Synthesis of polyhydroxy ocean steroid (25R)-5 alpha-cholesteric-2 beta,3 alpha,26-triol

A synthetic method, -26-O- technology, applied in the direction of steroids, organic chemistry, etc., can solve the problem of low content and achieve a scientific and reasonable synthesis route

Inactive Publication Date: 2010-12-15
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] This compound and its derivatives are expected to be further studied in aspects such as anti-tumor, anti-virus, hypolipidemic, neuroprotective (XIONG Fu, Journal of Natnral Products, 1994 , 57, (11), 1591-1594,), but the content of this compound in marine organisms is very low, and there is no synthetic method of this compound reported in the literature. In order to further study the pharmacological activity of this compound and its derivatives, the applicant The synthesis of the compound was studied

Method used

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  • Synthesis of polyhydroxy ocean steroid (25R)-5 alpha-cholesteric-2 beta,3 alpha,26-triol
  • Synthesis of polyhydroxy ocean steroid (25R)-5 alpha-cholesteric-2 beta,3 alpha,26-triol

Examples

Experimental program
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Effect test

Embodiment 1

[0024] The synthetic method of (25R)-5α-cholesta-2β, 3α, 26-triol provided in Example 1 comprises the following steps:

[0025] (1). Dissolve 50 g (0.12 mol) of tegagenin II in 250 ml of dry pyridine, add 45.8 g (0.24 mol) of p-toluenesulfonyl chloride, and stir at room temperature for 24 hours. The reaction solution was slowly poured into 1000ml of 17% (w / w) HCl, a white precipitate was precipitated, filtered with suction, washed with water until neutral, and dried to obtain 68g of white solid compound III, with a yield of 99%.

[0026] (2). Compound III 30g (0.053mol) was dissolved in 450ml dry DMF, and LiBr 45.6g (0.53mol) and LiBr were added 2 CO 3 39.2g (0.53mol), refluxed for 1.5h. After cooling to room temperature, it was slowly poured into 10% (w / w) HCl, filtered with suction, washed with water until neutral, and dried to obtain 23g of compound IV as a white solid powder. Yield 87.8%.

[0027] (3). Add compound IV (15g, 37.7mmol) and 1100ml ethanol successively in ...

Embodiment 2

[0034] The synthetic method of (25R)-5α-cholesta-2β, 3α, 26-triol provided in Example 2 comprises the following steps:

[0035] (1). With embodiment 1. (1).

[0036] (2). Compound III 30g (0.053mol) was dissolved in 450ml dry DMF, and LiBr 45.6g (0.53mol) and LiBr were added 2 CO 3 39.2g (0.53mol), refluxed at 110°C for 4h. After cooling to room temperature, it was slowly poured into 10% (w / w) HCl, filtered with suction, washed with water until neutral, and dried to obtain 23g of compound IV as a white solid powder with a yield of 82%.

[0037] (3)~(8). Same as embodiment 1 (3)~(8).

Embodiment 3

[0039] The synthesis method of (25R)-5α-cholesta-2β, 3α, 26-triol provided in Example 3 comprises the following steps:

[0040] (1)~(2). With embodiment 1.(1)~(2).

[0041] (3). Add compound IV (15g, 37.7mmol) and 1100ml ethanol successively in a 2L three-neck round bottom flask equipped with mechanical stirring, constant pressure dropping funnel, and reflux condenser, add 445g of zinc amalgam, and drip under reflux Concentrated hydrochloric acid 300ml was added, the reaction was tracked by TLC, and the reaction was stopped after the disappearance of the raw material. Filter, remove most of the ethanol under reduced pressure, extract 250ml x 3 times with dichloromethane, wash the organic layer with water until neutral, dry over anhydrous sodium sulfate, and concentrate to obtain 13g of white solid. Purification by silica gel column chromatography (ethyl acetate:petroleum ether, V:V=3:7) gave 10.8 g of compound V as a white solid, with a yield of 65%.

[0042] (4)~(8). With e...

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Abstract

The invention discloses a synthetic method of a polyhydroxy marine steroid (25R)-5 Alpha- cholest-2 Beta and a 3 Alpha and 26-triol, which uses a low-cost Tigogenin as the raw material and obtains (25R)-5 Alpha-cholest-2-ene-16 Beta and 26-diol through the TsCl esterification, elimination reaction and the reduction of zinc powder / ethanol system, obtains (25R)-26-O- t butyl dimethysilyl-5 Alpha- cholest-2-ene through selectively protecting C-26- hydroxyl, C-16-hydroxyl ethlsulphonic acid esterification and lithium aluminum hydride reduction by t-butyl dimethylsilyl chloride, and at last gets the object compound (25R)-5 Alpha- cholest-2 Beta, 3 Alpha and 26-triol through ring-opening under the acid conditions after the epoxidation. The synthetic route of the invention is characterized in that: the synthetic raw material is of low-cost and easy to get; the synthetic route is scientific and reasonable, etc. The target compound has potential antitumor and antivirus activity.

Description

technical field [0001] The invention relates to a method for synthesizing polyhydroxy marine steroids. Background technique [0002] Marine organisms have developed their unique metabolic methods in their special environment, which contains a large number of substances with peculiar structures, strong physiological activities and special functions. Marine sterols are important components of biofilms and precursors of certain hormones, with strong biological activity. (25R)-5α-cholesta-2β, 3α, 26-triol is derived from marine organisms (Ophiarachna incrassara) A kind of polyhydroxy marine steroid compound (M.ValeriaD'Auria, J.Org.Chem, 1987,52 (18), 3947-3952) found in (M.ValeriaD'Auria, 3947-3952), its structural formula is as I, and the 2,3 positions of compound I have respectively 2β, 3α hydroxyl, unique 26-hydroxyl on side chain at position 17. [0003] [0004] The compound and its derivatives are expected to be further studied (XIONG Fu, Journal of Natnral Products,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00
Inventor 张静夏罗美凤
Owner SUN YAT SEN UNIV
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