高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (7): 1455.doi: 10.7503/cjcu20170785
张菊平, 李普, 王一会, 张橙, 陈丽娟, 汤旭, 贺鸣, 薛伟()
收稿日期:
2017-12-01
出版日期:
2018-07-10
发布日期:
2018-04-17
作者简介:
联系人简介: 薛 伟, 男, 博士, 教授, 博士生导师, 主要从事新农药和医药的创制研究. E-mail:基金资助:
ZHANG Juping, LI Pu, WANG Yihui, ZHANG Cheng, CHEN Lijuan, TANG Xu, HE Ming, XUE Wei*()
Received:
2017-12-01
Online:
2018-07-10
Published:
2018-04-17
Contact:
XUE Wei
E-mail:wxue@gzu.edu.cn
Supported by:
摘要:
为了得到生物活性较好的姜黄素衍生物, 通过1-苯基-5-取代基-1,4-戊二烯-3-酮和3-氯甲基苯并三嗪酮反应, 合成了14个含苯并三嗪酮的1,4-戊二烯-3-酮衍生物; 采用核磁共振波谱(NMR)和高分辨质谱(HRMS)对化合物的结构进行了表征. 初步的生物活性测试结果表明, 部分化合物显示出较好的抑菌活性, 在100 μg/mL剂量下, 化合物6b, 6j和6l对柑橘溃疡病菌(Xac)的抑制率分别为68.8%, 71.0%和100%; 化合物6a, 6d, 6h和6i对烟草青枯病菌(R. solanacearum)的抑制率分别为51.8%, 53.0%, 50.7%和76.9%. 此外, 化合物6l和6i对柑橘溃疡病菌和烟草青枯病菌的半最大效应浓度(EC50)值分别为27.44和48.77 μg/mL, 优于对照药剂噻菌铜(51.35和87.26 μg/mL), 有望成为柑橘溃疡病菌和烟草青枯病菌的抑制剂.
中图分类号:
TrendMD:
张菊平, 李普, 王一会, 张橙, 陈丽娟, 汤旭, 贺鸣, 薛伟. 含苯并三嗪酮的1,4-戊二烯-3-酮衍生物的合成及抑菌活性. 高等学校化学学报, 2018, 39(7): 1455.
ZHANG Juping, LI Pu, WANG Yihui, ZHANG Cheng, CHEN Lijuan, TANG Xu, HE Ming, XUE Wei. Synthesis and Antibacterial Activities of Penta-1,4-dien-3-one Derivatives Containing a Benzotriazin-4(3H)-one Moiety†. Chem. J. Chinese Universities, 2018, 39(7): 1455.
Compd. | 1H NMR(400 MHz, CDCl3), δ |
---|---|
2a | 7.85(dd, J=15.5, 4.4 Hz, 1H), 7.66(d, J=15.9 Hz, 1H), 7.36(dd, J=31.4, 4.2 Hz, 2H), 7.16(dd, J=8.2, 1.6 Hz, 1H), 7.11—7.05(m, 2H), 6.94(t, J=6.3 Hz, 1H), 6.87(dt, J=13.3, 6.5 Hz, 2H), 6.19(s, 1H), 3.93(s, 3H) |
2b | 7.69(t, J=17.0 Hz, 2H), 7.50(d, J=7.9 Hz, 2H), 7.18(dd, J=20.1, 8.1 Hz, 3H), 7.11—7.00(m, 2H), 6.93(t, J=12.5 Hz, 2H), 3.93(s, 3H), 2.37(s, 3H) |
2c | 8.84(d, J=2.0 Hz, 1H), 8.62(dd, J=4.8, 1.5 Hz, 1H), 7.93(dt, J=8.0, 1.8 Hz, 1H), 7.75—7.67(m, 2H), 7.37(dd, J=7.9, 4.8 Hz, 1H), 7.17(ddd, J=20.9, 7.4, 1.8 Hz, 3H), 6.95(dd, J=9.5, 6.4 Hz, 2H), 6.90(s, 1H), 3.96(s, 3H) |
2d | 8.51(s, 1H), 7.84(d, J=23.6 Hz, 2H), 7.48(s, 1H), 7.40(t, J=5.0 Hz, 3H), 7.20(s, 1H), 7.08(s, 1H), 6.98(s, 1H), 6.37(s, 1H), 4.91(s, 1H), 3.83(s, 3H) |
2f | 8.07(d, J=16.1 Hz, 1H), 7.67(d, J=15.8 Hz, 1H), 7.60(dd, J=7.7, 1.4 Hz, 1H), 7.40—7.32(m, 1H), 7.18—7.08(m, 3H), 7.00—6.89(m, 4H), 6.33(s, 1H), 3.92(s, 3H), 3.89(s, 3H) |
2h | 7.99(d, J=15.7 Hz, 1H), 7.59(dd, J=55.5, 11.6 Hz, 2H), 7.17—7.02(m, 3H), 6.93(d, J=8.9 Hz, 2H), 6.55—6.39(m, 2H), 6.21(s, 1H), 3.92(s, 3H), 3.87(s, 3H), 3.83(s, 3H) |
2i | 7.65(dd, J=16.2, 5.1 Hz, 2H), 7.54(dt, J=10.4, 5.2 Hz, 2H), 7.12(t, J=6.6 Hz, 1H), 7.09—7.02(m, 3H), 7.01—6.96(m, 1H), 6.93(dt, J=8.2, 2.1 Hz, 1H), 6.88(dt, J=15.7, 2.4 Hz, 1H), 6.45(s, 1H), 3.89(s, 3H) |
Compd. | 1H NMR(400 MHz, CDCl3), δ |
2j | 7.82—7.52(m, 3H), 7.40(s, 1H), 7.36(d, J=10.0 Hz, 2H), 7.20(s, 1H), 7.08(s, 1H), 6.93(s, 1H), 6.77(s, 1H), 5.05(s, 1H), 3.87(s, 3H), 3.85(s, 3H), 3.83(s, 3H) |
2k | 7.85—7.65(m, 3H), 7.64—7.55(m, 2H), 7.39(dd, J=9.9, 7.4 Hz, 3H), 7.22—7.05(m, 3H), 7.00—6.87(m, 2H), 3.92(s, 3H) |
2l | 8.44(s, 1H), 8.20(d, J=8.1 Hz, 1H), 7.85(d, J=7.6 Hz, 1H), 7.79—7.65(m, 2H), 7.62—7.53(m, 1H), 7.23—7.08(m, 3H), 6.91(dd, J=17.4, 12.0 Hz, 2H), 6.21(s, 1H), 3.93(s, 3H) |
2m | 7.76(d, J=57.1 Hz, 2H), 7.46(s, 2H), 7.39(d, J=10.0 Hz, 3H), 7.25(s, 1H), 7.20(s, 1H), 7.05(d, J=30.0 Hz, 2H), 6.71(d, J=1.4 Hz, 2H), 6.44(s, 1H), 4.87(s, 1H), 3.83(s, 3H) |
2n | 7.66(d, J=15.9 Hz, 1H), 7.50(d, J=15.4 Hz, 2H), 7.19—7.08(m, 2H), 6.98(dd, J=28.2, 11.8 Hz, 2H), 6.86(d, J=15.9 Hz, 1H), 6.73—6.47(m, 2H), 6.04(s, 1H), 3.95(s, 3H) |
3 | 14.89(s, 1H), 8.19—7.92(m, 3H), 7.84(t, J=7.5 Hz, 1H) |
4 | 4.89(s, 1H), 8.18—8.05(m, 2H), 8.03—7.95(m, 1H), 7.84(dd, J=11.9, 4.4 Hz, 1H), 6.40(s, 2H) |
5 | 8.38—8.30(m, 1H), 8.15(t, J=9.9 Hz, 1H), 8.00—7.92(m, 1H), 7.85—7.77(m, 1H), 6.15(s, 2H) |
Table 1 1H NMR data of intermediate compounds 2─5
Compd. | 1H NMR(400 MHz, CDCl3), δ |
---|---|
2a | 7.85(dd, J=15.5, 4.4 Hz, 1H), 7.66(d, J=15.9 Hz, 1H), 7.36(dd, J=31.4, 4.2 Hz, 2H), 7.16(dd, J=8.2, 1.6 Hz, 1H), 7.11—7.05(m, 2H), 6.94(t, J=6.3 Hz, 1H), 6.87(dt, J=13.3, 6.5 Hz, 2H), 6.19(s, 1H), 3.93(s, 3H) |
2b | 7.69(t, J=17.0 Hz, 2H), 7.50(d, J=7.9 Hz, 2H), 7.18(dd, J=20.1, 8.1 Hz, 3H), 7.11—7.00(m, 2H), 6.93(t, J=12.5 Hz, 2H), 3.93(s, 3H), 2.37(s, 3H) |
2c | 8.84(d, J=2.0 Hz, 1H), 8.62(dd, J=4.8, 1.5 Hz, 1H), 7.93(dt, J=8.0, 1.8 Hz, 1H), 7.75—7.67(m, 2H), 7.37(dd, J=7.9, 4.8 Hz, 1H), 7.17(ddd, J=20.9, 7.4, 1.8 Hz, 3H), 6.95(dd, J=9.5, 6.4 Hz, 2H), 6.90(s, 1H), 3.96(s, 3H) |
2d | 8.51(s, 1H), 7.84(d, J=23.6 Hz, 2H), 7.48(s, 1H), 7.40(t, J=5.0 Hz, 3H), 7.20(s, 1H), 7.08(s, 1H), 6.98(s, 1H), 6.37(s, 1H), 4.91(s, 1H), 3.83(s, 3H) |
2f | 8.07(d, J=16.1 Hz, 1H), 7.67(d, J=15.8 Hz, 1H), 7.60(dd, J=7.7, 1.4 Hz, 1H), 7.40—7.32(m, 1H), 7.18—7.08(m, 3H), 7.00—6.89(m, 4H), 6.33(s, 1H), 3.92(s, 3H), 3.89(s, 3H) |
2h | 7.99(d, J=15.7 Hz, 1H), 7.59(dd, J=55.5, 11.6 Hz, 2H), 7.17—7.02(m, 3H), 6.93(d, J=8.9 Hz, 2H), 6.55—6.39(m, 2H), 6.21(s, 1H), 3.92(s, 3H), 3.87(s, 3H), 3.83(s, 3H) |
2i | 7.65(dd, J=16.2, 5.1 Hz, 2H), 7.54(dt, J=10.4, 5.2 Hz, 2H), 7.12(t, J=6.6 Hz, 1H), 7.09—7.02(m, 3H), 7.01—6.96(m, 1H), 6.93(dt, J=8.2, 2.1 Hz, 1H), 6.88(dt, J=15.7, 2.4 Hz, 1H), 6.45(s, 1H), 3.89(s, 3H) |
Compd. | 1H NMR(400 MHz, CDCl3), δ |
2j | 7.82—7.52(m, 3H), 7.40(s, 1H), 7.36(d, J=10.0 Hz, 2H), 7.20(s, 1H), 7.08(s, 1H), 6.93(s, 1H), 6.77(s, 1H), 5.05(s, 1H), 3.87(s, 3H), 3.85(s, 3H), 3.83(s, 3H) |
2k | 7.85—7.65(m, 3H), 7.64—7.55(m, 2H), 7.39(dd, J=9.9, 7.4 Hz, 3H), 7.22—7.05(m, 3H), 7.00—6.87(m, 2H), 3.92(s, 3H) |
2l | 8.44(s, 1H), 8.20(d, J=8.1 Hz, 1H), 7.85(d, J=7.6 Hz, 1H), 7.79—7.65(m, 2H), 7.62—7.53(m, 1H), 7.23—7.08(m, 3H), 6.91(dd, J=17.4, 12.0 Hz, 2H), 6.21(s, 1H), 3.93(s, 3H) |
2m | 7.76(d, J=57.1 Hz, 2H), 7.46(s, 2H), 7.39(d, J=10.0 Hz, 3H), 7.25(s, 1H), 7.20(s, 1H), 7.05(d, J=30.0 Hz, 2H), 6.71(d, J=1.4 Hz, 2H), 6.44(s, 1H), 4.87(s, 1H), 3.83(s, 3H) |
2n | 7.66(d, J=15.9 Hz, 1H), 7.50(d, J=15.4 Hz, 2H), 7.19—7.08(m, 2H), 6.98(dd, J=28.2, 11.8 Hz, 2H), 6.86(d, J=15.9 Hz, 1H), 6.73—6.47(m, 2H), 6.04(s, 1H), 3.95(s, 3H) |
3 | 14.89(s, 1H), 8.19—7.92(m, 3H), 7.84(t, J=7.5 Hz, 1H) |
4 | 4.89(s, 1H), 8.18—8.05(m, 2H), 8.03—7.95(m, 1H), 7.84(dd, J=11.9, 4.4 Hz, 1H), 6.40(s, 2H) |
5 | 8.38—8.30(m, 1H), 8.15(t, J=9.9 Hz, 1H), 8.00—7.92(m, 1H), 7.85—7.77(m, 1H), 6.15(s, 2H) |
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS, m/z(calcd.)[M+H]+ |
---|---|---|---|---|
6a | Yellow solid | 78 | 167—168 | 446.1163(446.1169) |
6b | Yellow solid | 53 | 151—152 | 454.1761(454.1761) |
6c | Yellow solid | 47 | 169—170 | 441.1545(441.1557) |
6d | Yellow solid | 61 | 180—182 | 441.1547(441.1557) |
6e | Yellow solid | 67 | 157—158 | 470.1702(470.1711) |
6f | Yellow solid | 76 | 163—165 | 470.1702(470.1711) |
6g | Yellow solid | 49 | 165—166 | 474.1207(474.1215) |
6h | Yellow solid | 28 | 154—155 | 500.1807(500.1816) |
6i | Yellow solid | 77 | 173—174 | 458.1499(458.1511) |
6j | Yellow solid | 43 | 153—154 | 500.1805(500.1816) |
6k | Yellow solid | 58 | 170—172 | 440.1594(440.1605) |
6l | Yellow solid | 34 | 211—212 | 485.1447(485.1456) |
6m | Yellow solid | 69 | 195—196 | 466.1751(466.1761) |
6n | Yellow solid | 81 | 167—168 | 430.1388(430.1398) |
Table 2 Appearance, yields, melting points and HRMS data for compounds 6a─6n
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS, m/z(calcd.)[M+H]+ |
---|---|---|---|---|
6a | Yellow solid | 78 | 167—168 | 446.1163(446.1169) |
6b | Yellow solid | 53 | 151—152 | 454.1761(454.1761) |
6c | Yellow solid | 47 | 169—170 | 441.1545(441.1557) |
6d | Yellow solid | 61 | 180—182 | 441.1547(441.1557) |
6e | Yellow solid | 67 | 157—158 | 470.1702(470.1711) |
6f | Yellow solid | 76 | 163—165 | 470.1702(470.1711) |
6g | Yellow solid | 49 | 165—166 | 474.1207(474.1215) |
6h | Yellow solid | 28 | 154—155 | 500.1807(500.1816) |
6i | Yellow solid | 77 | 173—174 | 458.1499(458.1511) |
6j | Yellow solid | 43 | 153—154 | 500.1805(500.1816) |
6k | Yellow solid | 58 | 170—172 | 440.1594(440.1605) |
6l | Yellow solid | 34 | 211—212 | 485.1447(485.1456) |
6m | Yellow solid | 69 | 195—196 | 466.1751(466.1761) |
6n | Yellow solid | 81 | 167—168 | 430.1388(430.1398) |
Compd. | 1H NMR(500 or 400 MHz), δ | 13C NMR(125 or 100 MHz), δ |
---|---|---|
6a | 8.27(dd, J=7.9, 1.0 Hz, 1H), 8.21(d, J=7.9 Hz, 1H), 8.12—8.08(m, 1H), 7.96—7.88(m, 2H), 7.73(d, J=5.0 Hz, 1H), 7.66—7.54(m, 2H), 7.43(d, J=1.7 Hz, 1H), 7.31—7.14(m, 4H), 6.93(d, J=15.7 Hz, 1H), 6.26(s, 2H), 3.71(s, 3H) | 188.17, 155.40, 150.85, 147.92, 143.88, 142.84, 140.34, 136.65, 135.90, 134.07, 133.14, 130.92, 130.67, 129.31, 128.96, 125.48, 125.21, 125.08, 123.19, 119.85, 118.20, 112.15, 77.33, 56.22 |
6b | 8.38(dd, J=7.9, 1.0 Hz, 1H), 8.16(dd, J=8.1, 0.5 Hz, 1H), 8.00—7.95(m, 1H), 7.84—7.80(m, 1H), 7.73—7.62(m, 2H), 7.51(d, J=8.1 Hz, 2H), 7.21(d, J=8.0 Hz, 2H), 7.15(dd, J=6.4, 4.7 Hz, 3H), 7.06—6.92(m, 2H), 6.38(s, 2H), 3.84(s, 3H), 2.38(s, 3H) | 188.83, 155.58, 151.08, 147.80, 143.96, 143.28, 142.68, 141.03, 135.44, 132.83, 132.07, 131.00, 129.73, 128.69, 128.43, 125.50, 124.87, 124.39, 122.30, 119.96, 118.70, 111.38, 77.30, 55.91, 21.57 |
Compd. | 1H NMR(500 or 400 MHz), δ | 13C NMR(125 or 100 MHz), δ |
6c | 8.95(s, 1H), 8.63—8.60(m, 1H), 8.31(d, J=7.9 Hz, 1H), 8.24(t, J=7.4 Hz, 2H), 8.17—8.12(m, 1H), 8.01—7.95(m, 1H), 7.78(dd, J=19.7, 10.7 Hz, 2H), 7.54—7.44(m, 3H), 7.35(dd, J=8.3, 1.4 Hz, 1H), 7.29—7.23(m, 2H), 6.31(s, 2H), 3.76(s, 3H) | 188.73, 155.34, 151.36, 150.88, 150.47, 148.02, 143.83, 143.68, 139.44, 136.58, 135.22, 133.99, 131.08, 130.82, 128.90, 127.58, 125.41, 124.45, 123.04, 119.80, 118.31, 112.27, 77.31, 56.19 |
6d | 8.70—8.67(m, 1H), 8.32(dd, J=7.9, 1.0 Hz, 1H), 8.26(d, J=7.6 Hz, 1H), 8.17—8.12(m, 1H), 8.01—7.97(m, 1H), 7.90(td, J=7.7, 1.8 Hz, 1H), 7.81—7.71(m, 3H), 7.63(d, J=15.7 Hz, 1H), 7.51(d, J=1.8 Hz, 1H), 7.44(ddd, J=7.5, 4.7, 1.1 Hz, 1H), 7.40—7.35(m, 2H), 7.26(d, J=8.3 Hz, 1H), 6.31(s, 2H), 3.76(s, 3H) | 189.03, 155.35, 153.33, 150.84, 150.52, 148.00, 143.84, 143.55, 141.91, 137.73, 136.61, 134.02, 130.78, 129.16, 128.92, 125.50, 125.43, 125.28, 125.21, 123.25, 119.81, 118.20, 112.29, 77.29, 56.19 |
6e | 8.28(dd, J=25.2, 7.8 Hz, 2H), 8.15(t, J=7.2 Hz, 1H), 7.99(t, J=7.3 Hz, 1H), 7.77—7.68(m, 4H), 7.45(s, 1H), 7.26(ddd, J=29.4, 21.7, 12.1 Hz, 4H), 7.03(d, J=8.6 Hz, 2H), 6.30(s, 2H), 3.82(s, 3H), 3.76(s, 3H) | 188.69, 161.71, 155.35, 150.89, 147.79, 143.84, 142.89, 142.54, 136.58, 133.99, 131.03, 130.81, 128.90, 127.79, 125.49, 125.42, 123.92, 122.85, 119.81, 118.38, 114.96, 112.22, 77.36, 56.18, 55.85 |
6f | 8.38(dd, J=8.0, 1.0 Hz, 1H), 8.17—8.14(m, 1H), 8.05(d, J=16.1 Hz, 1H), 7.99—7.95(m, 1H), 7.84—7.80(m, 1H), 7.66—7.59(m, 2H), 7.38—7.34(m, 1H), 7.17—7.10(m, 4H), 7.01—6.91(m, 3H), 6.37(s, 2H), 3.91(s, 3H), 3.84(s, 3H) | 188.86, 158.64, 155.32, 150.81, 147.87, 143.80, 142.98, 137.45, 136.54, 133.95, 132.54, 130.88, 128.87, 128.83, 126.10, 125.85, 125.39, 123.44, 122.98, 121.16, 119.77, 118.17, 112.25, 112.14, 77.27, 56.14, 56.13 |
6g | 8.28(dd, J=7.9, 1.3 Hz, 1H), 8.22—8.19(m, 1H), 8.11(td, J=7.9, 1.3 Hz, 1H), 7.97—7.93(m, 1H), 7.79(d, J=8.6 Hz, 2H), 7.72(d, J=2.8 Hz, 1H), 7.68(s, 1H), 7.50—7.48(m, 2H), 7.41(d, J=1.8 Hz, 1H), 7.37(s, 1H), 7.30(dd, J=8.3, 1.8 Hz, 1H), 7.24(d, J=2.0 Hz, 1H), 7.21(d, J=5.7 Hz, 1H), 6.27(s, 2H), 3.72(s, 3H) | 188.87, 155.41, 150.94, 148.02, 143.90, 143.44, 141.49, 136.66, 135.44, 134.29, 134.07, 130.93, 130.72, 129.56, 128.97, 126.70, 125.51, 125.48, 123.05, 119.87, 118.38, 112.32, 77.38, 56.25 |
6h | 8.31(dd, J=7.9, 1.3 Hz, 1H), 8.26—8.23(m, 1H), 8.16—8.12(m, 1H), 8.00—7.96(m, 1H), 7.89(d, J=16.0 Hz, 1H), 7.75(d, J=8.5 Hz, 1H), 7.69(d, J=16.0 Hz, 1H), 7.44(d, J=1.9 Hz, 1H), 7.31(dd, J=8.4, 1.8 Hz, 1H), 7.24(dd, J=12.1, 5.0 Hz, 2H), 7.19(d, J=16.0 Hz, 1H), 6.63(dt, J=8.5, 2.3 Hz, 2H), 6.30(s, 2H), 3.90(s, 3H), 3.84(s, 3H), 3.75(s, 3H) | 193.51, 168.20, 165.15, 160.16, 155.67, 152.55, 148.65, 147.14, 142.55, 141.50, 138.81, 135.84, 135.31, 133.60, 131.08, 130.35, 128.31, 127.68, 124.62, 123.11, 121.18, 116.94, 111.59, 103.66, 82.15, 61.08, 60.97, 60.82 |
6i | 8.37(dd, J=8.0, 1.2 Hz, 1H), 8.15(d, J=8.0 Hz, 1H), 7.96(ddd, J=8.2, 7.3, 1.4 Hz, 1H), 7.84—7.79(m, 1H), 7.65(t, J=16.2 Hz, 2H), 7.60—7.57(m, 2H), 7.15—7.06(m, 5H), 6.95(dd, J=34.9, 15.9 Hz, 2H), 6.37(s, 2H), 3.83(s, 3H) | 186.68, 162.87, 160.40, 153.21, 148.71, 145.77, 141.69, 141.07, 139.54, 134.46, 131.87, 129.75, 129.19, 129.10, 128.74, 126.77, 123.76, 123.29, 120.82, 117.66, 116.13, 114.46, 114.24, 110.07, 75.17, 54.03 |
6j | 8.37—8.34(m, 1H), 8.15—8.13(m, 1H), 7.96(ddd, J=8.1, 6.1, 1.4 Hz, 1H), 7.82—7.79(m, 1H), 7.64(t, J=16.0 Hz, 2H), 7.17(dd, J=8.4, 1.9 Hz, 1H), 7.14—7.10(m, 4H), 6.96—6.85(m, 3H), 6.35(s, 2H), 3.92(s, 3H), 3.90(s, 3H), 3.82(s, 3H) | 188.72, 155.66, 151.43, 151.09, 149.28, 147.81, 144.01, 143.41, 142.60, 135.53, 132.92, 131.08, 128.76, 127.81, 125.56, 124.77, 123.63, 123.30, 122.34, 120.00, 118.69, 111.43, 111.14, 109.86, 77.36, 56.09, 56.01, 55.97 |
6k | 8.36(dd, J=7.7, 2.8 Hz, 1H), 8.14(dd, J=8.0, 3.4 Hz, 1H), 7.99—7.91(m, 1H), 7.80(td, J=7.3, 3.2 Hz, 1H), 7.74—7.56(m, 4H), 7.44—7.36(m, 3H), 7.17—7.03(m, 4H), 6.93(dt, J=13.7, 6.9 Hz, 1H), 6.36(s, 2H), 3.82(s, 3H) | 188.86, 155.67, 151.12, 147.94, 144.01, 143.28, 143.02, 135.53, 134.88, 132.93, 130.96, 130.57, 129.05, 128.76, 128.48, 125.56, 125.34, 124.86, 122.44, 120.01, 118.69, 111.45, 77.35, 55.98 |
Compd. | 1H NMR(500 or 400 MHz), δ | 13C NMR(125 or 100 MHz), δ |
6l | 8.58(d, J=1.3 Hz, 1H), 8.24(ddd, J=29.7, 9.4, 4.5 Hz, 5H), 8.12—8.08(m, 1H), 7.96—7.92(m, 1H), 7.79(ddd, J=24.7, 16.1, 2.2 Hz, 2H), 7.71(td, J=8.1, 2.6 Hz, 1H), 7.52(dd, J=16.1, 2.6 Hz, 1H), 7.41(s, 1H), 7.31(d, J=8.3 Hz, 1H), 7.23(dd, J=8.4, 2.6 Hz, 1H), 6.26(s, 2H), 3.71(s, 3H) | 188.86, 155.41, 150.95, 148.91, 148.12, 143.90, 143.87, 140.43, 137.22, 136.67, 135.04, 134.08, 131.00, 130.86, 128.98, 128.49, 125.48, 125.47, 125.09, 123.31, 123.14, 119.87, 118.36, 112.33, 77.38, 56.26 |
6m | 8.28(d, J=7.9 Hz, 1H), 8.22(d, J=8.0 Hz, 1H), 8.12(t, J=7.7 Hz, 1H), 7.95(t, J=7.6 Hz, 1H), 7.60—7.52(m, 4H), 7.39(dd, J=18.6, 10.7 Hz, 3H), 7.34—7.27(m, 3H), 7.18(dd, J=25.5, 8.6 Hz, 3H), 6.70(d, J=15.2 Hz, 1H), 6.26(s, 2H), 3.72(s, 3H) | 188.81, 155.41, 150.96, 147.92, 143.91, 143.71, 142.63, 141.66, 136.66, 136.56, 134.07, 131.01, 130.23, 129.71, 129.46, 128.97, 127.98, 127.82, 125.49, 124.89, 123.11, 119.88, 118.43, 112.30, 77.42, 56.28 |
6n | 8.33—8.29(m, 1H), 8.25(dt, J=6.4, 3.2 Hz, 1H), 8.17—8.11(m, 2H), 8.01—7.95(m, 2H), 7.91(d, J=1.5 Hz, 1H), 7.69—7.56(m, 2H), 7.48(d, J=1.8 Hz, 1H), 7.33(d, J=2.7 Hz, 1H), 7.00(dd, J=11.8, 9.6 Hz, 2H), 6.69(dd, J=3.4, 1.8 Hz, 1H), 6.30(s, 2H), 3.75(s, 3H) | 188.20, 155.35, 151.47, 150.84, 147.87, 146.58, 143.83, 142.78, 136.59, 134.01, 130.90, 129.59, 128.90, 125.42, 125.24, 123.32, 123.10, 119.80, 118.26, 117.10, 113.57, 112.20, 77.31, 56.17 |
Table 3 1H NMR and 13C NMR data of compounds 6a—6n*
Compd. | 1H NMR(500 or 400 MHz), δ | 13C NMR(125 or 100 MHz), δ |
---|---|---|
6a | 8.27(dd, J=7.9, 1.0 Hz, 1H), 8.21(d, J=7.9 Hz, 1H), 8.12—8.08(m, 1H), 7.96—7.88(m, 2H), 7.73(d, J=5.0 Hz, 1H), 7.66—7.54(m, 2H), 7.43(d, J=1.7 Hz, 1H), 7.31—7.14(m, 4H), 6.93(d, J=15.7 Hz, 1H), 6.26(s, 2H), 3.71(s, 3H) | 188.17, 155.40, 150.85, 147.92, 143.88, 142.84, 140.34, 136.65, 135.90, 134.07, 133.14, 130.92, 130.67, 129.31, 128.96, 125.48, 125.21, 125.08, 123.19, 119.85, 118.20, 112.15, 77.33, 56.22 |
6b | 8.38(dd, J=7.9, 1.0 Hz, 1H), 8.16(dd, J=8.1, 0.5 Hz, 1H), 8.00—7.95(m, 1H), 7.84—7.80(m, 1H), 7.73—7.62(m, 2H), 7.51(d, J=8.1 Hz, 2H), 7.21(d, J=8.0 Hz, 2H), 7.15(dd, J=6.4, 4.7 Hz, 3H), 7.06—6.92(m, 2H), 6.38(s, 2H), 3.84(s, 3H), 2.38(s, 3H) | 188.83, 155.58, 151.08, 147.80, 143.96, 143.28, 142.68, 141.03, 135.44, 132.83, 132.07, 131.00, 129.73, 128.69, 128.43, 125.50, 124.87, 124.39, 122.30, 119.96, 118.70, 111.38, 77.30, 55.91, 21.57 |
Compd. | 1H NMR(500 or 400 MHz), δ | 13C NMR(125 or 100 MHz), δ |
6c | 8.95(s, 1H), 8.63—8.60(m, 1H), 8.31(d, J=7.9 Hz, 1H), 8.24(t, J=7.4 Hz, 2H), 8.17—8.12(m, 1H), 8.01—7.95(m, 1H), 7.78(dd, J=19.7, 10.7 Hz, 2H), 7.54—7.44(m, 3H), 7.35(dd, J=8.3, 1.4 Hz, 1H), 7.29—7.23(m, 2H), 6.31(s, 2H), 3.76(s, 3H) | 188.73, 155.34, 151.36, 150.88, 150.47, 148.02, 143.83, 143.68, 139.44, 136.58, 135.22, 133.99, 131.08, 130.82, 128.90, 127.58, 125.41, 124.45, 123.04, 119.80, 118.31, 112.27, 77.31, 56.19 |
6d | 8.70—8.67(m, 1H), 8.32(dd, J=7.9, 1.0 Hz, 1H), 8.26(d, J=7.6 Hz, 1H), 8.17—8.12(m, 1H), 8.01—7.97(m, 1H), 7.90(td, J=7.7, 1.8 Hz, 1H), 7.81—7.71(m, 3H), 7.63(d, J=15.7 Hz, 1H), 7.51(d, J=1.8 Hz, 1H), 7.44(ddd, J=7.5, 4.7, 1.1 Hz, 1H), 7.40—7.35(m, 2H), 7.26(d, J=8.3 Hz, 1H), 6.31(s, 2H), 3.76(s, 3H) | 189.03, 155.35, 153.33, 150.84, 150.52, 148.00, 143.84, 143.55, 141.91, 137.73, 136.61, 134.02, 130.78, 129.16, 128.92, 125.50, 125.43, 125.28, 125.21, 123.25, 119.81, 118.20, 112.29, 77.29, 56.19 |
6e | 8.28(dd, J=25.2, 7.8 Hz, 2H), 8.15(t, J=7.2 Hz, 1H), 7.99(t, J=7.3 Hz, 1H), 7.77—7.68(m, 4H), 7.45(s, 1H), 7.26(ddd, J=29.4, 21.7, 12.1 Hz, 4H), 7.03(d, J=8.6 Hz, 2H), 6.30(s, 2H), 3.82(s, 3H), 3.76(s, 3H) | 188.69, 161.71, 155.35, 150.89, 147.79, 143.84, 142.89, 142.54, 136.58, 133.99, 131.03, 130.81, 128.90, 127.79, 125.49, 125.42, 123.92, 122.85, 119.81, 118.38, 114.96, 112.22, 77.36, 56.18, 55.85 |
6f | 8.38(dd, J=8.0, 1.0 Hz, 1H), 8.17—8.14(m, 1H), 8.05(d, J=16.1 Hz, 1H), 7.99—7.95(m, 1H), 7.84—7.80(m, 1H), 7.66—7.59(m, 2H), 7.38—7.34(m, 1H), 7.17—7.10(m, 4H), 7.01—6.91(m, 3H), 6.37(s, 2H), 3.91(s, 3H), 3.84(s, 3H) | 188.86, 158.64, 155.32, 150.81, 147.87, 143.80, 142.98, 137.45, 136.54, 133.95, 132.54, 130.88, 128.87, 128.83, 126.10, 125.85, 125.39, 123.44, 122.98, 121.16, 119.77, 118.17, 112.25, 112.14, 77.27, 56.14, 56.13 |
6g | 8.28(dd, J=7.9, 1.3 Hz, 1H), 8.22—8.19(m, 1H), 8.11(td, J=7.9, 1.3 Hz, 1H), 7.97—7.93(m, 1H), 7.79(d, J=8.6 Hz, 2H), 7.72(d, J=2.8 Hz, 1H), 7.68(s, 1H), 7.50—7.48(m, 2H), 7.41(d, J=1.8 Hz, 1H), 7.37(s, 1H), 7.30(dd, J=8.3, 1.8 Hz, 1H), 7.24(d, J=2.0 Hz, 1H), 7.21(d, J=5.7 Hz, 1H), 6.27(s, 2H), 3.72(s, 3H) | 188.87, 155.41, 150.94, 148.02, 143.90, 143.44, 141.49, 136.66, 135.44, 134.29, 134.07, 130.93, 130.72, 129.56, 128.97, 126.70, 125.51, 125.48, 123.05, 119.87, 118.38, 112.32, 77.38, 56.25 |
6h | 8.31(dd, J=7.9, 1.3 Hz, 1H), 8.26—8.23(m, 1H), 8.16—8.12(m, 1H), 8.00—7.96(m, 1H), 7.89(d, J=16.0 Hz, 1H), 7.75(d, J=8.5 Hz, 1H), 7.69(d, J=16.0 Hz, 1H), 7.44(d, J=1.9 Hz, 1H), 7.31(dd, J=8.4, 1.8 Hz, 1H), 7.24(dd, J=12.1, 5.0 Hz, 2H), 7.19(d, J=16.0 Hz, 1H), 6.63(dt, J=8.5, 2.3 Hz, 2H), 6.30(s, 2H), 3.90(s, 3H), 3.84(s, 3H), 3.75(s, 3H) | 193.51, 168.20, 165.15, 160.16, 155.67, 152.55, 148.65, 147.14, 142.55, 141.50, 138.81, 135.84, 135.31, 133.60, 131.08, 130.35, 128.31, 127.68, 124.62, 123.11, 121.18, 116.94, 111.59, 103.66, 82.15, 61.08, 60.97, 60.82 |
6i | 8.37(dd, J=8.0, 1.2 Hz, 1H), 8.15(d, J=8.0 Hz, 1H), 7.96(ddd, J=8.2, 7.3, 1.4 Hz, 1H), 7.84—7.79(m, 1H), 7.65(t, J=16.2 Hz, 2H), 7.60—7.57(m, 2H), 7.15—7.06(m, 5H), 6.95(dd, J=34.9, 15.9 Hz, 2H), 6.37(s, 2H), 3.83(s, 3H) | 186.68, 162.87, 160.40, 153.21, 148.71, 145.77, 141.69, 141.07, 139.54, 134.46, 131.87, 129.75, 129.19, 129.10, 128.74, 126.77, 123.76, 123.29, 120.82, 117.66, 116.13, 114.46, 114.24, 110.07, 75.17, 54.03 |
6j | 8.37—8.34(m, 1H), 8.15—8.13(m, 1H), 7.96(ddd, J=8.1, 6.1, 1.4 Hz, 1H), 7.82—7.79(m, 1H), 7.64(t, J=16.0 Hz, 2H), 7.17(dd, J=8.4, 1.9 Hz, 1H), 7.14—7.10(m, 4H), 6.96—6.85(m, 3H), 6.35(s, 2H), 3.92(s, 3H), 3.90(s, 3H), 3.82(s, 3H) | 188.72, 155.66, 151.43, 151.09, 149.28, 147.81, 144.01, 143.41, 142.60, 135.53, 132.92, 131.08, 128.76, 127.81, 125.56, 124.77, 123.63, 123.30, 122.34, 120.00, 118.69, 111.43, 111.14, 109.86, 77.36, 56.09, 56.01, 55.97 |
6k | 8.36(dd, J=7.7, 2.8 Hz, 1H), 8.14(dd, J=8.0, 3.4 Hz, 1H), 7.99—7.91(m, 1H), 7.80(td, J=7.3, 3.2 Hz, 1H), 7.74—7.56(m, 4H), 7.44—7.36(m, 3H), 7.17—7.03(m, 4H), 6.93(dt, J=13.7, 6.9 Hz, 1H), 6.36(s, 2H), 3.82(s, 3H) | 188.86, 155.67, 151.12, 147.94, 144.01, 143.28, 143.02, 135.53, 134.88, 132.93, 130.96, 130.57, 129.05, 128.76, 128.48, 125.56, 125.34, 124.86, 122.44, 120.01, 118.69, 111.45, 77.35, 55.98 |
Compd. | 1H NMR(500 or 400 MHz), δ | 13C NMR(125 or 100 MHz), δ |
6l | 8.58(d, J=1.3 Hz, 1H), 8.24(ddd, J=29.7, 9.4, 4.5 Hz, 5H), 8.12—8.08(m, 1H), 7.96—7.92(m, 1H), 7.79(ddd, J=24.7, 16.1, 2.2 Hz, 2H), 7.71(td, J=8.1, 2.6 Hz, 1H), 7.52(dd, J=16.1, 2.6 Hz, 1H), 7.41(s, 1H), 7.31(d, J=8.3 Hz, 1H), 7.23(dd, J=8.4, 2.6 Hz, 1H), 6.26(s, 2H), 3.71(s, 3H) | 188.86, 155.41, 150.95, 148.91, 148.12, 143.90, 143.87, 140.43, 137.22, 136.67, 135.04, 134.08, 131.00, 130.86, 128.98, 128.49, 125.48, 125.47, 125.09, 123.31, 123.14, 119.87, 118.36, 112.33, 77.38, 56.26 |
6m | 8.28(d, J=7.9 Hz, 1H), 8.22(d, J=8.0 Hz, 1H), 8.12(t, J=7.7 Hz, 1H), 7.95(t, J=7.6 Hz, 1H), 7.60—7.52(m, 4H), 7.39(dd, J=18.6, 10.7 Hz, 3H), 7.34—7.27(m, 3H), 7.18(dd, J=25.5, 8.6 Hz, 3H), 6.70(d, J=15.2 Hz, 1H), 6.26(s, 2H), 3.72(s, 3H) | 188.81, 155.41, 150.96, 147.92, 143.91, 143.71, 142.63, 141.66, 136.66, 136.56, 134.07, 131.01, 130.23, 129.71, 129.46, 128.97, 127.98, 127.82, 125.49, 124.89, 123.11, 119.88, 118.43, 112.30, 77.42, 56.28 |
6n | 8.33—8.29(m, 1H), 8.25(dt, J=6.4, 3.2 Hz, 1H), 8.17—8.11(m, 2H), 8.01—7.95(m, 2H), 7.91(d, J=1.5 Hz, 1H), 7.69—7.56(m, 2H), 7.48(d, J=1.8 Hz, 1H), 7.33(d, J=2.7 Hz, 1H), 7.00(dd, J=11.8, 9.6 Hz, 2H), 6.69(dd, J=3.4, 1.8 Hz, 1H), 6.30(s, 2H), 3.75(s, 3H) | 188.20, 155.35, 151.47, 150.84, 147.87, 146.58, 143.83, 142.78, 136.59, 134.01, 130.90, 129.59, 128.90, 125.42, 125.24, 123.32, 123.10, 119.80, 118.26, 117.10, 113.57, 112.20, 77.31, 56.17 |
Compd. | Xac | R. solanacearum | ||
---|---|---|---|---|
100 μg/mL | 50 μg/mL | 100 μg/mL | 50 μg/mL | |
6a | 55.4±4.2 | 49.6±3.1 | 51.8±2.6 | 39.9±0.9 |
6b | 68.8±5.2 | 62.8±6.3 | 34.5±1.0 | 31.1±6.0 |
6c | 48.5±3.9 | 38.9±4.9 | 47.7±1.6 | 33.5±4.2 |
6d | 47.5±5.0 | 43.5±4.4 | 53.0±7.5 | 37.0±1.3 |
6e | 50.4±3.5 | 41.3±6.1 | 42.1±2.9 | 38.2±5.4 |
6f | 48.9±5.0 | 37.6±2.0 | 44.6±4.7 | 31.6±7.4 |
6g | 64.1±1.4 | 53.1±9.1 | 35.5±3.3 | 30.1±3.1 |
6h | 49.4±4.0 | 46.7±1.0 | 50.7±6.1 | 44.2±2.9 |
6i | 63.7±6.6 | 55.9±1.4 | 76.9±3.2 | 48.4±1.7 |
6j | 71.0±2.9 | 43.7±9.6 | 48.8±3.4 | 32.4±1.4 |
6k | 64.8±7.1 | 57.5±1.2 | 39.5±3.6 | 25.9±8.5 |
6l | 100.0±7.5 | 70.3±3.5 | 48.7±3.3 | 25.6±0.6 |
6m | 33.3±8.6 | 31.2±1.2 | 43.0±8.2 | 39.8±1.2 |
6n | 51.1±3.4 | 43.8±2.0 | 31.1±1.4 | 26.3±7.5 |
Thiodiazole copper | 67.7±3.7 | 44.3±4.1 | 37.0±3.8 | 21.0±4.4 |
Table 4 Antibacterial activity(%) of the title compounds*
Compd. | Xac | R. solanacearum | ||
---|---|---|---|---|
100 μg/mL | 50 μg/mL | 100 μg/mL | 50 μg/mL | |
6a | 55.4±4.2 | 49.6±3.1 | 51.8±2.6 | 39.9±0.9 |
6b | 68.8±5.2 | 62.8±6.3 | 34.5±1.0 | 31.1±6.0 |
6c | 48.5±3.9 | 38.9±4.9 | 47.7±1.6 | 33.5±4.2 |
6d | 47.5±5.0 | 43.5±4.4 | 53.0±7.5 | 37.0±1.3 |
6e | 50.4±3.5 | 41.3±6.1 | 42.1±2.9 | 38.2±5.4 |
6f | 48.9±5.0 | 37.6±2.0 | 44.6±4.7 | 31.6±7.4 |
6g | 64.1±1.4 | 53.1±9.1 | 35.5±3.3 | 30.1±3.1 |
6h | 49.4±4.0 | 46.7±1.0 | 50.7±6.1 | 44.2±2.9 |
6i | 63.7±6.6 | 55.9±1.4 | 76.9±3.2 | 48.4±1.7 |
6j | 71.0±2.9 | 43.7±9.6 | 48.8±3.4 | 32.4±1.4 |
6k | 64.8±7.1 | 57.5±1.2 | 39.5±3.6 | 25.9±8.5 |
6l | 100.0±7.5 | 70.3±3.5 | 48.7±3.3 | 25.6±0.6 |
6m | 33.3±8.6 | 31.2±1.2 | 43.0±8.2 | 39.8±1.2 |
6n | 51.1±3.4 | 43.8±2.0 | 31.1±1.4 | 26.3±7.5 |
Thiodiazole copper | 67.7±3.7 | 44.3±4.1 | 37.0±3.8 | 21.0±4.4 |
Compd. | Xac | R. solanacearum | ||||
---|---|---|---|---|---|---|
Toxic regression equation | R | EC50/(μg·mL-1) | Toxic regression equation | R | EC50/(μg·mL-1) | |
6a | y=0.7585x+3.6658 | 0.9636 | 36.91 | y=1.6440x+1.9350 | 0.9572 | 58.88 |
6b | y=1.8883x+2.0443 | 0.8825 | 32.63 | — | — | — |
6d | — | — | — | y=1.2655x+2.5155 | 0.9914 | 65.95 |
6h | — | — | — | y=1.4337x+2.3087 | 0.9699 | 56.69 |
6i | y=1.1422x+3.1308 | 0.9746 | 36.63 | y=1.7907x+1.8750 | 0.9196 | 48.77 |
6j | y=1.7273x+2.0235 | 0.9930 | 47.47 | y=0.9359x+3.0598 | 0.9737 | 57.18 |
6k | y=0.9454x+3.4569 | 0.9384 | 33.96 | — | — | — |
6l | y=1.8390x+2.3078 | 0.9809 | 27.44 | — | — | — |
Thiodiazole copper | y=2.3250x+1.4553 | 0.9930 | 51.35 | y=1.0416x+2.5385 | 0.9766 | 87.26 |
Table 5 EC50 values of the title compounds against Xac and R. solanacearum
Compd. | Xac | R. solanacearum | ||||
---|---|---|---|---|---|---|
Toxic regression equation | R | EC50/(μg·mL-1) | Toxic regression equation | R | EC50/(μg·mL-1) | |
6a | y=0.7585x+3.6658 | 0.9636 | 36.91 | y=1.6440x+1.9350 | 0.9572 | 58.88 |
6b | y=1.8883x+2.0443 | 0.8825 | 32.63 | — | — | — |
6d | — | — | — | y=1.2655x+2.5155 | 0.9914 | 65.95 |
6h | — | — | — | y=1.4337x+2.3087 | 0.9699 | 56.69 |
6i | y=1.1422x+3.1308 | 0.9746 | 36.63 | y=1.7907x+1.8750 | 0.9196 | 48.77 |
6j | y=1.7273x+2.0235 | 0.9930 | 47.47 | y=0.9359x+3.0598 | 0.9737 | 57.18 |
6k | y=0.9454x+3.4569 | 0.9384 | 33.96 | — | — | — |
6l | y=1.8390x+2.3078 | 0.9809 | 27.44 | — | — | — |
Thiodiazole copper | y=2.3250x+1.4553 | 0.9930 | 51.35 | y=1.0416x+2.5385 | 0.9766 | 87.26 |
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