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Design and synthesis of new 7, 8-dimethoxy-α-naphthoflavones as CYP1A1 inhibitors

Jia-Hua Cui ,  Dagula Hu ,  Xu Zhang ,  Zheng Jing ,  Jing Ding ,  Ru-Bing Wang ,  Shao-Shun Li

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Citation:  Jia-Hua Cui, Dagula Hu, Xu Zhang, Zheng Jing, Jing Ding, Ru-Bing Wang, Shao-Shun Li. Design and synthesis of new 7, 8-dimethoxy-α-naphthoflavones as CYP1A1 inhibitors[J]. Chinese Chemical Letters, 2013, 24(3): 215-218. shu

Design and synthesis of new 7, 8-dimethoxy-α-naphthoflavones as CYP1A1 inhibitors

    • 通讯作者: Shao-Shun Li,
摘要: The flavonoids as inhibitors of CYP1A1 exhibit chemopreventive effects against certain procarcinogens and have been considered as the promising cancer preventive agents. A series of novel 7,8-dimethoxy-α-naphthoflavones as the substrate analogs were designed and prepared. The enzyme assay suggested that all of these new flavones were stronger inhibitors of CYP1A1 than the lead compound a-naphthoflavone. Among the tested ones, 3h showed the most potent inhibitory effects.

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    20. [20] The spectroscopic data of compound 9 and 10. 9: White crystals; mp 89-91℃; IR (KBr, cm-1): v 2965, 2933, 1761vs (C=O), 1369, 1274, 1212, 1079, 1007; 1H NMR (300 MHz, CDCl3): δ 8.02 (d, 1H, J = 9.0 Hz, H-C(4)), 7.61 (d, 1H, J = 9.0 Hz, H-C(8)), 7.45 (dd, 1H, J = 7.2, 9.0 Hz, H-C(3)), 7.31 (d, 1H, J = 9.0 Hz, H-C(7)), 7.11 (d, 1H, J = 7.2 Hz, H-C(2)), 3.99 (s, 6H, CH3O), 2.45 (s, 3H, CH3CO); 13C NMR (100 MHz, CDCl3): δ 169.4 (quat., C=O), 148.8, 146.7, 143.1, 130.6, 122.9 (quat., 5 CAr,), 125.7, 119.5, 117.5, 116.2, 115.6 (5 CArH), 61.1 (OCH3), 56.8 (OCH3), 20.9 (CH3); ESIHRMS: Calcd. for C14H15O4 247.0970; found 247.0958 [M+H]+. 10: Light yellow plates; mp 136-138℃; IR (KBr, cm-1): v 2980, 2950, 1622vs (C=O), 1497, 1488, 1394, 1281, 1085; 1H NMR (CDCl3, 300 MHz): δ 14.15 (s, 1H, OH), 8.23 (d, 1H, J = 9.3 Hz, H-C(4)), 7.61 (d, 1H, J = 9.0 Hz, H-C(8)), 7.51 (d, 1H, J = 9.0 Hz, H-C(7)), 7.28 (d, 1H, J = 9.3 Hz, H-C(3)), 4.02 (s, 3H, CH3O), 3.96 (s, 3H, CH3O), 2.67 (s, 3H, CH3CO). 13C NMR (100 MHz, CDCl3): δ 203.8 (quat., C=O), 162.9, 152.3, 142.4,133.0, 120.4, 111.8 (quat., 6 CAr), 125.2, 121.4, 113.4, 111.6 (4 CArH), 61.1 (OCH3), 56.3 (OCH3), 26.6 (CH3); ESI-HRMS: Calcd. for C14H15O4 247.0970; found 247.0964 [M+H]+.[20] The spectroscopic data of compound 9 and 10. 9: White crystals; mp 89-91℃; IR (KBr, cm-1): v 2965, 2933, 1761vs (C=O), 1369, 1274, 1212, 1079, 1007; 1H NMR (300 MHz, CDCl3): δ 8.02 (d, 1H, J = 9.0 Hz, H-C(4)), 7.61 (d, 1H, J = 9.0 Hz, H-C(8)), 7.45 (dd, 1H, J = 7.2, 9.0 Hz, H-C(3)), 7.31 (d, 1H, J = 9.0 Hz, H-C(7)), 7.11 (d, 1H, J = 7.2 Hz, H-C(2)), 3.99 (s, 6H, CH3O), 2.45 (s, 3H, CH3CO); 13C NMR (100 MHz, CDCl3): δ 169.4 (quat., C=O), 148.8, 146.7, 143.1, 130.6, 122.9 (quat., 5 CAr,), 125.7, 119.5, 117.5, 116.2, 115.6 (5 CArH), 61.1 (OCH3), 56.8 (OCH3), 20.9 (CH3); ESIHRMS: Calcd. for C14H15O4 247.0970; found 247.0958 [M+H]+. 10: Light yellow plates; mp 136-138℃; IR (KBr, cm-1): v 2980, 2950, 1622vs (C=O), 1497, 1488, 1394, 1281, 1085; 1H NMR (CDCl3, 300 MHz): δ 14.15 (s, 1H, OH), 8.23 (d, 1H, J = 9.3 Hz, H-C(4)), 7.61 (d, 1H, J = 9.0 Hz, H-C(8)), 7.51 (d, 1H, J = 9.0 Hz, H-C(7)), 7.28 (d, 1H, J = 9.3 Hz, H-C(3)), 4.02 (s, 3H, CH3O), 3.96 (s, 3H, CH3O), 2.67 (s, 3H, CH3CO). 13C NMR (100 MHz, CDCl3): δ 203.8 (quat., C=O), 162.9, 152.3, 142.4,133.0, 120.4, 111.8 (quat., 6 CAr), 125.2, 121.4, 113.4, 111.6 (4 CArH), 61.1 (OCH3), 56.3 (OCH3), 26.6 (CH3); ESI-HRMS: Calcd. for C14H15O4 247.0970; found 247.0964 [M+H]+.

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    22. [22] The spectroscopic data of compounds 3a-3j. 3a: Pale yellow crystals; mp 175-176℃; 1H NMR (300 MHz, CDCl3): δ 8.38 (d, 1H, J = 9.0 Hz), 8.15 (d, 1H, J = 9.0 Hz), 8.07 (d, 1H, J = 9.0 Hz), 8.02 (m, 2H, H-C(2'), H-C(6')), 7.58 (m, 3H, H-C(3'), H-C(4'), H-C(5')), 7.46 (d, 1H, J = 9.0 Hz), 6.96 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H17O4 333.1127; found 333.1119 [M+H]+. 3b: Pale-yellow needles; mp 207-209℃; 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J = 9.0 Hz), 8.13 (d, 1H, J = 9.0 Hz), 8.04 (d, 1H, J = 9.0 Hz), 7.95 (d, 2H, J = 9.0 Hz, H-C(2'), H-C(6')), 7.44 (d, 1H, J = 9.0 Hz), 7.07 (d, 2H, J = 9.0 Hz, H-C(30), H-C(50)), 6.85 (s, 1H, H-C(3)), 4.06 (s, 3H, CH3O), 4.03 (s, 3H, CH3O), 3.91 (s, 3H, CH3O); ESI-HRMS: Calcd. for C22H19O5 363.1233; found 363.1217 [M+H]+. 3c: While needles; mp 190-191℃; 1H NMR (300 MHz, CDCl3): δ 8.31 (d, 1H, J = 9.0 Hz), 8.14 (d, 1H, J = 9.0 Hz), 8.02 (m, 2H), 7.51 (m, 1H), 7.42 (d, 1H, J = 9.0 Hz), 7.25 (s, 1H), 7.17 (m, 1H), 7.08 (d, 1H, J = 8.4 Hz, H-C(3')), 4.05 (s, 3H, CH3O), 4.02 (s, 3H, CH3O), 3.96 (s, 3H, CH3O); ESI-HRMS: Calcd. for C22H19O5 363.1233; found 363.1221 [M+H]+. 3d: Pale yellow crystals; mp 220-222℃; 1H NMR (300 MHz, CDCl3): δ 8.31 (d, 1H, J = 9.0 Hz), 8.13 (d, 1H, J = 9.0 Hz), 8.05 (d, 1H, J = 9.0 Hz), 7.65 (d, 1H, J = 8.4 Hz, H-C(6')), 7.45 (m, 2H, H-C(2'), H-C(5')), 7.04 (d, 1H, J = 9.0 Hz), 6.86 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O), 4.02 (s, 3H, CH3O), 3.99 (s, 3H, CH3O); ESI-HRMS: Calcd. for C23H21O6 393.1338; found 393.1345 [M+H]+. 3e: Pale yellow needles; mp 204-206℃; 1H NMR (300 MHz, CDCl3): δ 8.32 (d, 1H, J = 9.3 Hz), 8.13 (d, 1H, J = 9.0 Hz), 8.07 (d, 1H, J = 9.0 Hz), 7.94 (d, 2H, J = 8.4 Hz), 7.55 (d, 2H, J = 8.4 Hz), 7.46 (d, 1H, J = 9.3 Hz), 6.91 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H16O4 367.0737; found 367.0728 [M+H]+. 3f: Light yellow needles; mp 193-195℃; 1H NMR (300 MHz, CDCl3): δ 8.31 (d, 1H, J = 9.0 Hz), 8.16 (d, 1H, J = 9.0 Hz), 8.08 (d, 1H, J = 9.0 Hz), 7.70 (m, 1H, H-C(6')), 7.59 (d, 1H, J = 7.2 Hz, H-C(3')), 7.48 (m, 2H, H-C(40), H-C(5')), 7.41 (d, 1H, J = 9.0 Hz), 6.79 (s, 1H, H-C(3)), 4.05 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H16O4 367.0737; found 367.0733 [M+H]+. 3g: Light yellow needles; mp 194-195℃; 1H NMR (300 MHz, CDCl3): δ 8.32 (d, 1H, J = 9.0 Hz), 8.12 (d, 1H, J = 9.0 Hz), 8.06 (d, 1H, J = 9.0 Hz), 7.98 (s, 1H, H-C(2')), 7.85 (d, 1H, J = 6.6 Hz), 7.53 (m, 2H), 7.47 (d, 1H, J = 9.0 Hz), 6.91 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H16O4 367.0737; found 367.0726 [M+H]+. 3 h: Pale yellow needles; mp 206-208℃; 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J = 9.0 Hz), 8.13 (d, 1H, J = 9.0 Hz), 8.07 (d, 1H, J = 9.0 Hz), 8.01 (m, 2H), 7.46 (d, 1H, J = 9.0 Hz), 7.27 (m, 2H), 6.88 (s, 1H, HC(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H16FO4 351.1033; found 351.1024 [M+H]+. 3i: Pale yellow crystals; mp 192-193℃; 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J = 9.0 Hz), 8.14 (d, 1H, J = 9.0 Hz), 8.07 (d, 1H, J = 9.0 Hz), 8.00 (m, 1H, H-C(6')), 7.55 (m, 1H), 7.45 (d, 1H, J = 9.0 Hz), 7.38 (m, 1H), 7.28 (m, 1H), 7.04 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESIHRMS: Calcd. for C21H16FO4 351.1033; found 351.1045 [M+H]+. 3j: Light yellow crystals; mp 192-194℃; 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J = 9.0 Hz), 8.12 (d, 1H, J = 9.0 Hz), 8.06 (d, 1H, J = 9.0 Hz), 7.76 (d, 1H, J = 7.5 Hz, H-C(60)), 7.73 (m, 1H), 7.55 (m, 1H), 7.47 (d, 1H, J = 9.0 Hz), 7.27 (m, 1H), 6.93 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H16FO4 351.1033; found 351.1020 [M+H]+.[22] The spectroscopic data of compounds 3a-3j. 3a: Pale yellow crystals; mp 175-176℃; 1H NMR (300 MHz, CDCl3): δ 8.38 (d, 1H, J = 9.0 Hz), 8.15 (d, 1H, J = 9.0 Hz), 8.07 (d, 1H, J = 9.0 Hz), 8.02 (m, 2H, H-C(2'), H-C(6')), 7.58 (m, 3H, H-C(3'), H-C(4'), H-C(5')), 7.46 (d, 1H, J = 9.0 Hz), 6.96 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H17O4 333.1127; found 333.1119 [M+H]+. 3b: Pale-yellow needles; mp 207-209℃; 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J = 9.0 Hz), 8.13 (d, 1H, J = 9.0 Hz), 8.04 (d, 1H, J = 9.0 Hz), 7.95 (d, 2H, J = 9.0 Hz, H-C(2'), H-C(6')), 7.44 (d, 1H, J = 9.0 Hz), 7.07 (d, 2H, J = 9.0 Hz, H-C(30), H-C(50)), 6.85 (s, 1H, H-C(3)), 4.06 (s, 3H, CH3O), 4.03 (s, 3H, CH3O), 3.91 (s, 3H, CH3O); ESI-HRMS: Calcd. for C22H19O5 363.1233; found 363.1217 [M+H]+. 3c: While needles; mp 190-191℃; 1H NMR (300 MHz, CDCl3): δ 8.31 (d, 1H, J = 9.0 Hz), 8.14 (d, 1H, J = 9.0 Hz), 8.02 (m, 2H), 7.51 (m, 1H), 7.42 (d, 1H, J = 9.0 Hz), 7.25 (s, 1H), 7.17 (m, 1H), 7.08 (d, 1H, J = 8.4 Hz, H-C(3')), 4.05 (s, 3H, CH3O), 4.02 (s, 3H, CH3O), 3.96 (s, 3H, CH3O); ESI-HRMS: Calcd. for C22H19O5 363.1233; found 363.1221 [M+H]+. 3d: Pale yellow crystals; mp 220-222℃; 1H NMR (300 MHz, CDCl3): δ 8.31 (d, 1H, J = 9.0 Hz), 8.13 (d, 1H, J = 9.0 Hz), 8.05 (d, 1H, J = 9.0 Hz), 7.65 (d, 1H, J = 8.4 Hz, H-C(6')), 7.45 (m, 2H, H-C(2'), H-C(5')), 7.04 (d, 1H, J = 9.0 Hz), 6.86 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O), 4.02 (s, 3H, CH3O), 3.99 (s, 3H, CH3O); ESI-HRMS: Calcd. for C23H21O6 393.1338; found 393.1345 [M+H]+. 3e: Pale yellow needles; mp 204-206℃; 1H NMR (300 MHz, CDCl3): δ 8.32 (d, 1H, J = 9.3 Hz), 8.13 (d, 1H, J = 9.0 Hz), 8.07 (d, 1H, J = 9.0 Hz), 7.94 (d, 2H, J = 8.4 Hz), 7.55 (d, 2H, J = 8.4 Hz), 7.46 (d, 1H, J = 9.3 Hz), 6.91 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H16O4 367.0737; found 367.0728 [M+H]+. 3f: Light yellow needles; mp 193-195℃; 1H NMR (300 MHz, CDCl3): δ 8.31 (d, 1H, J = 9.0 Hz), 8.16 (d, 1H, J = 9.0 Hz), 8.08 (d, 1H, J = 9.0 Hz), 7.70 (m, 1H, H-C(6')), 7.59 (d, 1H, J = 7.2 Hz, H-C(3')), 7.48 (m, 2H, H-C(40), H-C(5')), 7.41 (d, 1H, J = 9.0 Hz), 6.79 (s, 1H, H-C(3)), 4.05 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H16O4 367.0737; found 367.0733 [M+H]+. 3g: Light yellow needles; mp 194-195℃; 1H NMR (300 MHz, CDCl3): δ 8.32 (d, 1H, J = 9.0 Hz), 8.12 (d, 1H, J = 9.0 Hz), 8.06 (d, 1H, J = 9.0 Hz), 7.98 (s, 1H, H-C(2')), 7.85 (d, 1H, J = 6.6 Hz), 7.53 (m, 2H), 7.47 (d, 1H, J = 9.0 Hz), 6.91 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H16O4 367.0737; found 367.0726 [M+H]+. 3 h: Pale yellow needles; mp 206-208℃; 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J = 9.0 Hz), 8.13 (d, 1H, J = 9.0 Hz), 8.07 (d, 1H, J = 9.0 Hz), 8.01 (m, 2H), 7.46 (d, 1H, J = 9.0 Hz), 7.27 (m, 2H), 6.88 (s, 1H, HC(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H16FO4 351.1033; found 351.1024 [M+H]+. 3i: Pale yellow crystals; mp 192-193℃; 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J = 9.0 Hz), 8.14 (d, 1H, J = 9.0 Hz), 8.07 (d, 1H, J = 9.0 Hz), 8.00 (m, 1H, H-C(6')), 7.55 (m, 1H), 7.45 (d, 1H, J = 9.0 Hz), 7.38 (m, 1H), 7.28 (m, 1H), 7.04 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESIHRMS: Calcd. for C21H16FO4 351.1033; found 351.1045 [M+H]+. 3j: Light yellow crystals; mp 192-194℃; 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J = 9.0 Hz), 8.12 (d, 1H, J = 9.0 Hz), 8.06 (d, 1H, J = 9.0 Hz), 7.76 (d, 1H, J = 7.5 Hz, H-C(60)), 7.73 (m, 1H), 7.55 (m, 1H), 7.47 (d, 1H, J = 9.0 Hz), 7.27 (m, 1H), 6.93 (s, 1H, H-C(3)), 4.07 (s, 3H, CH3O), 4.03 (s, 3H, CH3O); ESI-HRMS: Calcd. for C21H16FO4 351.1033; found 351.1020 [M+H]+.

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  • 发布日期:  2013-01-29
  • 收稿日期:  2012-11-19
  • 网络出版日期:  2012-12-27
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