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1,3-Dihydroxyxanthone derivatives and their use in medicine

A technology of hydroxyxanthone and its derivatives, which is applied in the application field of 1,3-dihydroxyxanthone derivatives in the treatment of malignant tumors, and can solve unseen problems

Active Publication Date: 2018-10-16
哈尔滨医大药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] So far, there have been no 1,3-dihydroxyxanthone derivatives containing a pinionamide pharmacophore and their application in medicine

Method used

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  • 1,3-Dihydroxyxanthone derivatives and their use in medicine
  • 1,3-Dihydroxyxanthone derivatives and their use in medicine
  • 1,3-Dihydroxyxanthone derivatives and their use in medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Compound ZDBB-1 preparation of

[0021] The synthetic route is as follows:

[0022]

[0023] The synthetic route of intermediate 1 can be found in reference (Varache-Lembege, et al, European Journal of Medicinal Chemistry, 2008, 43, 1336-1343.).

[0024]

[0025] The synthetic route of compound ZDBB-1 can be found in the reference (Shoujiao Peng et al, J.Med.Chem.2015,58, 5242-5255).

[0026] Add raw material 110mmol, intermediate 210mmol, CH 2 Cl 2 10ml, 10ml of triethylamine, stirred at room temperature for 10h. Then add saturated NH 4 Washed with Cl solution, CH 2 Cl 2 Extraction, washing with saturated brine, MgSO 4 Dried and concentrated. The crude product was separated by column chromatography with a yield of 75%.

[0027] 1 H NMR (400MHz, DMSO): δ12.90(s, 1H), 9.86(s, 1H), 8.24–8.20(m, 1H), 7.87(d, J= 15.6Hz, 1H), 7.86–7.84(m ,1H),7.54–7.52(m,1H),7.48–7.44(m,1H),7.35(d,J=15.6Hz,1H),6.95-6.90(m,1H),6.24(d,J=2.4 Hz, 1H), 6.04(t, J=9.6...

Embodiment 2

[0029] Embodiment 2: compound ZDBB-2 preparation of

[0030] The synthetic route is the same as that of compound ZDBB-1.

[0031] The yield of compound ZDBB-2 was 70%.

[0032] 1 H NMR (400MHz, DMSO): δ12.94(s, 1H), 9.89(s, 1H), 8.26–8.22(m, 1H), 7.84(d, J= 15.6Hz, 1H), 7.86–7.85(m ,1H),7.56–7.54(m,1H),7.46–7.42(m,1H),7.32(d,J=15.6Hz,1H),6.94-6.92(m,1H),6.02(t,J=9.6 Hz, 1H), 4.04 (t, J = 6.4Hz, 2H), 3.88 (s, 3H), 2.42 (m, 2H).

[0033] MS-ESI (m / z): 407.1.

Embodiment 3

[0034] Embodiment 3: compound ZDBB-3 preparation of

[0035] The synthetic route is the same as that of compound ZDBB-1.

[0036] The yield of compound ZDBB-3 was 65%.

[0037] 1 H NMR (400MHz, DMSO): δ12.98(s, 1H), 9.87(s, 1H), 8.24–8.22(m, 1H), 7.86(d, J= 15.6Hz, 1H), 7.84–7.82(m ,1H),7.57–7.55(m,1H),7.44–7.42(m,1H),7.36(d,J=15.6Hz,1H),6.97-6.95(m,1H),6.04(t,J=9.6 Hz, 1H), 4.00 (t, J=6.4Hz, 2H), 2.42 (m, 2H), 2.34 (s, 3H).

[0038] MS-ESI (m / z): 391.1.

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Abstract

The invention relates to the field of medicines and discloses a novel 1,3-dyhydroxylxanthone derivative and application thereof in medicines. The general formula of the novel 1,3-dyhydroxylxanthone derivative is as shown in Figure (I). It is proved that the novel 1,3-dyhydroxylxanthone derivative has good anti-tumor activity and a new choice is provided for preparation of anti-tumor drugs by determining the activity inhibiting effect on malignant tumor cells of the novel 1,3-dyhydroxylxanthone derivative.

Description

technical field [0001] The invention relates to a class of 1,3-dihydroxyxanthone derivatives and their application in medicine, in particular to the application of 1,3-dihydroxyxanthone derivatives in treating malignant tumors. Background technique [0002] Tumor, namely cancer, is a common and frequently-occurring disease that seriously threatens human health, and the death caused by it has ranked first among all causes of death. The treatment of malignant tumors has become a major scientific research topic in the field of medicine all over the world. [0003] Xanthone compounds (Xanthone, whose structure is shown in the figure) have a wide range of physiological activities. The research reports on the antitumor activity of xanthone compounds can be traced back to 1972, when the xanthone compound akronin was found to have antitumor activity in vivo. Subsequently, new xanthone derivatives have been found to have good inhibitory effects on a variety of tumor cells, includin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06A61P35/00A61P35/02
CPCC07D405/06
Inventor 金加明
Owner 哈尔滨医大药业股份有限公司