4-(4-hydroxy3-methoxybenzene methyl) curcumin and use thereof in preparing anti-tumor medicament

A technology of methoxybenzyl and methoxybenzylidene, which is applied in the preparation of anti-tumor drugs and the field of synthesizing 4-curcumin, which can solve problems in the in vitro experiment stage

Active Publication Date: 2009-05-20
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The structural modification routes of curcumin at home and abroad mainly include: changing the type and position of substituents on the benzene ring, condensing β-diketone or forming a monoketone, changing the unsaturated conjugated link chain in the middle, reducing unsaturated double bonds, and active 4-position Methylene substitution, etc., the activity research is still in the stage of in vitro experiments

Method used

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  • 4-(4-hydroxy3-methoxybenzene methyl) curcumin and use thereof in preparing anti-tumor medicament
  • 4-(4-hydroxy3-methoxybenzene methyl) curcumin and use thereof in preparing anti-tumor medicament
  • 4-(4-hydroxy3-methoxybenzene methyl) curcumin and use thereof in preparing anti-tumor medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Example 1 Synthesis of 4-(4-hydroxy-3-methoxybenzyl)curcumin.

[0013] Synthetic raw materials 3-hydroxy-4-methoxybenzaldehyde (vanillin), 2,4-pentanedione, diboron trioxide, tri-n-butyl borate, n-butylamine, and piperidine are all from Sinopharm Chemical Reagent Co., Ltd. company. Catalytic hydrogenation device (Parr 1100, USA), NMR spectrometer (Unity 500, Varian Corporation, USA, 500MHz), ion trap mass spectrometer (DECAX-30000, Thermo Finnigan Corporation, USA); micro melting point apparatus (X-4, Shanghai Precision instrument factory).

[0014] Add 10g (0.1mol) of 2,4-pentanedione and 100ml of ethanol to a 250ml single-necked flask, add a catalytic amount of piperidine, and 15g (0.1mol) of vanillin, stir and react at room temperature for 48 hours, concentrate to remove the solvent, and recrystallize to obtain Light yellow powder intermediate A12.0g.

[0015] Add 100ml of acetone, 10g of intermediate A, 1g of 10% palladium carbon to a 250ml catalytic hydrogenatio...

Embodiment 2

[0017] Example 2 4-(4-hydroxy-3-methoxybenzyl) curcumin inhibits tumor cell K562, HL-60, B-16, SW480, HepG2, MGC80-3, the in vitro growth activity of SH-SY5Y:

[0018] 2.1. Cell lines

[0019] K562: Human chronic myelogenous leukemia blast cell line

[0020] HL-60: Human acute myeloid leukemia cell line

[0021] B16: mouse melanoma B16 cell line.

[0022] SW480: Human colon carcinoma cells

[0023] HepG2: human liver tumor cells

[0024] MGC80-3: human gastric cancer cells

[0025] SH-SY5Y: Human neuroblastoma cells

[0026] The above cells were all obtained from the Shanghai Cell Bank of the Chinese Academy of Sciences.

[0027] 2.2 Cell culture

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Abstract

The invention relates to a synthetic antineoplastic, in particular to the synthesis of 4-(4-hydroxy-3-methoxyl benzyl) curcumin and an application thereof for the preparation of the antineoplastic. After 2, 4-pentanedione and vanillin are condensed by Knovenagel, the compound is subjected to catalytic hydrogenation to obtain 3-(4-hydroxy-3-methoxyl benzyl)-2, 4-pentanedione and then the 3-(4-hydroxy-3-methoxyl benzyl)-2, 4-pentanedione and the vanillin are condensed by hydroxyaldehyde to obtain the 4-(4-hydroxy-3-methoxyl benzyl) curcumin. The compound is applied to the preparation of medicaments for the treatment of leukemia, skin cancer, gastric cancer, carcinoma of colon, hepatic carcinoma, breast cancer, prostatic carcinoma or other malignant tumors.

Description

technical field [0001] The invention relates to the synthesis of antitumor drugs, in particular to the synthesis of 4-(4-hydroxyl-3-methoxybenzyl) curcumin and its application in the preparation of antitumor drugs. Background technique [0002] Curcumin has thousands of years of edible and medicinal records in India, China, Japan, Korea and other places. At present, domestic and foreign studies have found that curcumin has various activities such as anti-tumor, anti-inflammation, anti-angiogenesis, anti-oxidation and neuroprotection. However, curcumin has poor water solubility, and its aqueous solution is unstable, especially under the condition of neutral to alkaline pH value. After oral administration, curcumin has fast metabolism in the body, low bioavailability, and low blood drug concentration. The main factor of clinical application. It is of great significance to synthesize curcumin derivatives through structural modification to enhance activity and water solubility...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/255C07C45/74A61K31/122A61P35/00
Inventor 许建华刘洋吴丽贤李娜
Owner FUJIAN MEDICAL UNIV
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