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

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

Inactive Publication Date: 2008-07-16
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The compound and its derivatives are expected to be further studied (XIONG Fu, Journal of Natnral Products, 1994, 57, (11), 1591-1594,) in aspects such as antitumor, antiviral, hypolipidemic, neuroprotective, etc., but the The content of the compound in marine organisms is very low, and there is no literature report on the synthesis method of the compound. In order to further study the pharmacological activity of the compound and its derivatives, the applicant conducted a synthesis study of the compound

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
Comparison scheme
Effect test

Embodiment 1

[0022]The method for synthesizing (25R)-5α-cholester-2β,3α,26-triol provided in Example 1 includes the following steps:

[0023] (1). Dissolve 50g (0.12mol) of Tignogenin II in 250ml of dry pyridine, add 45.8g (0.24mol) of p-toluenesulfonyl chloride, and stir for 24h at room temperature. The reaction solution was slowly poured into 1000 ml of 17% (w / w) HCl, a white precipitate was separated out, filtered with suction, the precipitate was washed with water to neutrality, and dried to obtain 68 g of white solid compound III with a yield of 99%.

[0024] (2). 30g (0.053mol) of compound III is dissolved in 450ml of dry DMF, and 45.6g (0.53mol) of LiBr and Li are added. 2 CO 3 39.2g (0.53mol), reflux for 1.5h. After cooling to room temperature, it was slowly poured into 10% (w / w) HCl, filtered with suction, the precipitate was washed with water to neutrality, and dried to obtain 23g of white solid powder compound IV. The yield was 87.8%.

[0025] (3). In a 2L three-necked round bottom ...

Embodiment 2

[0032] The synthesis method of (25R)-5α-cholester-2β,3α,26-triol provided in Example 2 includes the following steps:

[0033] (1). Same as Example 1.(1).

[0034] (2). 30g (0.053mol) of compound III is dissolved in 450ml of dry DMF, and 45.6g (0.53mol) of LiBr and Li are 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, the precipitate was washed with water to neutrality, and dried to obtain 23g of white solid powder compound IV, with a yield of 82%.

[0035] (3)~(8). Same as Example 1(3)~(8).

Embodiment 3

[0037] The synthesis method of (25R)-5α-cholester-2β,3α,26-triol provided in Example 3 includes the following steps:

[0038] (1)~(2). Same as Example 1.(1)~(2).

[0039] (3). In a 2L three-necked round bottom flask equipped with mechanical stirring, constant pressure dropping funnel and reflux condenser, add compound IV (15g, 37.7mmol) and 1100ml ethanol in turn, add 445g zinc amalgam, and drop under reflux 300ml of concentrated hydrochloric acid was added, and the reaction was followed by TLC, and the reaction was stopped when the raw materials disappeared. Filter, remove most of the ethanol under reduced pressure, extract 250 ml×3 times with dichloromethane, wash the organic layer with water until it is neutral, dry with anhydrous sodium sulfate, and concentrate to obtain 13 g of white solid. Purified by silica gel column chromatography (ethyl acetate: petroleum ether, V:V=3:7), 10.8 g of white solid compound V was obtained, with a yield of 65%.

[0040] (4)~(8). Same as Exampl...

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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 under their special environment, which contains a large number of substances with peculiar structure, strong physiological activity and special effects. Marine sterols are an important part of biofilms and the precursors of certain hormones. They have strong biological activity. (25R)-5α-cholesterol-2β, 3α, 26-triol is derived from marine organisms (Ophiarachna incrassara) A polyhydroxy marine steroid compound (M. Valeria D'Auria, J. Org. Chem, 1987, 52(18), 3947-3952) found in The 2β, 3α hydroxyl group has a unique 26-hydroxyl group on the 17-position side chain. [0003] [0004] The compound and its derivatives are expected to be further studied in such aspects as antitumor, antiviral, hypolipidemic, neuroprotection, etc. (XIONG Fu, Journal of Natnral Products, 1994, 57, (11), 1591-...

Claims

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Application Information

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IPC IPC(8): C07J9/00
Inventor 张静夏罗美凤
Owner SUN YAT SEN UNIV
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