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Tripteryglide cinnamate derivatives and preparation method and use thereof

A technology of tripterine and cinnamate, which is applied in the direction of pharmaceutical formulations, drug combinations, steroids, etc., and can solve the problems that the activity needs to be improved

Active Publication Date: 2022-03-08
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Based on the above, although tripterine has clear anti-tumor activity, its activity still needs to be improved.

Method used

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  • Tripteryglide cinnamate derivatives and preparation method and use thereof
  • Tripteryglide cinnamate derivatives and preparation method and use thereof
  • Tripteryglide cinnamate derivatives and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the preparation of intermediate II-1

[0039] 2-Bromoethanol (1mM, 1eq, 70.9μl) was dissolved in 6mL of DCM, and cinnamic acid (1.2mM, 1.2eq, 177.6mg), EDCI (1.5mM, 1.5eq, 287.6mg) and DMAP ( 0.5mM, 0.5eq, 61.1mg), stirred at room temperature for 7 hours, concentrated under reduced pressure and dissolved in DCM, followed by 5% NaHCO 3 The organic layer was washed with aqueous solution and saturated NaCl solution, dried over anhydrous sodium sulfate, spin-dried, and purified by silica gel column chromatography (PE / EA=16:1) to obtain 137.2 mg of white solid with a yield of 54%.

[0040] ESI-MS: Bromine isotope characteristic peaks 255.0, 257.0 [M+H] + .

[0041] The reaction formula is as follows:

[0042]

Embodiment 2

[0043] Embodiment 2: the synthesis of I-1

[0044] Dissolve 45.0mg (0.1mM, 1.0eq) tripterine in 2ml DMF, add 42.0mg NaHCO 3 (0.5mM, 5.0eq), stirred for 7h, added 76.2mg (0.3mM, 3.0eq) of intermediate II-1, and heated to reflux at 60°C. Until TLC detection shows that the reaction is complete, add 50ml CH 2 Cl 2 Dilute, extract with water, discard the aqueous layer, wash the organic layer with saturated NaCl, dry over anhydrous sodium sulfate, filter with suction, evaporate the solvent to dryness, and purify by column chromatography (PE / EA=6:1) to obtain 34.3mg, yield 55 %.

[0045] ESI-MS: 647.3 [M+Na] + .

[0046] 1 H-NMR (300MHz, CDCl 3 , TMS), δppm: 0.58(3H,s), 1.11(3H,s), 1.22(3H,s), 1.26(3H,s), 1.43(3H,s), 2.21(3H,s), 4.08- 4.12(1H,m),4.30-4.46(3H,m),6.26(1H,d,J=7.1Hz),6.44(1H,d,J=16.0Hz),6.52(1H,s),6.95(1H ,d,J=7.1Hz),7.43(3H,m),7.55(2H,m),7.72(1H,d,J=16.1Hz).

[0047]

Embodiment 3

[0048] Embodiment 3: the preparation of intermediate II-2

[0049] The 2-bromoethanol in Example 1 was replaced with 3-bromo-1-propanol (1mM, 1eq, 90.4μl), and other conditions remained unchanged, to obtain 141.5mg of white solid II-2 with a yield of 52.8%.

[0050] ESI-MS: Bromine isotope characteristic peaks 269.0, 271.0 [M+H] + .

[0051] The reaction formula is as follows:

[0052]

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Abstract

The invention discloses a tripterine cinnamate derivative represented by formula I, and discloses a preparation method thereof. The invention also discloses a pharmaceutical composition using the above-mentioned tripteryne cinnamate derivatives as active ingredients, and the use of the tripteryne cinnamate derivatives and the pharmaceutical composition in preparing antitumor drugs.

Description

technical field [0001] The invention relates to medicinal chemistry technology, in particular to a tripterine derivative and its preparation method and application. [0002] technical background [0003] Malignant tumors are one of the diseases that seriously threaten human life and health. The incidence and mortality of this disease are increasing all over the world. Among them, China has become the hardest hit area, and the burden of malignant tumors cannot be ignored. In addition, cancer has brought huge economic losses to the world and is the world's top "economic killer". Therefore, the prevention and treatment of cancer has become the focus of research in the field of medicine. [0004] Currently, chemotherapy is one of the main means of tumor treatment. Chemotherapy drugs have cytotoxic effect and can inhibit the growth and reproduction of tumor cells to kill tumor cells. However, traditional chemotherapeutic drugs are poor in selectivity and easily cause greater ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61K45/06A61P35/00
CPCC07J63/008A61P35/00
Inventor 陈莉李娜徐蔓依陈称雷志超杨念
Owner CHINA PHARM UNIV