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Method for synthesizing marine polyhydroxyl sterol (25R)-5alpha -cholest-3 beta, 5alpha, 6beta, 26-tetrol

A technology of marine sterols and synthetic methods, which is applied in the field of synthesis of polyhydroxy marine sterols, can solve the problem of high extraction costs, and achieve the effects of scientific and reasonable synthetic routes, good selectivity, and high yield

Inactive Publication Date: 2009-10-21
SUN YAT SEN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(25R)-5α-cholesta-3β, 5α, 6β, 26-tetrol (its structural formula as I) is a natural polyhydroxy marine sterol present in Brasilia’s octagonal coral (Carijoa riisei). Has significant anticancer activity, its IC on tumor cell HCT-116 50 It is 2.0 μ g / mL (Gaya K.Liyanage and Francis J.Schmitz, J.Nat.Prod.1996,59,148-151), because the content of this sterol is very small, the extraction cost is very high, there is no bibliography to report this at present Compound Synthesis Method

Method used

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  • Method for synthesizing marine polyhydroxyl sterol (25R)-5alpha -cholest-3 beta, 5alpha, 6beta, 26-tetrol
  • Method for synthesizing marine polyhydroxyl sterol (25R)-5alpha -cholest-3 beta, 5alpha, 6beta, 26-tetrol

Examples

Experimental program
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Effect test

Embodiment 1

[0031] The synthesis method of the polyhydroxy marine sterol (25R)-5α-cholesta-3β, 5α, 6β, 26-tetrol provided in this example is as follows:

[0032] (1) Add compound II (15g, 37mmol) and absolute ethanol 1000ml in a 2L reaction flask, heat and reflux at 95°C to completely dissolve the saponin in ethanol, add 585g of zinc amalgam while it is hot, and use a constant pressure funnel to Concentrated HCl (400ml, 37.5%, w / w) was added to the reaction system, dripped in about 1h, continued to stir and heat to reflux for 4h, the reaction solution was concentrated under reduced pressure to remove ethanol, extracted 3 times with 150ml ethyl acetate respectively, organic The layer was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 10.8 g of white powder Compound III with a yield of 72%;

[0033] (2) Dissolve compound III (30g, 71.66mmol) in 300ml of anhydrous DMF, add i...

Embodiment 2

[0039] The synthesis method of the polyhydroxy marine sterol (25R)-5α-cholesta-3β, 5α, 6β, 26-tetrol provided in this example is as follows:

[0040] (1) Add compound II (15g, 37mmol) and absolute ethanol 1000ml in a 2L reaction flask, heat and reflux at 95°C to completely dissolve the saponin in ethanol, add 445g of zinc amalgam while it is hot, and use a constant pressure funnel to Add concentrated HCl (300ml, 37.5%, w / w) to the reaction system, follow the reaction by TLC, stop the reaction after the disappearance of the raw materials, filter, remove most of the ethanol under reduced pressure, extract 1 to 3 times with dichloromethane, and wash the organic layer with water to neutrality, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 13 g of white solid III;

[0041] Steps (2) to (6) in this embodiment are the same as steps (2) to (6) in Embodiment 1.

Embodiment 3

[0043] The synthesis method of the polyhydroxy marine sterol (25R)-5α-cholesta-3β, 5α, 6β, 26-tetrol provided in this example is as follows:

[0044] Steps (1) to (3) of this embodiment are identical to steps (1) to (3) in Example 1;

[0045] (4) Dissolve compound V (22.5g, 31.00mmol) in 440ml of anhydrous tetrahydrofuran, slowly add lithium aluminum hydride (3.51g, 91mmol) in batches and stir at room temperature for 16h. Sodium sulfate quenched the reaction, the reaction solution was white and turbid, washed with 5-10% (w / w) dilute hydrochloric acid, and the organic layer was washed with water until neutral, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 16.0 g of white powder VI, yield 83%;

[0046] (5) Dissolve compound VI (8g, 12.67mmol) in 480ml of dichloromethane, add 240ml of water and sodium carbonate (6g, 72.29mmol), slowly add m-chloroperbenzoic acid (8.67g, 50.24mmol) under stirring at room temperature ), finish the reaction...

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Abstract

The invention discloses a method for synthesizing marine polyhydroxyl sterol (25R)-5alpha-cholest-3beta, 5alpha, 6beta, 26-tetrol. Diosgenine is used as a raw material, and (25R)-5alpha-cholest-3beta, 5alpha, 6beta, and 26-tetrol are prepared by the steps of reduction ring-opening carried out by zinc amalgam, 3, 26-bit hydroxy protection carried out by tert-butyl dimethylchlorosilane, 16-bit hydroxyl esterification carried out by methylsufonyl chloride and sulfuryl, 16-bit methyl sulphonic acid ester reduction carried out by lithium aluminum hydride, 5-6-bit double linkage oxidation carried out by m-chloroperoxybenzoic acid, and ring opening and deprotection reaction under acid condition. The synthesizing method has the advantages of low-cost and easily obtained raw materials, moderate reaction condition, favorable selectivity and high yield, and the target compound has the potential antineoplastic and antiviral activity.

Description

technical field [0001] The invention relates to a method for synthesizing polyhydroxy marine sterols, in particular to a method for synthesizing (25R)-5α-cholesta-3β, 5α, 6β, 26-tetraol. Background technique [0002] Polyhydroxy marine sterols are steroidal substances widely distributed in marine organisms, and have significant activities in reducing blood lipids, anti-tumor, anti-oxidation, and neuroprotection. (25R)-5α-cholesta-3β, 5α, 6β, 26-tetrol (its structural formula as I) is a natural polyhydroxy marine sterol present in Brasilia’s octagonal coral (Carijoa riisei). Has significant anticancer activity, its IC on tumor cell HCT-116 50 It is 2.0 μ g / mL (Gaya K.Liyanage and Francis J.Schmitz, J.Nat.Prod.1996,59,148-151), because the content of this sterol is very small, the extraction cost is very high, there is no bibliography to report this at present Compound synthesis method. [0003] Contents of the invention [0004] The object of the present invention is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00A61P35/00A61P31/12
Inventor 张静夏颜光美邱鹏新黄奕俊黄顺芳
Owner SUN YAT SEN UNIV
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