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Bihydroxyl-2-acyl benzene acetic acid ester, producing method and uses thereof

A technology of acyl phenylacetate and methyl dihydroxybenzoate, which is applied in the field of bishydroxy-2-acyl phenylacetate and its preparation, and can solve the problems that have not yet been reported on the synthesis of CytosporoneB and its homologues, affecting research and application Progress, limited quantities, etc.

Inactive Publication Date: 2009-04-08
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, there is no report on the synthesis of Cytosporone B and its homologues so far
At present, Cytosporone B and its analogues are isolated from fungal metabolites, and their quantity is limited, which affects their research and application progress

Method used

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  • Bihydroxyl-2-acyl benzene acetic acid ester, producing method and uses thereof
  • Bihydroxyl-2-acyl benzene acetic acid ester, producing method and uses thereof
  • Bihydroxyl-2-acyl benzene acetic acid ester, producing method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] 3,5-dihydroxy-2-nonanoyl-phenylacetic acid ethyl ester (compound CsA2, R 1 =C 2 h 5 , R 2 =n-C 8 h 17 )

[0058] 1) Methyl 3,5-dihydroxybenzoate (compound 2)

[0059] 3,5-Dihydroxybenzoic acid (2.4mmol) was dissolved in 5mL of methanol, thionyl chloride (3.6mmol) was added, and the mixture was stirred at room temperature for 3h. Evaporate methanol and excess thionyl chloride, add water, extract with ethyl acetate, combine organic extracts, wash with sodium bicarbonate solution, anhydrous MgSO 4 After drying and concentration under reduced pressure, the residue was separated by column chromatography to obtain methyl 3,5-dihydroxybenzoate with a yield of 95%.

[0060] 2) Methyl 3,5-dibenzyloxybenzoate (compound 3, R=CH 2 C 6 h 5 )

[0061] Methyl 3,5-dihydroxybenzoate (20 mmol) was dissolved in 30 mL of acetone, benzyl bromide (43 mmol) and powdered anhydrous K 2 CO 3 (85 mmol), heated to reflux under stirring for 4.5 h, filtered, evaporated the solvent under...

Embodiment 2

[0077] 3,5-dihydroxy-2-octanoyl-phenylacetic acid ethyl ester (compound CsA1 (cytosporone B), R 1 =C 2 h 5 , R 2 =n-C 7 h 15) Preparation of CsA1 from the intermediate product 3,5-dibenzyloxyethyl phenylacetate 8 (R=CH 2 C 6 h 5 , R 1 =C 2 h 5 )start.

[0078] 1) 3,5-dibenzyloxy-2-octanoyl-phenylacetic acid ethyl ester (compound 9, R=CH 2 C 6 h 5 , R 1 =C 2 h 5 , R 2 =n-C 7 h 15 )

[0079] Ethyl 3,5-dibenzyloxyphenylacetate (1 mmol) was dissolved in trifluoroacetic anhydride (3.8 mL), n-octanoic acid (1.05 mmol) was added, and the mixture was stirred at room temperature for 48 h. Add 2 mL of sodium bicarbonate solution, extract with ether, combine the organic extracts, wash with saturated sodium chloride solution, anhydrous MgSO 4 Dry, concentrate under reduced pressure, and purify by column chromatography to obtain ethyl 3,5-dibenzyloxy-2-octanoyl-phenylacetate with a yield of 74%.

[0080] 2) 3,5-dihydroxy-2-octanoyl-phenylacetic acid ethyl ester (compo...

Embodiment 3

[0083] 3,5-Dihydroxy-2-propionyl-phenylacetic acid ethyl ester (compound CsA5, R 1 =C 2 h 5 , R 2 =C 2 h 5 ) Preparation of CsA5 From the intermediate product 3,5-dibenzyloxyethyl phenylacetate 8 (R=CH 2 C 6 h 5 , R 1 =C 2 h 5 )start.

[0084] 1) 3,5-dibenzyloxy-2-propionyl-phenylacetic acid ethyl ester (compound 9, R=CH 2 C 6 h 5 , R 1 =C 2 h 5 , R 2 =C 2 h 5 )

[0085] Ethyl 3,5-dibenzyloxyphenylacetate (0.8 mmol) was dissolved in trifluoroacetic anhydride (2.5 mL), propionic acid (0.96 mmol) was added, and the mixture was stirred at room temperature for 48 h. Add 1mL sodium bicarbonate solution, extract with ether, combine the organic extracts, wash with saturated sodium chloride solution, anhydrous MgSO 4 Dry, concentrate under reduced pressure, and purify by column chromatography to obtain ethyl 3,5-dibenzyloxy-2-propionyl-phenylacetate with a yield of 76%.

[0086] 2) 3,5-dihydroxy-2-propionyl-phenylacetic acid ethyl ester (compound CsA5, R 1 =C 2...

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Abstract

The invention provides a dihydric-2-acyl phenylacetate with a novel structure, a preparation method and application thereof, and relates to a compound containing the structure of the dihydric-2-acyl phenylacetate. The preparation method comprises the following steps: using dihydroxybenzoic acid 1 as a raw material, esterifying the dihydroxybenzoic acid 1, protecting hydroxyl group, reducing ester group to alcohol 4, and then treating the alcohol 4 by methylsulfonyl chloride and potassium cyanide in turn, obtaining cyanide 6, and then obtaining corresponding phenylacetate 8 by the action of alcohol and the cyanide 6 after the cyanide 6 is hydrolyzed into carboxylic acid; and obtaining an acidylation product (9) by the reaction of the phenylacetate 8 and R<2>CO2H under the action of trifluoroacetic anhydride or polyphosphoric acid, and finally removing the protected group to obtain the dihydric-2-acyl-phenylacetate CsA. Moreover, the dihydric-2-acyl-phenylacetate CsA can also be prepared by adopting an ester exchange method under acid catalysis. The related preparation method has the characteristics of easily obtained reagent, simple operation, high yield, and the like.

Description

technical field [0001] The invention relates to a compound containing a bishydroxy-2-acylphenylacetate structure, in particular to a bishydroxy-2-acylphenylacetate with antitumor activity and its preparation method and application. Background technique [0002] From the initial cytotoxicity to the current inhibitors of various biological targets, small organic molecules have always been one of the research hotspots of anti-tumor drugs. The research and development of compounds with novel structures and the search for new antitumor drugs are of great significance to the protection of human health. [0003] In 2005, Xu Qingyan from Xiamen University et al. (Xu Qingyan et al., Xiamen University Journal (Natural Science Edition), 2005, 44, 425-428) separated from the bark of the mangrove plant Tonghua tree in Fugong Town Mangrove Nature Reserve, Jiangkou, Jiulong, Fujian. Ten structurally different 3,5-dihydroxy-2-acyl-phenylacetate or its derivatives were isolated from the met...

Claims

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Application Information

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IPC IPC(8): C07C69/738C07C67/313A61K31/216A61P35/00
Inventor 张洪奎曾惠妮黄培强吴乔沈月毛
Owner XIAMEN UNIV
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