Carboxyl substituted resveratrol analog compound and its preparation method

A technology of resveratrol and compound, applied in the directions of nitrile preparation, organic chemistry, drug combination, etc., can solve problems such as cell inability to complete transformation, reduction of cyclin protein expression, G1 phase arrest of epidermal cancer A431 cells, etc.

Inactive Publication Date: 2006-07-26
JIANGSU INST OF NUCLEAR MEDICINE
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Problems solved by technology

[0014] In 2001, Ahmad et al. [Ahmad N, Adhami VM, Afaq, et al. Resveratrol causes WAF-1 / p21-mediated G(I)-phase arrest of cell cycle and induction of apoptosis in huaman epidermoid careinoma A431 cells. Clin CancerRes, 2001, 7(5):1466] reported that resveratrol can induce the cyclin-dependent protein kinase (CDK) inhibitory protein p21 WAF-1 and can reduce the protein expression of cyclin D1, D2, E and CDK2, CDK4, CDK6, and then cause the G1 phase pause of human epidermal cancer A431 cells, so that the cells cannot complete the transition from G1 phase to S phase Transformation, which is considered irreversible and will eventually lead to apoptosis
But as a cancer drug, resveratrol is not strong enough

Method used

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  • Carboxyl substituted resveratrol analog compound and its preparation method
  • Carboxyl substituted resveratrol analog compound and its preparation method
  • Carboxyl substituted resveratrol analog compound and its preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0042] Embodiment 1: the synthesis of (E)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)acrylic acid

[0043] Synthesis of 3,5-dimethoxyphenylacetonitrile (4)

[0044] Solid sodium cyanide (14.3 g, 0.29 mol) was dissolved in distilled water (80 mL). Add absolute ethanol (80mL) into a 250mL three-necked flask, slowly add sodium cyanide solution under stirring, after the addition is complete, raise the temperature to 65°C, add 3,5-dimethoxybenzyl bromide (60g, 0.26mol), and complete the addition Reaction at 65°C for 1.5h. After the reaction, ethanol was evaporated under reduced pressure, cooled to room temperature, the precipitated solid was filtered, washed with water, recrystallized with methanol / water volume ratio 1 / 1, and dried to obtain the product, 44g of colorless needle crystals. Yield 96%, m.p.52-53°C.

[0045] Synthesis of 3,5-dimethoxyphenylacetic acid (3)

[0046] In a 150 ml three-neck flask, 17.7 g (0.1 mol) of 3,5-dimethoxyphenylacetonitrile (4) and 50 ml of metha...

Embodiment 2

[0051] Embodiment 2: the synthesis of (E)-2-(3,5-dihydroxyphenyl)-3-phenylacrylic acid

[0052] Synthesis of (E)-2-(3,5-dimethoxyphenyl)-3-phenylacrylic acid (2b)

[0053] Using similar reaction conditions as in Example 1, react 1.96 g of 3,5-dimethoxyphenylacetic acid (3) with 1.1 g of benzaldehyde, stir and heat up to 40° C. until the solid dissolves, add 0.7 g of potassium carbonate, and react for 2.5 hours 1.7 g of (E)-2-(3,5-dimethoxyphenyl)-3-phenylacrylic acid (2b) was obtained as a white powder solid, with a yield of 60% and a melting point of 203-205°C.

[0054] Synthesis of (E)-2-(3,5-dihydroxyphenyl)-3-phenylacrylic acid (1b)

[0055] Using the similar reaction conditions of Example 1, by 5.7g (2b) and 50mL, 2mol / L BBr 3 CH 2 Cl 2 The solution was reacted in 150 mL of dry dichloromethane, reacted at room temperature for 30 h, the reaction product was precipitated in ice water, filtered, and the solid was recrystallized with ethanol / water volume ratio 1 / 1 to obta...

Embodiment 3

[0056] Embodiment 3: Synthesis of (E)-2-(3,5-dihydroxyphenyl)-3-(4-nitrophenyl)acrylic acid

[0057] Synthesis of (E)-2-(3,5-dimethoxyphenyl)-3-(4-nitrophenyl)acrylic acid (2c)

[0058] Using similar reaction conditions as in Example 1, 1.96 grams of 3,5-dimethoxyphenylacetic acid (3) was reacted with 1.5 grams of p-nitrobenzaldehyde, stirred and heated to 40° C. until the solid was dissolved, and 0.7 grams of potassium carbonate was added. After reacting for 2.5 hours, 2.2 g of yellow needle-like crystal (E)-2-(3,5-dimethoxyphenyl)-3-(4-nitrophenyl)acrylic acid (2c) was obtained, with a yield of 67%. The melting point is 203-205°C.

[0059] Synthesis of (E)-2-(3,5-dihydroxyphenyl)-3-(4-nitrophenyl)acrylic acid (1c)

[0060] Using the similar reaction conditions of Example 1, by 6.6g (2c) and 50mL, 2mol / L BBr 3 CH 2 Cl 2 The solution was reacted in 150 mL of dry dichloromethane, reacted at room temperature for 24 hours, the reaction product was precipitated in ice water, ...

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Abstract

The resveratrol compound with carboxyl substituent has general formula as following, wherein, R acts for hydrogen, hydroxyl or nitryl. The opposite preparation method comprises: using Perkin reaction to the 3, 5-dimethoxylphenylacetic acid with opposite p-substituting R-benzaldehyde; removing the methoxy protection to obtain the product as the derivative of 1, 2-toluylene. This invention is similar to the resveratrol as 3, 4', 5-trihydroxy -trans-stilbene, and has wide application for antitumor and cardiovascular protection.

Description

technical field [0001] A class of resveratrol compounds with carboxyl substituents and a preparation method thereof relate to a class of 1,2-stilbene derivatives and belong to the fields of organic chemistry and medicinal chemistry. Background technique [0002] Resveratrol (resveratrol, chemical structure shown in structural formula 1), a derivative of 1,2-stilbene, its chemical name is 3,4',5-trihydroxy-trans-stilbene Ethylene (3,4',5-trihydroxystilbene), a colorless needle-like crystal, is easily soluble in organic solvents such as ether, chloroform, methanol, ethanol, acetone, and ethyl acetate. [0003] It produces fluorescence under the irradiation of 365nm ultraviolet light, and can react with ferric chloride-potassium ferricyanide for color development. [0004] [0005] Resveratrol [0006] Structural Formula 1 [0007] Resveratrol was first extracted from the plant veratrum gradiflurum by Takaoka in the early 1940s. It was ...

Claims

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Application Information

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IPC IPC(8): C07C59/52C07C51/08A61P35/00A61P9/00
Inventor 罗世能朱玉松谢敏浩刘娅灵邹霈何拥军吴军王洪勇俞惠新陈波奚月芬沈永嘉
Owner JIANGSU INST OF NUCLEAR MEDICINE
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