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 l

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
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Example Embodiment

[0019] Example 1 Synthesis of Compound 1

[0020]

[0021] Dissolve 50mg 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 slightly acidic, and fully extract with ethyl acetate; use the organic phase Wash with saturated brine, anhydrous Na 2 SO 4 After drying, concentration, and column chromatography, 45 mg of compound 1 was obtained, 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 = 5.9 Hz), 4.69 (2H, 3-OCH 2 OCH 3 , S), 4.68 (1H, 12-OCH 2 OCH 3 , AB, J = 5.9 Hz), 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 = 7.8 Hz), 2.36 (1H, 15-H, m), 1.28 (3H, 21-H, d, J = 8.0 Hz), 0.93 (3H , 18-H, s),...

Example Embodiment

[0030] Example 2 Synthesis of Compound 2

[0031]

[0032] Dissolve 50mg (0.12mmol) of compound 5 in 5ml acetone and add 0.05ml H 2 SO 4 , 20mg CrO 3 (0.2mmol) and 1ml of water to prepare an oxidant, then warmed to room temperature and stirred for reaction, followed by TLC until the reaction was completed. Remove the solid by suction filtration, use CH 2 Cl 2 Wash several times, use plenty of water and saturated NaHCO for the filtrate 3 The solution and saturated brine were washed to neutrality, dried over anhydrous magnesium sulfate, concentrated, and flash column chromatography to obtain compound 2 13mg, 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=8.0 Hz, 3H, 21-H), 1.30 (3H, s, 18-H), 0.75 (3H, 19-H, s);

[0036] IR(γmax, cm -1 ): 3512, 2926, 2858, 1767, 1737, 1448, 1377, 1248, 1035, 961, 885;

[0037] EIMS(m / z): 405...

Example Embodiment

[0042] Example 3 Synthesis of Compound 3

[0043]

[0044] In a 50 mL three-necked flask, 628 mg of epoxy acid 6 (1.68 mmol) and 15 mL of absolute ethanol were added and stirred to dissolve. Add 710mg LiOH·H 2 O(16.8mmol), add 5 mL of 30% hydrogen peroxide dropwise, stir and gradually raise the temperature to 80℃ to react for ~24h (add H in the middle 2 O 2 2mL), TLC tracking (2:1 n-C 6 H 14 -AcOEt expand). After the reaction is completed (the intermediate product-diol is generated at this time), use saturated NaHSO 3 Remove excess hydrogen peroxide and add saturated NH 4 The Cl aqueous 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. The crude oily product obtained was separated b...

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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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