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C17-hydroxy-steroid lactone antitumour medicine

An anti-tumor drug and anti-tumor technology, applied in the direction of anti-tumor drugs, drug combinations, steroids, etc., to achieve the effect of simple synthesis method

Inactive Publication Date: 2006-03-29
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the biological activity of 17-hydroxysteroid lactone compounds has not been reported in the literature

Method used

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  • C17-hydroxy-steroid lactone antitumour medicine
  • C17-hydroxy-steroid lactone antitumour medicine
  • C17-hydroxy-steroid lactone antitumour medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The synthesis of embodiment 1 compound 1

[0020]

[0021] Dissolve 50mg of compound 4 and 45mg (10eq) LiOH in a mixed solution of hydrogen peroxide (30%) and ethanol, react in an oil bath at 40°C until the raw materials disappear; neutralize dilute hydrochloric acid to partial acidity, and fully extract with ethyl acetate; use Washed with saturated brine, anhydrous Na 2 SO 4 Drying, concentration, and column chromatography yielded 45 mg of compound 1, Yield: 90%.

[0022] Compound 1 data:

[0023] C 26 h 42 o 7 466;

[0024] 1 HNMR (CD 3 COCD 3 ): 4.78 (1H, 12-OCH 2 OCH 3 , AB, J=5.9Hz), 4.69 (2H, 3-OCH 2 OCH 3 , s), 4.68 (1H, 12-OCH 2 OCH 3 , AB, J=5.9Hz), 4.58 (1H, 16-H, d-d, J 1 =7.8Hz,J 2 =5.0Hz), 3.937 (1H, 12-H, d-d, J 1 =10.8Hz,J 2 =5.0Hz), 3.55(1H, 3-H, m), 3.40(3H, 12-OCH 2 OCH 3 , s), 3.35 (3H, 3-OCH 2 OCH 3 , s), 2.88(1H, 20-H, q, J=7.8Hz), 2.36(1H, 15-H, m), 1.28(3H, 21-H, d, J=8.0Hz), 0.93(3H , 18-H, s), 0.87...

Embodiment 2

[0030] The synthesis of embodiment 2 compound 2

[0031]

[0032] Dissolve 50 mg (0.12 mmol) of compound 5 in 5 ml of acetone, add 0.05 ml of H 2 SO 4 , 20mg CrO 3 (0.2mmol) and 1ml of water were prepared as an oxidizing agent, then raised to room temperature and stirred for reaction, followed by TLC until the end of the reaction. The solid was removed by suction filtration, and the 2 Cl 2 Washed several times, the filtrate was washed with a large amount of water, saturated NaHCO 3 The solution was washed with saturated brine until neutral, dried over anhydrous magnesium sulfate, concentrated, and subjected to flash column chromatography to obtain 13 mg of compound 2, Yield: 26%.

[0033] Compound 2 data:

[0034] C 24 h 36 o 5 404;

[0035] 1 HNMR (CDCl3): 4.70 (m, 1H, 3-H), 4.40 (m, 1H, 16-H), 2.40 (m, 1H, 20-H), 2.00 (s, 3H, CH 3 CO), 1.40(d, J=8.0Hz, 3H, 21-H), 1.30(3H, s, 18-H), 0.75(3H, 19-H, s);

[0036] IR(γmax, cm -1 ): 3512, 2...

Embodiment 3

[0042] The synthesis of embodiment 3 compound 3

[0043]

[0044] In a 50 mL three-necked flask, add 628 mg of epoxy acid 6 (1.68 mmol) and 15 mL of absolute ethanol, and stir to dissolve. Add 710mg LiOH·H 2 O (16.8mmol), add 5mL of 30% hydrogen peroxide dropwise, stir and gradually raise the temperature to 80°C and react for ~24h (additional H 2 o 2 2mL), TLC tracking (2:1 n-C 6 h 14 -AcOEt expansion). After the reaction was completed (at this moment, what was generated was an intermediate product—diol), and saturated NaHSO 3 Remove excess hydrogen peroxide, add saturated NH 4 The aqueous Cl solution was neutralized to acidity, the organic phase was separated, and the aqueous phase was extracted once with 100 mL of ethyl acetate. The organic phase was washed twice with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was recovered under reduced pressure, and the obtained oily crude...

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PUM

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Abstract

An anticancer 17-hydroxy-steroid lactone medicine for treating lung cancer, breast cancer, liver cancer, leukemia, etc is disclosed. Its advantages are simple preparing process and high suppression activity to A-549, MCF-7, BEL-7402 and P388.

Description

technical field [0001] This patent relates to the antitumor application of a class of 17-hydroxy-steroid lactone. Such compounds can be conveniently synthesized by chemical methods, and they have been shown to have anticancer activity and are an antitumor drug. Background technique [0002] Steroidal compounds with 17-hydroxyl have unique biological activity and medicinal value, such as marine natural product pyrazine bisteroid (Cephalostatine) (see J.Chem.Soc., Chem..Commun., 1988,865; ibid, 1988, 1440), the natural product Pannifolia saponin (OSW-1) (see Bioorg. See Journal of Pharmaceutical Analysis, 1997, 17, 153; Journal of Pharmaceutical Analysis, 1991, 11, 90; Journal of China Pharmaceutical University, 1989, 20, 251). [0003] [0004] Tian Weisheng and others have long been committed to the rational utilization of resource compounds, especially the rational utilization of steroidal sapogenins. They have developed a clean method for degrading steroidal sapogenin...

Claims

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Application Information

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IPC IPC(8): C07J71/00A61P35/00
Inventor 田伟生兰泉许启海
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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