Trans-o-hydroxy stilbene derivative as well as preparation method and application thereof

A technology of o-hydroxystilbene and derivatives, which is applied in the field of preparation of trans-o-hydroxystilbene derivatives, can solve the problems of low yield, harsh reaction conditions, poor cis-trans stereoselectivity and the like, and achieves yield. The effect of high rate, short response time and convenient operation

Inactive Publication Date: 2014-12-10
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, they have disadvantages such as low yield, poor cis-trans stereoselectivity or harsh reaction conditions.

Method used

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  • Trans-o-hydroxy stilbene derivative as well as preparation method and application thereof
  • Trans-o-hydroxy stilbene derivative as well as preparation method and application thereof
  • Trans-o-hydroxy stilbene derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] In a 5mL single-port reaction flask, add 60mg (0.3mmol) 5-bromo-o-hydroxystyrene (1.0eq), 64mg3,5-dimethylphenylboronic acid, [Cp*RhCl 2 ] 2 3.7 mg (2%), CuOAc 120 mg (2.0 eq). Add 3 mL of methanol and stir at room temperature. After about 2 hours, TLC detected that the reaction was complete, and about 500 mg of silica gel was added, the solvent was evaporated, solidified, and the solid was loaded as a sample, and separated by column chromatography using petroleum ether and ethyl acetate as eluents. 52 mg of the product was obtained with a yield of 86%. The reaction formula is as follows:

[0046]

[0047] The physical properties and spectral data of the product are as follows: white solid; melting point: 90-92°C; 1 H NMR (CDCl 3 ,400MHz),δ:7.68(d,J=2.4Hz,1H),7.31-7.26(m,2H),7.20(s,2H),7.09(d,J=16.4Hz,1H),6.99(s, 1H), 6.75(d, J=8.4Hz, 1H), 5.08(s, 1H), 2.40(s, 6H); 13 C NMR (CDCl 3 ,100MHz), δ:152.1,138.3,137.0,131.8,131.1,130.0,129.7,127.2.124.7,121.1,117.7,...

Embodiment 2

[0049] In a 5mL single-port reaction flask, add 30mg (0.2mmol) 4-methoxy-o-hydroxystyrene (1.0eq), 89mg3,4,5-trimethylphenylboronic acid, [Cp*RhCl 2 ] 2 2.48 mg (2%), CuOAc 80 mg (2.0 eq). Add 2 mL of methanol and stir at room temperature. After about 2 hours, TLC detected that the reaction was complete, and about 500 mg of silica gel was added, the solvent was evaporated, solidified, and the solid was loaded as a sample, and separated by column chromatography using petroleum ether and ethyl acetate as eluents. 38 mg of the product was obtained with a yield of 60%. The reaction formula is as follows:

[0050]

[0051] The physical properties and spectrogram data of the product are as follows: Oil; 1 H NMR (CDCl 3 ,400MHz),δ:7.42(d,J=8.4Hz,1H),7.21(d,J=16.4Hz,1H),6.92(d,J=16.0Hz,1H),6.70(s,2H),6.51 (dd, J 1 =8.8Hz,J 2 =2.8Hz,1H),6.41(d,J=2.4Hz,1H),6.02(br,s,1H),3.88(s,6H),3.87(s,3H),3.76(s,3H); 13 C NMR (CDCl 3 ,100MHz), δ:160.3,154.5,153.4,137.4,134.1,128.0,127.7,...

Embodiment 3～23

[0054] The preparation methods of Examples 3-23 are the same as Example 1, except that the two raw materials are replaced with other similar structures, and the structures of the obtained products are listed in Table 1.

[0055] The product structure of embodiment 3~23

[0056]

[0057]

[0058]

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PUM

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Abstract

The invention discloses a trans-o-hydroxy stilbene derivative as well as a preparation method and application thereof. The preparation method comprises the following steps: in the presence of a rhodium catalyst and acetate, reacting an o-hydroxy styrene compound with arylboronic acid in a solvent, and after the reaction is completed, treating, thereby obtaining the trans-o-hydroxy stilbene derivative. The preparation method is mild in reaction conditions, procedures are simple and can be rapidly performed, and the yield is relatively high. The cell experiment shows that compared with resveratrol, a product prepared from the trans-o-hydroxy stilbene derivative is generally better in anti-tumor activity.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of a trans-o-hydroxyl stilbene derivative, and the anti-tumor cell growth ability of the compound is tested. Background technique [0002] Stilbene compounds are a class of substances with biological activity or medicinal value. In particular, stilbene substituted with hydroxyl group exhibited obvious anti-oxidative and anti-tumor properties. Trans-resveratrol (resveratrol) is a natural product with strong biological properties. It has obvious effects on various malignant tumor cells such as breast cancer, gastric cancer, colon cancer, prostate cancer, leukemia, ovarian cancer, and skin cancer. inhibition. The following are structural representatives of hydroxy-containing stilbenes with pharmaceutical activity: [0003] [0004] The methods commonly used in the past to synthesize stilbene compounds are mainly Wittig reaction and Mizoroki-H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/373C07C39/21C07C37/11C07C43/23C07C41/30C07C205/35C07C201/12C07C255/53C07C253/30A61P35/00
CPCC07C37/11C07C39/21C07C39/373C07C41/26C07C43/23C07C201/12C07C205/35C07C253/30C07C255/53
Inventor 崔孙良张岩侯廷军
Owner ZHEJIANG UNIV
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