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Synthetic method of 24-methylene-cholesterol-3 beta, 5 alpha, 6 beta,19-tetraalcohol

A methylene and cholesteric technology, applied in the field of natural products, can solve the problems of difficult to meet demand, small quantity, difficult to collect in large quantities, etc., and achieves the effect of avoiding loss and high yield

Inactive Publication Date: 2003-10-15
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The content of 24-methylene-cholesta-3β, 5α, 6β, 19-tetrol in marine organisms is very small. Zeng Longmei et al. isolated 0.2g of this compound from 8.0kg of soft coral Nephtheatiexieral verseveldt, and this marine organism The quantity is not large, and it is not easy to collect in large quantities, so it is difficult to directly use marine organisms as raw materials to separate and extract this compound to meet the needs of today's society

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] (1). According to the method of "JianGuo Cui, LongMei Zeng, JingYu Su et al., Steroids, 2001, 66, 33-38", stigmasterol was synthesized through five steps to obtain 3β-acetoxy-cholesta-5- En-24-one, total yield 63%;

[0018] (2). 300 mg of 3β-acetoxy-cholest-5-en-24-one was dissolved in 3 mL of dioxane solution, and after cooling to 10°C in an ice-water bath, 0.15 mL of perchloric acid aqueous solution (concentration of 7%wt), in the dark, add 300mg N-bromoacetamide, add in eight times, and finish adding within 40 minutes. Remove the cooling bath, continue stirring at room temperature for 40 minutes, add 20 mL of dilute and cold sodium sulfite aqueous solution, extract four times with dichloromethane, combine the organic phases, wash with water, 5% sodium bicarbonate aqueous solution, and saturated saline until neutral, anhydrous Na2SO4 dried. Filtration, removal of solvent under reduced pressure gave a white solid, which was directly used in the next reaction, or sepa...

Embodiment 2

[0024] With reference to the method of embodiment 1, wherein:

[0025] The consumption of N-bromoacetamide in step (2) is 400mg;

[0026] The consumption of high lead acetate in step (3) is 900mg, and the reaction times is 7 hours;

[0027] The consumption of zinc powder is 500mg in the step (4), and the reaction times is 7 hours;

[0028] The consumption of hydrogen peroxide aqueous solution is 0.5mL in the step (5), and the consumption of methanol solution (containing 3%wt potassium hydroxide) is 15mL;

[0029] The consumption of methyltriphenylphosphine iodide in step (6) is 300mg;

[0030] Other conditions are identical with embodiment 1, obtain identical result.

Embodiment 3

[0032] With reference to the method of embodiment 1 and embodiment 2 respectively, wherein, step (6) replaces methyltriphenylphosphine iodide with an equivalent amount of methyltriphenylphosphine bromide, and other conditions are the same, and the result is the same.

[0033] Confirmation of the structure of the target product (24-methylene-cholesta-3β, 5α, 6β, 19-tetrol):

[0034] Melting point: 221-223°C, 224-226°C reported in literature

[0035] Specific rotation: [α] 20 D =+3.5° (c, 0.23, CH 3 OH), reported in literature as +2.6°(c, 0.347, CH 3 Oh)

[0036] Elemental analysis: C: 74.86, H: 10.86, C 28 h 48 o 4 Calculated values: C: 75.06, H: 10.71

[0037] FAB-MS: M + +1=449

[0038] IR: 3315, 1083, 2942, 2867, 1640, 1452, 1378, 1343, 1080, 1058, 1030, 879v / cm -1

[0039] 1 HNMR (DMSO-d 6 ):

[0040] 0.662(s, 3H, H-18), 0.906(d, J=6.5Hz, 3H, H-21), 0.977(d, J=3.5Hz, 3H, H-26), 0.991(d,

[0041] J=3.5Hz, 3H, H-27), 2.198(m, J=6.5Hz, 1...

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Abstract

The synthesis process of natural product 24-methene-cholest-3beta, 5alpha, 6beta, 19-tetrol (Nephalserol A) with antitumor and antiseptic activity includes the steps of: synthesis of 3beta-acetoxy-cholest-5-ene-24-one with easy-to-obtain stigmacholest; reaction of 3beta-acetoxy-cholest-5-ene-24-one with N-bromoacetamide in the catalysis of water solution of perchloric acid to produce 3beta-acetoxy-cholest-5alpha-bromo-6beta-hydroxy-24-one; photoannulation reaction to produce 3beta-acetoxy-cholest-5alpha-bromo-6, 19-epoxy-24-one; epoxy ring-opening reaction to produce 3beta-acetoxy-cholest-5-ene-19-hydroxy-24-one; oxidation of 5, 6-double bond with formic acid to obtain 3beta, 5alpha, 6beta, 19-tetrahydroxy-cholest-24-one; and final transforming the carbonyl group in 24-th place of branch chain into methane to obtain the destination product. The present invention has total yield of 9.3 %.

Description

technical field [0001] The present invention relates to the artificial synthesis of natural product 24-methylene-cholest-3β, 5α, 6β, 19-tetrol (24-methylene-cholest-3β, 5α, 6β, 19-tetrol; NephalsterolA) with significant physiological activity resolve resolution. Background technique [0002] 24-methylene-cholesta-3β, 5α, 6β, 19-tetrol (structure as shown in formula I, hereinafter referred to as the compound of formula I) was first obtained by Zeng Longmei et al from the soft corals Nephthea albida and N.tiexieral verseveldt in the South China Sea Separated and obtained (Wang Guiyangsheng, Li Fengying, Zeng Longmei, etc., Chemical Journal of Chinese Universities, 1992, 13, 623-627), the natural product is effective on human rectal cancer cells, human lung cancer cells, human oral cancer cells and mouse lymphoma cells. Possesses strong poisonous ability, ED 50 The values ​​were 0.81, 0.93, 0.39 and 0.34 μg / mL (ED 50 ≤4.0μg / mL is significantly inhibited, Chang-Yih Duh, Shang...

Claims

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Application Information

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IPC IPC(8): A61P31/04A61P35/00C07J9/00
Inventor 苏镜娱陆伟刚曾陇梅
Owner SUN YAT SEN UNIV
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