Diosgenin piperazine derivatives and preparation method thereof

A technology of diosgenin and aglycone piperazine, which is applied in the directions of drug combination, steroids, antitumor drugs, etc.

Inactive Publication Date: 2010-07-28
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Diosgenin piperazine derivatives and preparation method thereof
  • Diosgenin piperazine derivatives and preparation method thereof
  • Diosgenin piperazine derivatives and preparation method thereof

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specific Embodiment approach

[0050] The specific embodiment: enumerate typical compound of the present invention below in conjunction with example

example 1

[0051] The synthesis of example 1 diosgenin loss F ring 27-piperazine compound (1)

[0052]

[0053] 1, the synthesis (I) of diosgenin 3-Ac: get diosgenin (2g, 4.8mmol), acetic anhydride (4ml, 40.2mmol) in pyridine (8ml), after stirring in ice bath for 30 minutes, be heated to 60°C, react for 3 hours. After the reaction was completed, it was cooled to room temperature, and then the reaction solution was poured into ice water (500ml) and stirred for 1 hour, then filtered, and the solid was washed with ice water (50ml*5) and vacuum-dried to obtain a white solid.

[0054]

[0055] 2. Synthesis of diosgenin 3-Ac missing F ring (II): Dissolve compound I (1.5 g) in dichloromethane (8 ml), slowly add glacial acetic acid (20 ml) dropwise at room temperature, and stir for 10 minutes , added sodium cyanoborocyanide (1.060g, 16.51mmol) in batches, after reacting at room temperature for 5 hours, added water (15ml) and stirred for 10 minutes, then extracted with dichloromethane, and t...

example 2

[0061] Example 2 Synthesis of 1-diosgenin lost F ring-4-substituted-piperazine compound (2)

[0062]

[0063] Compound 1 (175mg, 0.35mmol) and benzyl bromide (140mg, 0.82mmol) were dissolved in acetonitrile (15ml), and reacted at 60°C for 5 hours. After the solvent was evaporated under reduced pressure, it was dissolved with dichloromethane (30ml), and the solution was washed twice with saturated sodium bicarbonate solution, once with saturated brine, dried over anhydrous sodium sulfate, and the insoluble matter was filtered out, and the filtrate was spin-dried under reduced pressure, leaving The product was purified by column chromatography to obtain 1-diosgenin lost F ring-4-substituted-piperazine compound (147mg), mp220-221°C, yield: 60.4%.

[0064] 1 HNMR (CDCl3, 400MHz): 7.52-7.49 (dd, J = 13.6HZ, 2); 7.47-7.38 (m, 3H); 5.35-5.34 (t, J = 4.4HZ, 1H); 3.93 (S, 2H)

[0065] 13 CNMRCDCL3,100MHz):δ140.81,133.77,130.78,129.33,128.87,121.34,89.77,83.26,71.66,64.83,63.58,61...

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Abstract

The invention relates to novel diosgenin piperazine compounds, a preparation method thereof and application of a medicinal composition taking the compounds as active ingredients in antitumor aspects. The preparation method comprises the steps of: preparing 1-sterides piperazine compounds from diosgenin and piperazine serving as raw materials; and reacting the 1-sterides piperazine compound with ArX to synthesize a series of 1-sterides-4-substituted piperazine compounds, wherein the 1-sterides-4-substituted piperazine compounds are expressed by general formulas (I) and (II). Pharmacological tests prove that the diosgenin piperazine compounds have the obvious inhibitory action on A375, A549 and HepG-2 cell strains, and are superior to diosgenin.

Description

technical field [0001] The invention relates to a novel diosgenin piperazine compound, a preparation method thereof, and an anti-tumor application of a pharmaceutical composition using the compound as an active ingredient. Background technique [0002] Diosgenin is a steroidal compound, which is abundant in nature and has various biological effects. At present, diosgenin is mainly used as a raw material for the synthesis of steroid hormones and as the main active ingredient in Chinese patent medicines for the treatment of cardiovascular diseases. [0003] In recent years, the antitumor activity of diosgenin has been paid more and more attention. Studies have shown that diosgenin can inhibit the growth and induce apoptosis of 1547, HEP-2, M4Beu, HT-29, K562, Hela, HEL cells, etc. . [0004] Research on the anti-tumor mechanism of diosgenin has also been paid attention to. The current research results show that diosgenin inhibits the growth of tumor cells by regulating apopt...

Claims

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Application Information

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IPC IPC(8): C07J71/00A61P35/00
Inventor 范举正张志荣傅微微曾春玲郑微吴亚克蒋红平
Owner SICHUAN UNIV
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