Monohydroxy-2-acyl phenylacetate, and preparation and use thereof

A kind of technology of acyl phenylacetate and hydroxyphenylpropionic acid, applied in the field of monohydroxy-2-acyl phenylacetate and preparation thereof

Inactive Publication Date: 2009-04-15
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As analogues of polyhydroxy-2-acyl-phenylacetate, monohydroxy-2-acyl-phenylacetate compounds, and their preparation and activity, including the study of structure-activity relationship, have not been reported

Method used

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  • Monohydroxy-2-acyl phenylacetate, and preparation and use thereof
  • Monohydroxy-2-acyl phenylacetate, and preparation and use thereof
  • Monohydroxy-2-acyl phenylacetate, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 4-Hydroxy-2-octanoylphenylacetic acid ethyl ester (compound CsM4, R 1 =C 2 h 5 , R 2 =n-C 7 h 15 )

[0042] 1) 4-hydroxyphenylpropionic acid (compound 2, OH is at the C4 position of the benzene ring)

[0043] Add triethylamine formate (TEAF ) solution (9mL), heated to 95-100°C and stirred for 3h. Carefully add ice water, adjust to pH=1-2 with 6N hydrochloric acid, extract with ethyl acetate, combine extracts, wash with saturated sodium chloride solution, anhydrous MgSO 4 After drying and concentration under reduced pressure, the residue was purified by flash column chromatography to obtain 4-hydroxyphenylpropionic acid 2 with a yield of 85%.

[0044] 2) 6-hydroxy-2,3-dihydro-1-indanone (compound 3, OH is at C6 position)

[0045] Add 4-hydroxyphenylpropionic acid (6mmol), NaCl (60mmol), anhydrous AlCl in the reaction flask 3 (24mmol), the reaction mixture was stirred at 150°C for 2h, dissolved in 2N HCl solution, extracted with dichloromethane, combined organic...

Embodiment 2

[0057] 4-Hydroxy-2-decanoyl-phenylacetic acid ethyl ester (compound CsM5, R 1 =C 2 h 5 , R 2 =n-C 9 h 19 ) The preparation of CsM5 is from embodiment 1 intermediate product 6-benzyloxy-2,3-dihydro-1-indanone (compound 4, R=CH 2 C 6 h 5 )start.

[0058] 1) 6-benzyloxy-1-nonyl-3H-indene (compound 5, R=CH 2 C 6 h 5 , R 2 =n-C 9 h 19 )

[0059] According to the method described in Preparation Method 4) in Example 1, 6-benzyloxy-2,3-dihydro-1-indanone and Grignard reagent n-C 9 h 19 The reaction with MgCl gave 6-benzyloxy-1-nonyl-3H-indene 5 with a yield of 72%.

[0060] 2) 4-benzyloxy-2-decanoyl-phenylacetic acid (compound 6, R=CH 2 C 6 h 5 , R 2 =n-C 9 h 19 )

[0061] According to the method described in preparation method 5) in Example 1, 6-benzyloxy-1-nonyl-3H-indene was oxidized with acidic potassium dichromate to obtain 4-benzyloxy-2-decanoyl-benzene Acetic acid 6, yield 45%.

[0062] 3) ethyl 4-benzyloxy-2-decanoyl-phenylacetate (compound 7, R=CH 2 ...

Embodiment 3

[0067] 4-Hydroxy-2-butyryl-pentyl phenylacetate (compound CsM6, R 1 =n-C 5 h 11 , R 2 =C 3 h 7 )

[0068] The preparation of CsM6 is from embodiment 1 intermediate product 6-benzyloxy-2,3-dihydro-1-indanone (compound 4, R=CH 2 C 6 h 5 )start.

[0069] 1) 6-benzyloxy-1-propyl-3H-indene (compound 5, R=CH 2 C 6 h 5 , R 2 =C 3 h 7 )

[0070] According to the method described in Preparation Method 4) in Example 1, 6-benzyloxy-2,3-dihydro-1-indanone and Grignard reagent C 3 h 7 MgBr reaction followed by acidic hydrolysis afforded 6-benzyloxy-1-propyl-3H-indene 5 in 78% yield.

[0071] 2) 4-benzyloxy-2-butyryl-phenylacetic acid (compound 6, R=CH 2 C 6 h 5 , R 2 =C 3 h 7 )

[0072] According to the method described in preparation method 5) in Example 1, 6-benzyloxy-1-propyl-3H-indene was oxidized with acidic potassium dichromate to obtain 4-benzyloxy-2-butyryl-benzene Acetic acid 6, yield 50%.

[0073] 3) 4-benzyloxy-2-butyryl-pentyl-phenylacetate (compound 7, ...

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Abstract

The invention relates to single hydroxyl-2-acyl phenylacetic acid easter, a preparation method and the application thereof, which relates to a compound containing single hydroxyl-2-acyl phenylacetic acid easter structure, and provides single hydroxyl-2-acyl phenylacetic acid easter with novel structure, the preparation method and the application thereof. Single hydroxyl benzaldehyde 1 is used as raw material and is firstly converted into corresponding aryl benzene propanoic acid 2 by using Meldrum acid; under the effect of AlCl3, intramolecular acidylation happens to 2 to get compound 3; after passing through a protective hydroxyl, 3 is reacted with grignard reagent to get corresponding alkane coumarone 5 which is oxidized to get 2-acyl-phenylacetic acid compound 6; 6 is esterified by different sterols, and then a protecting group of 6 is removed to get the product single hydroxyl-2-acyl-phenylacetic acid easter CsM. The compound CsM can be used as potential anti cancer drug or other biological activity drugs.

Description

technical field [0001] The invention relates to a compound containing a monohydroxy-2-acylphenylacetate structure, in particular to a monohydroxy-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 et al. (Xu Qingyan et al., Journal of Xiamen University (Natural Science Edition), 2005, 44, 425-428) reported 10 structurally different 3,5-dihydroxy-2 isolated from fungal metabolites. -acyl-phenylacetate or its derivatives, and found that they have different antitumor activities. 3,5-dihydroxyl - Some biological activity test results of ethyl 2-o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/738C07C67/00A61K31/216A61P35/00
CPCY02P20/55
Inventor 张洪奎吴乔黄培强沈月毛
Owner XIAMEN UNIV
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