A macrocyclic oxidation substituted pentacyclic triterpanoids derivative and preparation method and use thereof
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A technology of pentacyclic triterpenoids and compounds, which is applied in the field of organic chemistry and medicinal chemistry, and can solve problems such as research in the ascendant
Inactive Publication Date: 2008-02-06
ZHEJIANG HISUN PHARMA CO LTD
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Embodiment 1
[0038] Embodiment 1: the preparation of compound Ig
[0039]Under ice-salt bath, ursolic acid (1.0 mmol) was dissolved in 10 ml of dichloromethane, 6 ml of triethylamine was added, and methanesulfonyl chloride (16.3 mmol) was added dropwise at 0°C. Stir at room temperature for 4 hours. After filtering, the filtrate was washed with 5 ml of 1 mol / L hydrochloric acid solution, washed with water until neutral, and dried over anhydrous magnesium sulfate. Precipitation under reduced pressure gave 3β-methylsulfonyloxy-arbutane-28-acid-12-ene. Dissolve in 10 ml of acetic acid (containing 0.5 ml of acetic anhydride), add chromium trioxide (4.0 mmol), and stir overnight at room temperature. 10 ml of water and 10 ml of dichloromethane were added to the reaction solution, and the layers were separated, and the aqueous layer was extracted with 10 ml of dichloromethane. The organic layers were combined, washed with 10 ml of saturated sodium bicarbonate solution, washed with water until n...
Embodiment 2～ Embodiment 9
[0042] According to the method of Example 1, the compounds of Example 2 to Example 9 shown below were prepared
Embodiment 2
[0043] Example 2: Preparation of 11-carbonyl-arbutane-28-acid-2,12-diene (Ia), C 30 h 44 o 3 , MS: ESI m / e 452 (M + ); Rf[(petroleum ether / ethyl acetate: 3 / 1)+1%HCOOH]: 0.60; 1 HNMR (400MHz) δ: 0.87(d, 3H, J=6.0Hz), 0.97(d, 3H, J=6.4Hz), 5.36(dd, 1H, J=2.0, 10.0Hz, H-3), 5.43( dd, 1H, J=5.6, 10.0 Hz, H-2), 5.62 (s, 1H, H-12).
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Abstract
The present invention relates to a pentacyclic triterpanoid derivative of multiple-oxide substitution of the A ring and the medicine salt or solvate of the derivative, and the present invention also relates to the preparation method, the drug combination, and medical use of the derivative. The compound of the present invention has the functions of inhibiting the activity of six human tumor cell strains in vitro, such as human prostate cancer cell (PC-3), nasopharyngeal carcinoma cells (CNE), oral squamous carcinoma cell(KB), human lung cancer cell (A549), human hepatoma cell (BEL-7404), and human cervix cancer cell (Hela), and the function of the invention is at the same magnitude of the positive control of cisplatin, thereby the compound can be used as expected antitumor drug. The compound of the present invention also inhibits the alpha glucosidase strongly, and the inhibiting effect is greater than the positive control of acarbose, thereby the compound can be used as expected medicine for preventing and treating diabetes and the treatment of the virus diseases.
Description
technical field [0001] The invention relates to the fields of organic chemistry and medicinal chemistry, in particular, the invention relates to pentacyclic triterpene derivatives substituted by polyoxygenation of the A ring, a preparation method and application thereof. The present invention treats the series of compounds on six tumor cell lines such as human prostate cancer cell (PC-3), nasopharyngeal carcinoma cell (CNE), oral cavity epithelial cancer cell (KB), human lung cancer cell (A549), human liver cancer cell ( BEL-7404), human cervical cancer cells (Hela) were screened for tumor cell growth inhibitory activity. The compounds are found to have a certain activity of inhibiting the growth of tumor cells, and can be expected to be used as antitumor drugs. The present invention also finds that such compounds have a strong inhibitory effect on α-glucosidase, and can be expected to be used as medicines for preventing and treating diabetes and treating viral diseases. Ba...
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