Gambogic acid derivative, preparation method and uses thereof

A derivative, the technology of gambogic acid, applied in the field of natural product derivatives of traditional Chinese medicine, can solve the problems of adverse reactions and immunosuppression, and achieve the effect of balancing water solubility and fat solubility, stabilizing chemical structure, and improving fat solubility

Active Publication Date: 2013-10-16
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, most antineoplastic drugs are synthetic drugs, which have the disadvantages of large adverse reactions and immunosuppression. Therefore, it has become a hot spot in medical research to find new anticancer drugs and methods, reduce adverse reactions of chemotherapy, and improve the quality of life of patients.

Method used

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  • Gambogic acid derivative, preparation method and uses thereof
  • Gambogic acid derivative, preparation method and uses thereof
  • Gambogic acid derivative, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of WMQ-22

[0037] (1) In a 50ml reaction flask, add 500mg of p-aminobenzoic acid and 20ml of methanol, stir to dissolve, and then slowly add 5ml of SOCl in an ice-water bath. 2 , Install CaCl 2 Dry the tube and react for 3 hours. Then spin dry the solvent, wash repeatedly with distilled water to remove too much unreacted SOCl 2 Wash it off and dry it to obtain methyl para-aminobenzoate hydrochloride.

[0038] (2) In another 50ml reaction flask, add 1.873g of gambogic acid and 10ml of anhydrous dichloromethane and stir together, then add 610mg EDCI, 429mg HOBT, 1g DIEA at room temperature, and finally add 640mg p-aminomethyl benzoate Ester hydrochloride, install a drying tube, stir and react at room temperature for 4 hours. Detection by TCL showed that the reaction was complete. The reaction was quenched with 60 ml of ethyl acetate and washed with saturated brine three times to obtain the crude product of the title compound. The crude product was separated with e...

Embodiment 2

[0041] Synthesis of WMQ-29

[0042] (1) In a 50ml reaction flask, add p-chloromethylbenzoic acid and 10ml ethanol, stir to dissolve, and then slowly add 2ml SOCl dropwise in an ice-water bath 2 , Install CaCl 2 Dry the tube and react for 3 hours. Then spin dry the solvent, wash repeatedly with distilled water to remove too much unreacted SOCl 2 Wash it off and dry it to obtain ethyl p-chloromethyl benzoate.

[0043] (2) In another 50ml reaction flask, add 500mg of gambogic acid and 10ml of anhydrous dichloromethane and stir together, then add sodium bicarbonate powder and methyl p-chloromethyl benzoate at room temperature, install a drying tube, Stir overnight at room temperature. Detection with TCL showed that the reaction was complete. The reaction was quenched with 50ml of dichloromethane and washed twice with 10ml of saturated sodium bicarbonate solution. Then, it was washed three times with saturated brine to obtain a crude product of the title compound. The crude product w...

Embodiment 3

[0050] In vitro anti-tumor activity test

[0051] 1. Experimental cell line:

[0052] The tumor cell lines used in this experiment are: A549 (human lung adenocarcinoma cells), HCT116 (human colon cancer cells), ZR-75-30 (human breast cancer cells) and HepG2 (human liver cancer cells) (by Shanghai Pharmaceutical Industry Cryopreservation and passage in the Pharmacology Laboratory of the Institute).

[0053] 2. Sample preparation:

[0054] After dissolving with DMSO (Merck), add PBS(-) to make a 1000μg / ml solution or uniform suspension, and then dilute with PBS(-) containing DMSO. The positive control drug is gambogic acid.

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Abstract

The present invention relates to a gambogic acid derivative, a preparation method and uses thereof. The structure formula of the derivative is represented by a formula (I). The preparation method comprises: in an inert solvent, carrying out a reaction of gambogic acid and p-aminomethyl benzoate (formula (III)) or chloromethyl benzoate. The gambogic acid derivative can be used for preparing compositions, anti-tumor drugs, antifungal drugs or anti-angiogenesis drugs, or combining with other anti-cancer active ingredients to be used. In addition, the gambogic acid derivative provides good activity for plural types of tumor cells, and presents good tumor cell targeting performances so as to establish a foundation for development of novel drugs.

Description

Technical field [0001] The invention belongs to the field of natural product derivatives of traditional Chinese medicine, and specifically relates to a gambogic acid derivative and a preparation method and application thereof. Background technique [0002] Malignant tumors are one of the major diseases that seriously threaten human life and quality of life. At present, most anti-tumor drugs are synthetic drugs, which have large adverse reactions and immunosuppression. Therefore, finding new anti-cancer drugs and methods, reducing adverse reactions of chemotherapy, and improving the quality of life of patients has become a hot spot in medical research. Traditional Chinese medicines and botanicals have received general attention from medical workers because of their ability to inhibit tumor growth and have less side effects. [0003] Gambogic acid is a compound extracted from Garcinia Hanburryi (Garcinia Hanburryi) with high anti-tumor activity and good cell selectivity. Experiment...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20A61P35/00A61P31/12
Inventor 邵志宇孙中强吴孟强宋云龙赵圣印邓云霞
Owner DONGHUA UNIV
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