J=5.4 Hz, 2H), 4.86(t, J=6.2 Hz, 2H), 7.10(d, J=8.6 Hz, 2H), 7.34(d, J=8.6 Hz, 2H), 7.38(s, 1H), 7.78(s, 1H), 8.14(t-like, J=6.9 Hz, 2H), 8.63(t, J=7.8 Hz, 1H), 8.92(s, 1H), 9.17(d, J=5.8 Hz, 2H), 10.12(s, 1H, NH) | 30.0, 56.5, 59.7, 66.9, 104.4, 109.8, 115.9, 121.5(2C), 127.6, 128.4(2C), 129.4(2C), 130.3, 140.9, 141.2, 145.0, 145.5(2C), 145.8, 146.8, 149.5, 152.8 | |
17 | 2.69(m, 2H), 3.68( s, 3H), 4.40(t, J=5.4 Hz, 2H), 4.97(t, J=6.6 Hz, 2H), 6.97(d, J=8.0 Hz, 2H), 7.17(s, 1H), 7.32(s, 1H),7.34(d, J=8.0 Hz, 2H), 8.14(t-like, J=6.6 Hz, 2H), 8.31(s, 1H), 8.65(t, J=7.7 Hz, 1H), 9.14(d, J=5.6 Hz, 2H) | 29.8, 54.8, 59.7, 66.4, 101.2, 102.4, 118.6, 119.5(2C), 126.4, 128.0, 128.1(2C), 128.6(2C), 130.0, 131.1, 132.7, 140.5, 145.0(2C), 145.4, 150.1, 150.5 |
Table 2 1H NMR and 13C NMR data of compounds 6h—6j and 12—17*
Compd. | 1H NMR(400 MHz), δ | 13C NMR(100 MHz), δ | |
---|---|---|---|
6h | 6.50(d, J=6.9 Hz, 1H), 7.59(br s, 2H), 7.79(br s, 1H), 7.83(dd, J=2.0, 9.1 Hz, 1H), 8.04(d, J=2.0 Hz, 1H), 8.46(d, J=6.9 Hz, 1H), 8.61(d, J=9.1 Hz, 1H) | 103.2, 118.1, 118.6, 121.8, 127.2, 130.5, 131.3, 132.7, 132.9, 135.2, 137.4, 141.6, 142.6, 145.7, 158.5 | |
6i | 3.80(s, 3H), 6.34(d, J=6.9 Hz, 1H), 7.12(dd, J=3.0, 9.0 Hz, 1H), 7.22(d, J=3.0 Hz, 1H), 7.62(d, J=9.0 Hz, 1H), 7.88(dd, J=2.0, 9.1 Hz, 1H), 8.28(d, J=2.0 Hz, 1H), 8.57(d, J=6.9 Hz, 1H), 8.99(d, J=9.1 Hz, 1H), 11.46(br s, 1H, NH) | 56.4, 101.4, 115.4, 116.0, 116.4, 119.7, 122.5, 126.7, 128.1, 131.7, 135.2, 139.0, 139.4, 143.8, 155.7, 159.7 | |
6j | 3.85(s, 3H), 6.28(br s, 1H), 7.26(s, 1H), 7.61(d, J=8.5 Hz, 1H), 7.77(s, 1H), 7.91(br s, 1H), 8.42(br s, 1H), 8.47(d, J=8.5 Hz, 1H) | 57.2, 102.8, 112.9, 118.2, 119.9, 122.0, 125.2, 125.9, 126.5, 131.0, 135.1, 137.6, 148.0, 150.0, 150.6, 154.9 | |
12 | 2.21(m, 2H), 3.78(s, 3H), 3.79(t, J=6.4 Hz, 2H), 4.22(t, J=5.9 Hz, 2H), 6.66(d, J=6.1 Hz, 1H), 7.25(s, 1H), 7.53(s, 1H), 8.02(dd, J=6.1, 13.2 Hz, 1H), 13.93(d, J=13.2 Hz, 1H) | 31.6, 41.9, 55.9, 65.7, 100.2, 108.4, 112.7, 113.4, 136.2, 138.2, 144.9, 153.1, 168.1 | |
13 | 2.27(m, 2H), 3.82(t, J=6.4 Hz, 2H), 3.90(s, 3H), 4.21(t, J=6.1 Hz, 2H), 7.19(s, 1H), 7.60(s, 1H), 9.08(s, 1H) | 31.4, 41.8, 55.8, 65.5, 101.9, 105.4, 122.2, 130.4, 134.5, 140.7, 148.1, 152.4, 166.6 | |
14 | 2.29(m, 2H), 3.83(t, J=6.4 Hz, 2H), 4.02(s, 3H), 4.36(t, J=5.9 Hz, 2H), 7.52(s, 1H), 7.58(s, 1H), 9.17(s, 1H) | 31.4, 41.8, 56.3, 65.9, 102.9, 109.0, 120.4, 132.6, 139.8, 142.7, 146.4, 152.1, 154.2 | |
15 | 2.26(m, 2H), 3.78( s, 3H), 3.81(t, J=6.4 Hz, 2H), 4.28(t, J=5.8 Hz, 2H), 7.08(d, J=8.6 Hz, 2H), 7.36(d, J=8.6 Hz, 2H), 7.39(s, 1H), 7.56(s, 1H), 8.94(s, 1H), 9.80(s, 1H, NH) | 31.9, 42.3, 56.3, 65.8, 104.1, 109.9, 115.4, 122.0(2C), 128.0, 129.5(2C), 130.3, 141.0, 141.2, 144.9, 146.9, 149.7, 153.3 | |
16 | 2.56(m, 2H), 3.73( s, 3H), 4.36(t, J=5.4 Hz, 2H), 4.86(t, J=6.2 Hz, 2H), 7.10(d, J=8.6 Hz, 2H), 7.34(d, J=8.6 Hz, 2H), 7.38(s, 1H), 7.78(s, 1H), 8.14(t-like, J=6.9 Hz, 2H), 8.63(t, J=7.8 Hz, 1H), 8.92(s, 1H), 9.17(d, J=5.8 Hz, 2H), 10.12(s, 1H, NH) | 30.0, 56.5, 59.7, 66.9, 104.4, 109.8, 115.9, 121.5(2C), 127.6, 128.4(2C), 129.4(2C), 130.3, 140.9, 141.2, 145.0, 145.5(2C), 145.8, 146.8, 149.5, 152.8 | |
17 | 2.69(m, 2H), 3.68( s, 3H), 4.40(t, J=5.4 Hz, 2H), 4.97(t, J=6.6 Hz, 2H), 6.97(d, J=8.0 Hz, 2H), 7.17(s, 1H), 7.32(s, 1H),7.34(d, J=8.0 Hz, 2H), 8.14(t-like, J=6.6 Hz, 2H), 8.31(s, 1H), 8.65(t, J=7.7 Hz, 1H), 9.14(d, J=5.6 Hz, 2H) | 29.8, 54.8, 59.7, 66.4, 101.2, 102.4, 118.6, 119.5(2C), 126.4, 128.0, 128.1(2C), 128.6(2C), 130.0, 131.1, 132.7, 140.5, 145.0(2C), 145.4, 150.1, 150.5 |
Compd. | IC50/(μmol·L-1) | Compd. | IC50/(μmol·L-1) | ||
---|---|---|---|---|---|
AChE | BChE | AChE | BChE | ||
6a | 75.31±0.85 | >150 | 6h | 121.50±2.13 | >150 |
6b | 121.72±0.06 | >150 | 6i | >150 | >150 |
6c | 111.22±2.39 | >150 | 6j | 109.68±1.67 | >150 |
6d | 94.14±0.52 | >150 | 15 | 140.91±1.03 | >150 |
6e | 116.43±0.34 | 142.08±0.68 | 16 | 0.92±0.05 | 14.20±0.96 |
6f | 120.29±1.43 | >150 | 17 | 3.19±0.22 | 17.43±0.57 |
6g | 136.23±1.45 | >150 | Galanthamine | 2.30±0.03 | 20.47±1.92 |
Table 3 Inhibitory activity of target compounds on cholinesterase
Compd. | IC50/(μmol·L-1) | Compd. | IC50/(μmol·L-1) | ||
---|---|---|---|---|---|
AChE | BChE | AChE | BChE | ||
6a | 75.31±0.85 | >150 | 6h | 121.50±2.13 | >150 |
6b | 121.72±0.06 | >150 | 6i | >150 | >150 |
6c | 111.22±2.39 | >150 | 6j | 109.68±1.67 | >150 |
6d | 94.14±0.52 | >150 | 15 | 140.91±1.03 | >150 |
6e | 116.43±0.34 | 142.08±0.68 | 16 | 0.92±0.05 | 14.20±0.96 |
6f | 120.29±1.43 | >150 | 17 | 3.19±0.22 | 17.43±0.57 |
6g | 136.23±1.45 | >150 | Galanthamine | 2.30±0.03 | 20.47±1.92 |
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