Gambogic acid ester derivative as well as preparation method and use thereof
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A technology of gambogic acid and its derivatives, which is applied in the field of gambogic acid ester derivatives and their preparation, can solve the problems of adverse reactions and large immunosuppression, and achieve the effect of easy absorption, broad-spectrum anti-tumor activity, and stable chemical structure
Inactive Publication Date: 2013-06-19
DONGHUA UNIV
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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.
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Embodiment 1
[0041] Synthesis of SZY-182
[0042] Under nitrogen protection, gambogic acid (500mg, 0.71mmol), gemcitabine (169mg, 0.64mmol) and triphenylphosphine (555mg, 2.13mmol) were dissolved in anhydrous tetrahydrofuran (5.0mL), cooled to 0°C for 10 minutes Inject a solution of DEAD (321mg, 2.13mmol) in 5ml THF with a syringe, return to room temperature naturally, and continue the reaction for 12h. Ethyl acetate (50ml) was added to the reactant to quench, then poured into saturated brine (3×10ml) for washing, dried over anhydrous sodium sulfate, and evaporated to remove ethyl acetate. Column chromatography [V (methanol): V (dichloromethane) = 3: 100] gave 294 mg of an orange-yellow amorphous powder with a yield of 47.4%. 1 H NMR (CDCl 3,400MHz)δ:12.87(s,1H,6-OH),7.58(d,J=6.88Hz,1H,10-H),6.68(d,J=10.12Hz,1H,4-H),6.38( m, 1H, 1”-H), 6.14~6.18(m, 1H, 27-H), 5.87(d, J=6.96, 2H, 5’-H, 6’-H), 5.40(d, J= 10Hz, 1H, 3-H), 5.06~5.08(m, 1H, 32-H, 37-H), 4.18(m, 1H, 4”-H), 4.08(m, 1H, 5”-H), ...
Embodiment 2
[0044] In vitro anti-tumor activity test
[0045] 1. Experimental cell line:
[0046] The tumor cell lines used in this experiment are: A549 (human lung adenocarcinoma cells), HCT116 (human colon cancer cells), PANC-1 (human pancreatic cancer cells) and HepG2 (human liver cancer cells) (provided by Shanghai Institute of Pharmaceutical Industry pharmacology laboratory cryopreservation and passage).
[0047] 2. Sample preparation:
[0048] After dissolving with DMSO (Merck), add PBS(-) to make a 1000μg / ml solution or a homogeneous suspension, and then dilute with DMSO-containing PBS(-). The positive control drug was gambogic acid.
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Abstract
The invention relates to a gambogic acid ester derivative as well as a preparation method and a use thereof. The structural formula of the derivative is as shown in formula (I) in the specification. The preparation method of the gambogic acid ester derivative comprises the following steps of: dissolving gambogic acid, gemcitabine and triphenylphosphine in anhydrous tetrahydrofuran under the protection of nitrogen gas; injecting a THF (Tetrahydrofuran) solution containing Diethyl Azodicarboxylate (DEAD) and reacting for 12-24 hours; and obtaining a product by washing, drying, rotary steaming and column chromatography. The derivative can be used for preparing a composition, an antineoplastic drug, an antifungal drug or an anti-angiogenic drug or is combined with other anti-cancer active components. The derivative disclosed by the invention not only has good activity to a plurality of tumor cells, but also has good targeting performance to the tumor cells, and therefore, a foundation is laid for developing novel drugs.
Description
technical field [0001] The invention belongs to the field of natural product derivatives of traditional Chinese medicine, and in particular relates to a gambogic acid ester derivative and its preparation method and application. Background technique [0002] Malignant tumors are one of the major diseases that seriously threaten human life and quality of life. At present, most antineoplastic drugs are synthetic drugs, which have the disadvantages of large adverse reactions and immunosuppression. Therefore, finding new anticancer drugs and methods, reducing adverse reactions of chemotherapy, and improving the quality of life of patients has become a hot spot in medical research. Because of their ability to inhibit tumor growth and have less toxic and side effects, traditional Chinese medicines and herbal medicines have received widespread attention from medical workers. [0003] Gambogic acid is a compound with high anti-tumor activity and good cell selectivity extracted from ...
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