高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (10): 2279.doi: 10.7503/cjcu20200529
• 研究论文 • 上一篇
收稿日期:
2020-08-03
出版日期:
2020-10-10
发布日期:
2020-10-08
通讯作者:
鲁桂
E-mail:lugui@mail.sysu.edu.cn
基金资助:
YOU Yipeng, NIE Lin, LIU Jinbiao, FENG Yahui, LU Gui()
Received:
2020-08-03
Online:
2020-10-10
Published:
2020-10-08
Contact:
LU Gui
E-mail:lugui@mail.sysu.edu.cn
Supported by:
摘要:
对上市药物扎那米韦、 奥司他韦和帕拉米韦进行结构修饰, 对化合物相应的氨基进行磷酰化, 设计合成了10个新化合物. 新化合物在酶水平和细胞水平均具有一定的抗流感病毒活性, 化合物I-8在酶水平、 化合物I-6在细胞水平具有和阳性对照药奥司他韦相当的活性.
中图分类号:
TrendMD:
尤义鹏, 聂林, 刘晋彪, 丰亚辉, 鲁桂. 新型神经氨酸酶抑制剂的设计合成及抗流感病毒活性. 高等学校化学学报, 2020, 41(10): 2279.
YOU Yipeng, NIE Lin, LIU Jinbiao, FENG Yahui, LU Gui. Design, Synthesis and Anti-influenza Activities of Novel Neuraminidase Inhibitors†. Chem. J. Chinese Universities, 2020, 41(10): 2279.
Compd. | Appearance | m.p./℃ | [α] | Yield(%) | HRMS(calcd.), m/z* |
---|---|---|---|---|---|
I?1 | White solid | 166.3—167.8 | +115.4 | 85 | 449.1296(449.1296) |
I?2 | White solid | 170.2—171.4 | +32.2 | 66 | 453.1649(453.1644) |
I?3 | White solid | 163.7—165.2 | +96.2 | 86 | 421.0998(421.0983) |
I?4 | White solid | 173.5—174.8 | +14.3 | 60 | 481.1966(481.1957) |
I?5 | White solid | 180.3—182.1 | +18.3 | 75 | 445.0976(445.1018) |
I?6 | White solid | 176.5—178.3 | -3.54 | 65 | 369.0366(369.0705) |
I?7 | White solid | 212.9—214.8 | -51.2 | 83 | 443.1914(443.1918) |
I?8 | White solid | 208.4—209.8 | -29.0 | 45 | 415.1594(415.1605) |
I?9 | White solid | 218.7—220.3 | -123.3 | 45 | 463.1589(463.1605) |
I?10 | White solid | 206.7—207.8 | -45.9 | 69 | 423.2251(423.2255) |
Table 1 Appearance, yields and HRMS data of compounds I-1—I-10
Compd. | Appearance | m.p./℃ | [α] | Yield(%) | HRMS(calcd.), m/z* |
---|---|---|---|---|---|
I?1 | White solid | 166.3—167.8 | +115.4 | 85 | 449.1296(449.1296) |
I?2 | White solid | 170.2—171.4 | +32.2 | 66 | 453.1649(453.1644) |
I?3 | White solid | 163.7—165.2 | +96.2 | 86 | 421.0998(421.0983) |
I?4 | White solid | 173.5—174.8 | +14.3 | 60 | 481.1966(481.1957) |
I?5 | White solid | 180.3—182.1 | +18.3 | 75 | 445.0976(445.1018) |
I?6 | White solid | 176.5—178.3 | -3.54 | 65 | 369.0366(369.0705) |
I?7 | White solid | 212.9—214.8 | -51.2 | 83 | 443.1914(443.1918) |
I?8 | White solid | 208.4—209.8 | -29.0 | 45 | 415.1594(415.1605) |
I?9 | White solid | 218.7—220.3 | -123.3 | 45 | 463.1589(463.1605) |
I?10 | White solid | 206.7—207.8 | -45.9 | 69 | 423.2251(423.2255) |
Compd. | 1H NMR(400 MHz), δ | 13C NMR(101 MHz), δ | 31P NMR(162 MHz), δ |
---|---|---|---|
I?1 | 5.86(d, J=1.9 Hz, 1H), 4.24(d, J=10.0 Hz, 1H), 4.02(m, 4H), 3.84(m, 3H), 3.61(t, J=8.1 Hz, 3H), 2.03(d, J=3.0 Hz, 3H), 1.27(dd, J=12.6, 6.0 Hz, 6H) | 174.6, 167.0, 147.1, 111.8, 78.3, 71.3, 70.2, 64.9, 64.0, 51.4, 50.8, 23.0, 16.5 | 10.04 |
I?2 | 6.00(s, 1H), 4.55(m, 2H), 4.29(d, J=10.0 Hz, 1H), 4.08(m, 2H), 3.89(dd, J=16.5, 8.0 Hz, 2H), 3.65(d, J=8.2 Hz, 2H), 2.07(s, 3H), 1.30(d, J=6.3 Hz, 12H) | 174.4, 165.8, 144.0, 112.9, 76.6, 73.3, 70.0, 68.2, 63.1, 50.4, 49.0, 23.0, 22.4 | 7.83 |
Compd. | 1H NMR(400 MHz), δ | 13C NMR(101 MHz), δ | 31P NMR(162 MHz), δ |
I?3 | 6.03(s, 1H), 4.34(d, J=9.4 Hz, 1H), 4.10(d, J=7.8 Hz, 2H), 3.92(m, 2H), 3.74(dd, J=21.6, 10.7 Hz, 8H), 2.10(s, 3H) | 174.5, 165.4, 143.8, 113.0, 76.5, 69.9, 68.0, 63.0, 53.9, 50.2, 49.0, 22.2 | 12.57 |
I?4 | 5.76(s, 1H), 4.17(d, J=10.0 Hz, 1H), 3.92(d, J=7.6 Hz, 6H), 3.80(m, 2H), 3.54(d, J=8.2 Hz, 2H), 1.97(s, 3H), 1.57(d, J=6.0 Hz, 4H), 1.30(s, 4H), 0.83(d, J=6.7 Hz, 6H) | 174.3, 167.1, 145.6, 110.8, 76.2, 69.8, 68.1, 67.5, 63.1, 50.3, 31.6, 22.2, 18.2, 12.8 | |
I?5 | 7.40(t, J=7.8 Hz, 2H), 7.21(m, 3H), 5.69(s, 1H), 4.36(m, 2H), 4.20(d, J=7.1 Hz, 1H), 3.96(dd, J=16.5, 7.9 Hz, 1H), 3.91(d, J=11.9 Hz, 1H), 3.68(m, 2H), 2.09(s, 3H) | 174.9, 168.5, 152.3, 150.7, 129.6, 123.7, 120.4, 99.9, 75.1, 69.7, 67.8, 63.0, 50.2, 45.9, 22.1 | -2.84 |
I?6 | 6.04(s, 1H), 4.46(d, J=6.0 Hz, 1H), 4.42(d, J=6.7 Hz, 1H), 4.33(d, J=5.9 Hz, 1H), 3.94(dd, J=21.2, 9.6 Hz, 2H), 3.75(d, J=9.2 Hz, 1H), 3.70(dd, J=11.6, 5.6 Hz, 1H), 2.11(d, J=5.7 Hz, 3H) | 175.0, 164.5, 146.3, 104.7, 75.8, 69.8, 67.6, 63.0, 49.8, 45.7, 22.3 | |
I?7 | 6.79(s, 1H), 4.11(m, 1H), 4.03(d, J=7.3 Hz, 4H), 3.86(dd, J=10.8, 8.5 Hz, 1H), 3.44(m, 1H), 3.27(m, 1H), 2.79(dd, J=17.8, 5.2 Hz, 1H), 2.30(m, 1H), 2.01(s, 3H), 1.50(m, 4H), 1.32(m, 6H), 0.92(dt, J=10.8, 7.4 Hz, 6H) | 174.0, 169.3, 138.9, 130.6, 83.7, 77.3, 64.3, 56.7, 52.0, 34.5, 27.3, 26.8, 23.3, 16.8, 16.4, 9.8 | 9.12 |
I?8 | 6.77(s, 1H), 4.10(d, J=8.6 Hz, 1H), 3.85(td, J=10.6, 6.3 Hz, 1H), 3.68(ddd, J=22.5, 10.0, 6.0 Hz, 6H), 3.40(m, 1H), 3.24(dd, J=13.3, 7.5 Hz, 1H), 2.79(dd, J=17.7, 5.3 Hz, 1H), 2.27(ddt, J=27.1, 22.6, 9.9 Hz, 1H), 2.00(s, 3H), 1.52(m, 4H), 0.91(dt, J=12.6, 7.4 Hz, 6H) | 174.1, 169.4, 139.0, 130.6, 83.7, 77.4, 56.9, 54.0, 52.1, 34.6, 27.0, 23.2, 9.7 | 11.74 |
I?9 | 7.40(t, J=7.8 Hz, 2H), 7.19(m, 3H), 6.38(s, 1H), 4.18(d, J=8.6 Hz, 1H), 3.77(m, 1H), 3.51(m, 1H), 3.26(qd, J=10.3, 5.3 Hz, 1H), 2.69(dd, J=17.5, 5.0 Hz, 1H), 2.22(m, 1H), 1.89(s, 3H), 1.49(m, 4H), 0.87(dt, J=25.4, 7.3 Hz, 6H) | 175.3, 174.8, 152.6, 131.8, 129.7, 123.6, 120.3, 83.9, 77.3, 56.4, 51.2, 35.2, 25.6, 25.3, 22.4, 8.6 | 3.50 |
I?10 | 7.34(d, J=9.6 Hz, 1H), 4.25(m, 1H), 4.02(m, 4H), 3.64(d, J=9.6 Hz, 1H), 3.50(s, 1H), 2.75(d, J=6.4 Hz, 1H), 2.44(dt, J=12.9, 8.4 Hz, 1H), 2.07(d, J=4.1 Hz, 1H), 1.99(d, J=12.1 Hz, 3H), 1.93(s, 1H), 1.58(m, 4H), 1.28(dd, J=11.9, 6.2 Hz, 6H), 0.81(dt, J=14.6, 7.3 Hz, 6H) | 177.4, 172.0, 63.1, 52.2, 52.1, 49.7, 48.8, 43.7, 35.6, 22.9, 22.0, 21.3, 16.2, 10.6 | 8.43 |
Table 2 1H NMR, 13C NMR and 31P NMR data of compounds I?1—I?10*
Compd. | 1H NMR(400 MHz), δ | 13C NMR(101 MHz), δ | 31P NMR(162 MHz), δ |
---|---|---|---|
I?1 | 5.86(d, J=1.9 Hz, 1H), 4.24(d, J=10.0 Hz, 1H), 4.02(m, 4H), 3.84(m, 3H), 3.61(t, J=8.1 Hz, 3H), 2.03(d, J=3.0 Hz, 3H), 1.27(dd, J=12.6, 6.0 Hz, 6H) | 174.6, 167.0, 147.1, 111.8, 78.3, 71.3, 70.2, 64.9, 64.0, 51.4, 50.8, 23.0, 16.5 | 10.04 |
I?2 | 6.00(s, 1H), 4.55(m, 2H), 4.29(d, J=10.0 Hz, 1H), 4.08(m, 2H), 3.89(dd, J=16.5, 8.0 Hz, 2H), 3.65(d, J=8.2 Hz, 2H), 2.07(s, 3H), 1.30(d, J=6.3 Hz, 12H) | 174.4, 165.8, 144.0, 112.9, 76.6, 73.3, 70.0, 68.2, 63.1, 50.4, 49.0, 23.0, 22.4 | 7.83 |
Compd. | 1H NMR(400 MHz), δ | 13C NMR(101 MHz), δ | 31P NMR(162 MHz), δ |
I?3 | 6.03(s, 1H), 4.34(d, J=9.4 Hz, 1H), 4.10(d, J=7.8 Hz, 2H), 3.92(m, 2H), 3.74(dd, J=21.6, 10.7 Hz, 8H), 2.10(s, 3H) | 174.5, 165.4, 143.8, 113.0, 76.5, 69.9, 68.0, 63.0, 53.9, 50.2, 49.0, 22.2 | 12.57 |
I?4 | 5.76(s, 1H), 4.17(d, J=10.0 Hz, 1H), 3.92(d, J=7.6 Hz, 6H), 3.80(m, 2H), 3.54(d, J=8.2 Hz, 2H), 1.97(s, 3H), 1.57(d, J=6.0 Hz, 4H), 1.30(s, 4H), 0.83(d, J=6.7 Hz, 6H) | 174.3, 167.1, 145.6, 110.8, 76.2, 69.8, 68.1, 67.5, 63.1, 50.3, 31.6, 22.2, 18.2, 12.8 | |
I?5 | 7.40(t, J=7.8 Hz, 2H), 7.21(m, 3H), 5.69(s, 1H), 4.36(m, 2H), 4.20(d, J=7.1 Hz, 1H), 3.96(dd, J=16.5, 7.9 Hz, 1H), 3.91(d, J=11.9 Hz, 1H), 3.68(m, 2H), 2.09(s, 3H) | 174.9, 168.5, 152.3, 150.7, 129.6, 123.7, 120.4, 99.9, 75.1, 69.7, 67.8, 63.0, 50.2, 45.9, 22.1 | -2.84 |
I?6 | 6.04(s, 1H), 4.46(d, J=6.0 Hz, 1H), 4.42(d, J=6.7 Hz, 1H), 4.33(d, J=5.9 Hz, 1H), 3.94(dd, J=21.2, 9.6 Hz, 2H), 3.75(d, J=9.2 Hz, 1H), 3.70(dd, J=11.6, 5.6 Hz, 1H), 2.11(d, J=5.7 Hz, 3H) | 175.0, 164.5, 146.3, 104.7, 75.8, 69.8, 67.6, 63.0, 49.8, 45.7, 22.3 | |
I?7 | 6.79(s, 1H), 4.11(m, 1H), 4.03(d, J=7.3 Hz, 4H), 3.86(dd, J=10.8, 8.5 Hz, 1H), 3.44(m, 1H), 3.27(m, 1H), 2.79(dd, J=17.8, 5.2 Hz, 1H), 2.30(m, 1H), 2.01(s, 3H), 1.50(m, 4H), 1.32(m, 6H), 0.92(dt, J=10.8, 7.4 Hz, 6H) | 174.0, 169.3, 138.9, 130.6, 83.7, 77.3, 64.3, 56.7, 52.0, 34.5, 27.3, 26.8, 23.3, 16.8, 16.4, 9.8 | 9.12 |
I?8 | 6.77(s, 1H), 4.10(d, J=8.6 Hz, 1H), 3.85(td, J=10.6, 6.3 Hz, 1H), 3.68(ddd, J=22.5, 10.0, 6.0 Hz, 6H), 3.40(m, 1H), 3.24(dd, J=13.3, 7.5 Hz, 1H), 2.79(dd, J=17.7, 5.3 Hz, 1H), 2.27(ddt, J=27.1, 22.6, 9.9 Hz, 1H), 2.00(s, 3H), 1.52(m, 4H), 0.91(dt, J=12.6, 7.4 Hz, 6H) | 174.1, 169.4, 139.0, 130.6, 83.7, 77.4, 56.9, 54.0, 52.1, 34.6, 27.0, 23.2, 9.7 | 11.74 |
I?9 | 7.40(t, J=7.8 Hz, 2H), 7.19(m, 3H), 6.38(s, 1H), 4.18(d, J=8.6 Hz, 1H), 3.77(m, 1H), 3.51(m, 1H), 3.26(qd, J=10.3, 5.3 Hz, 1H), 2.69(dd, J=17.5, 5.0 Hz, 1H), 2.22(m, 1H), 1.89(s, 3H), 1.49(m, 4H), 0.87(dt, J=25.4, 7.3 Hz, 6H) | 175.3, 174.8, 152.6, 131.8, 129.7, 123.6, 120.3, 83.9, 77.3, 56.4, 51.2, 35.2, 25.6, 25.3, 22.4, 8.6 | 3.50 |
I?10 | 7.34(d, J=9.6 Hz, 1H), 4.25(m, 1H), 4.02(m, 4H), 3.64(d, J=9.6 Hz, 1H), 3.50(s, 1H), 2.75(d, J=6.4 Hz, 1H), 2.44(dt, J=12.9, 8.4 Hz, 1H), 2.07(d, J=4.1 Hz, 1H), 1.99(d, J=12.1 Hz, 3H), 1.93(s, 1H), 1.58(m, 4H), 1.28(dd, J=11.9, 6.2 Hz, 6H), 0.81(dt, J=14.6, 7.3 Hz, 6H) | 177.4, 172.0, 63.1, 52.2, 52.1, 49.7, 48.8, 43.7, 35.6, 22.9, 22.0, 21.3, 16.2, 10.6 | 8.43 |
Entry | Compd. | IC50 of NAs/(μmol·L-1) | IC50 of NAr/(μmol·L-1) |
---|---|---|---|
1 | I?1 | 4.14 | 95.4 |
2 | I?2 | 10.9 | 18.7 |
3 | I?3 | 3.15 | 2.86 |
4 | I?4 | 25.1 | 32.3 |
5 | I?5 | 0.1178 | 0.0757 |
6 | I?6 | 0.3558 | 0.259 |
7 | I?7 | 0.092 | 55.7 |
8 | I?8 | 0.000397 | 7.83 |
9 | I?9 | 0.239 | 151 |
10 | I?10 | 0.1947 | — |
11 | Oseltamivir | 0.000291 | 0.0794 |
12 | 4?Amino?DANA | 0.286 | 0.164 |
Table 3 Inhibition activities against NAs and NAr enzymes
Entry | Compd. | IC50 of NAs/(μmol·L-1) | IC50 of NAr/(μmol·L-1) |
---|---|---|---|
1 | I?1 | 4.14 | 95.4 |
2 | I?2 | 10.9 | 18.7 |
3 | I?3 | 3.15 | 2.86 |
4 | I?4 | 25.1 | 32.3 |
5 | I?5 | 0.1178 | 0.0757 |
6 | I?6 | 0.3558 | 0.259 |
7 | I?7 | 0.092 | 55.7 |
8 | I?8 | 0.000397 | 7.83 |
9 | I?9 | 0.239 | 151 |
10 | I?10 | 0.1947 | — |
11 | Oseltamivir | 0.000291 | 0.0794 |
12 | 4?Amino?DANA | 0.286 | 0.164 |
Entry | Compd. | IC50/(μmol·L-1) | |
---|---|---|---|
H3N2 | H1N1 | ||
1 | I?1 | 125 | 54.5 |
2 | I?3 | 3.15 | 10.92 |
3 | I?5 | 0.149 | 0.292 |
4 | I?6 | 0.121 | 0.798 |
5 | I?7 | 3.23 | 6.06 |
6 | I?8 | 6.73 | 25.9 |
7 | I?9 | 0.315 | 9.94 |
8 | I?10 | 0.619 | 4.629 |
9 | Oseltamivir | 0.0851 | 0.025 |
10 | 4?Amino?DANA | 1.23 | 2.3 |
Table 4 In vitro anti-influenza virus activities in MDCK cells using the CPE protection assay
Entry | Compd. | IC50/(μmol·L-1) | |
---|---|---|---|
H3N2 | H1N1 | ||
1 | I?1 | 125 | 54.5 |
2 | I?3 | 3.15 | 10.92 |
3 | I?5 | 0.149 | 0.292 |
4 | I?6 | 0.121 | 0.798 |
5 | I?7 | 3.23 | 6.06 |
6 | I?8 | 6.73 | 25.9 |
7 | I?9 | 0.315 | 9.94 |
8 | I?10 | 0.619 | 4.629 |
9 | Oseltamivir | 0.0851 | 0.025 |
10 | 4?Amino?DANA | 1.23 | 2.3 |
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