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Pentacyclic triterpenoid compounds, preparation method thereof, and application of compounds to prepare medicines controlling tumors

A technology of pentacyclic triterpenoids and tumor drugs, which is applied in the direction of antineoplastic drugs, steroids, drug combinations, etc., can solve the problems of low efficiency, poor selectivity, and large toxic and side effects of malignant tumors, and achieve strong selectivity and inhibition Effects on proliferation, inhibition of angiogenesis and metastasis

Inactive Publication Date: 2015-04-22
LIAONING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the treatment of malignant tumors, there are still problems such as low efficiency, poor selectivity, and large toxic and side effects.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0030] Pentacyclic triterpenoids 3β- of the present invention O - S -The preparation method of phenyl-L-cysteinyl oleanolic acid methyl ester, the steps are as follows:

[0031] With oleanolic acid as the starting material, in DMF solvent, K 2 CO 3 with CH 3 I reaction obtains the product of C-28 carboxyl methyl esterification, is catalyst at DMAP, and EDCI is under dehydrating agent condition and protected with amino S -Phenyl-L-cysteine ​​for coupling, finally with CH 2 Cl 2 as solvent, Et 2 Removal of Fmoc Protecting Group under NH Condition to Obtain Oleanolic Acid S - phenyl-L-cysteine ​​conjugates;

[0032] The synthetic route is as follows:

[0033] .

[0034] Pentacyclic triterpenoids 3β- of the present invention O-S - the preparation method of phenyl-L-cysteinyl glycyrrhetinic acid methyl ester, the steps are as follows:

[0035] Firstly methylate the C-30 position of glycyrrhetinic acid, and then use CH 2 Cl 2 As a solvent, under the action of DMAP a...

Embodiment 1

[0041] Example 1: Compound 3β- O - S - Preparation of phenyl-L-cysteinyl oleanolic acid methyl ester

[0042] In a 250mL round bottom flask, add oleanolic acid (5g, 11mmol) and anhydrous K 2 CO 3 (3.78g, 27.35mmol), then add dry DMF (50mL), slowly drop CH under stirring 3I (1.37mL, 21.89mmol), stirred at room temperature for 6 hours, diluted with water after the reaction was completed, washed with 1M hydrochloric acid until slightly acidic, then washed with water until neutral, and washed with saturated sodium chloride, the obtained organic phase was washed with anhydrous Dry over magnesium sulfate, filter, and distill off the solvent under reduced pressure to obtain a crude product, then use ethyl acetate / petroleum ether (1:5, v:v) as eluent for pressurized column chromatography, and separate to obtain white solid olean acid methyl ester. Yield: 5g, yield: 97%, melting point: 197-198°C; IR(KBr): 3348, 2948, 1728, 1426cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): 5.27(t, J =3....

Embodiment 2

[0045] Example 2: Compound 3β- O-S -Preparation of phenyl-L-cysteinyl glycyrrhetinic acid methyl ester

[0046] Glycyrrhetinic acid (1 g, 2.13 mmol) and anhydrous K were added to a 250 mL round bottom flask 2 CO 3 (0.735g, 5.32mmol), then add dry DMF (10mL), add CH dropwise under stirring 3 I (0.26mL, 4.25mmol), stirred at room temperature for 6h, after the reaction was completed, washed with water (20mL×3), extracted the organic phase with ethyl acetate (50ml), washed with saturated NaCl solution, and then anhydrous MgSO 4 Drying, filtration, distillation under reduced pressure, and column chromatography ethyl acetate / petroleum ether (1:2, v:v) gave methyl glycyrrhetinate as a white solid. Yield: 875.2mg, yield: 85.6%, melting point: 240.5-241.8℃; IR(KBr): 3453, 2945, 1723, 1662cm -1 ; 1 H NMR (400MHz, CDCl 3 ): δ 5.65(s, 1H, H-12), 3.68(s, 3H, -OCH 3 ), 3.24-3.21(m, 1H, H-3), 2.79(dt, J 1 =13.2Hz, J 2 =3.6Hz, 1H, H-18), 2.34(s, 1H, H-9), 1.36, 1.15, 1.14, 1....

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Abstract

The invention discloses a kind of pentacyclic triterpenoid compounds, a preparation method thereof, and application of the compounds to prepare medicines controlling tumors. The structural formula of the compounds is shown in the specification, and in the structural formula, R1 is S-phenyl-L-cysteinyl, R2 is hydrogen or carbonyl, and R3 and R4 are selected from COOH, -CH3 and -COOCH3. The pentacyclic triterpenoid compounds have the advantages of being efficient, low in toxicity, high in selectivity and high in specificity.

Description

technical field [0001] The invention relates to the fields of organic chemistry and biochemistry, in particular to a class of pentacyclic triterpenes S - Preparation methods and uses of phenyl-L-cysteine ​​conjugates. The present invention is effective against five kinds of human tumor cell lines cultured in vitro, namely, human lung cancer A549 cell line, human breast cancer MCF-7 cell line, human cervical cancer Hela cell line, human liver cancer HepG2 cell line, and human glioma U87 cell line. The strains were screened for cytostatic activity. The series of compounds of the present invention are found to have a certain activity of inhibiting tumor cell growth, and can be expected to be used as antitumor drugs. Background technique [0002] Cancer is considered to be the "number one killer" of human beings and is called an "incurable disease". Conquering cancer has always been a hot topic all over the world. In developed countries, cancer ranks second among the common ...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61P35/00
CPCC07J63/008
Inventor 赵春晖赵龙铉
Owner LIAONING NORMAL UNIVERSITY
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