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A kind of triptolide derivative and its preparation method and application

A technology of triptolide and derivatives, applied in the field of medicine, can solve problems such as adverse reactions, clinical application limitations, and poor water solubility of triptolide, and achieve the effect of improving water solubility

Active Publication Date: 2021-02-23
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that triptolide is an effective anti-tumor agent, which can inhibit the growth of cancer cells both in vitro and in vivo, but because triptolide has poor water solubility, narrow therapeutic window, and can cause serious adverse reactions, cell High toxicity limits its clinical application

Method used

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  • A kind of triptolide derivative and its preparation method and application
  • A kind of triptolide derivative and its preparation method and application
  • A kind of triptolide derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Preparation of Compound Mito-TP-1

[0050] Add triptolide (0.055mmol, 20mg), 5-bromovaleric acid (0.165mmol, 29.9mg), EDCI (0.22mmol, 42.2mg), DMAP (0.11mmol, 13.4mg) into 2ml of anhydrous dichloromethane , reacted at room temperature under nitrogen protection for 8 hours, and the reaction progress was carried out under TLC detection to obtain a yellow clear solution. Extract three times with saturated sodium bicarbonate solution, remove the lower methylene chloride layer, add an appropriate amount of anhydrous magnesium sulfate to dry for 20 minutes, filter under reduced pressure, and concentrate by rotary evaporation. Use the silica gel preparation plate method (petroleum ether: ethyl acetate = 1:1) to separate and obtain a white solid powder. Take intermediate 1 (0.0382 mmol, 20.0 mg) and dissolve it in 3 mL of acetonitrile, add triphenylphosphine (0.116 mmol, 29.3mg), heated to reflux at 80°C in an oil bath for 48h, TLC detected that the reaction was bas...

Embodiment 2

[0056] Example 2 Preparation of Compound Mito-TP-2

[0057] According to the method of Example 1, intermediate 2 and compound Mito-TP-2 were prepared by selecting raw materials according to the following synthetic route.

[0058] The synthetic route is as follows:

[0059]

[0060] Spectral data:

[0061] Intermediate 2: 1 H NMR (600MHz, CD 3 OD)δ5.08(s,1H,H-14),4.80(m,2H,H-19),3.96(d,J=3.2Hz,1H,H-11),3.63(d,J=3.1Hz ,1H,H-12),3.48(m,2H,H-6'),3.48(m,1H,H-7),2.78(m,1H,H-5),2.48(m,2H,H- 2'),2.27(m,1H,H-2a),2.27(m,1H,H-6a),2.06(m,1H,H-2b),1.85(m,1H,H-15),1.85( m,1H,H-6b),1.85(m,2H,H-5'),1.67(m,2H,H-3'),1.50(m,2H,H-4'),1.50(m,1H ,H-1a),1.33(m,1H,H-1b),1.04(s,3H,H-20),0.95(d,J=7.0Hz,3H,H-17),0.85(d,J= 6.9Hz, 3H, H-16); 13 C NMR (150MHz, CD 3 OD) δ176.18 (C-18), 174.53 (C-1'), 163.98 (C-4), 125.66 (C-3), 72.77 (C-14), 72.12 (C-19), 65.03 (C -13),64.35(C-9),62.85(C-8),61.24(C-7),56.86(C-11),56.35(C-12),41.59(C-5),36.96(C- 10),35.10(C-2'),34.29(C-6'),33.83(C-5'),30.96(C...

Embodiment 3

[0063] Example 3 Preparation of Compound Mito-TP-3

[0064] According to the method of Example 1, intermediate 3 and compound Mito-TP-3 were prepared by selecting raw materials according to the following synthetic route.

[0065] The synthetic route is as follows:

[0066]

[0067] Spectral data:

[0068] Intermediate 3: 1 H NMR (600MHz, CD 3 OD)δ5.08(s,1H,H-14),4.80(m,2H,H-19),3.96(d,J=3.1Hz,1H,H-11),3.63(d,J=2.5Hz ,1H,H-12),3.46(m,2H,H-7'),3.46(m,1H,H-7),2.78(m,1H,H-5),2.45(m,2H,H- 2'),2.27(m,1H,H-2a),2.27(m,1H,H-6a),2.06(m,1H,H-2b),1.85(m,1H,H-15),1.85( m,1H,H-6b),1.85(m,2H,H-6'),1.67(m,2H,H-3'),1.50(m,2H,H-5'),1.50(m,2H ,H-4'),1.50(m,1H,H-1a),1.33(m,1H,H-1b),1.04(s,3H,H-20),0.95(d,J=7.0Hz,3H ,H-17),0.85(d,J=6.9Hz,3H,H-16); 13 C NMR (150MHz, CD 3 OD) δ176.24 (C-18), 174.73 (C-1'), 164.03 (C-4), 125.68 (C-3), 72.78 (C-14), 72.13 (C-19), 65.04 (C -13), 64.36(C-9), 62.83(C-8), 61.26(C-7), 56.85(C-11), 56.39(C-12), 41.61(C-5), 36.98(C- 10),35.22(C-2'),34.42(C-7'...

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Abstract

The present invention provides a triptolide derivative, which has the structure shown in formula I: wherein, n is an integer of 4-10. The triptolide derivatives of the present invention have better selectivity to tumor cells while retaining better anti-tumor activity, lower toxicity to normal cells, and better water solubility, which is beneficial to the development of drugs. The triptolide derivatives of the present invention have the potential to be used as antitumor drugs by absorbing and exerting drug effects in the body and reducing adverse reactions.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a triptolide derivative and its preparation method and application. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] A major problem in cancer treatment is the poor selectivity and high toxicity of chemotherapeutic drugs. Designing drugs based on the differences between tumor cells and normal cells is expected to achieve certain selectivity of anti-tumor drugs. Studies have shown that the mitochondrial membrane potential of tumor cells is much greater than that of normal cells. With the understanding of the functional and structural changes of mitochondria in tumor cells, the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J73/00A61K31/665A61P35/00
CPCA61P35/00C07J73/003
Inventor 范培红宋慧娜
Owner SHANDONG UNIV
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