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4-(4-hydroxy-3-methoxybenzene methylene) curcumin, preparation thereof and use in preparing anti-cancer medicament

A kind of technology of methoxybenzylidene and curcumin, applied in the field of synthesizing 4-curcumin

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

[0004] The literature closest to the compound 4-(4-hydroxyl-3-methoxybenzylidene) curcumin of the present invention has: Zambre, A.P etc. (Bioorg.Med.Chem.2006,14,7196-7204) synthesized 4-(2-hydroxybenzylidene), 4-(2,3-dihydroxybenzylidene), 4-(3,4-dihydroxybenzylidene) curcumin (compounds 2, 3 in sequence , 4), evaluated the activity of the above compounds to inhibit human leukemia cell KBM-5 (the cell is activated and proliferated by tumor necrosis factor-induced nuclear transcription factor), and the inhibitory activity to tumor cells Jurkat, H1299, and MM1, but the above compounds The activity is lower than that of curcumin

Method used

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  • 4-(4-hydroxy-3-methoxybenzene methylene) curcumin, preparation thereof and use in preparing anti-cancer medicament
  • 4-(4-hydroxy-3-methoxybenzene methylene) curcumin, preparation thereof and use in preparing anti-cancer medicament
  • 4-(4-hydroxy-3-methoxybenzene methylene) curcumin, preparation thereof and use in preparing anti-cancer medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1 Synthesis of 4-(4-hydroxy-3-methoxybenzylidene) curcumin.

[0017] Synthetic raw materials curcumin, 3-hydroxy-4-methoxybenzaldehyde (vanillin), and piperidine are from Sinopharm Chemical Reagent Co., Ltd., and all reagents are of analytical grade. Nuclear Magnetic Resonance Spectrometer (mercury-300, Varian Company of the United States) Ion Trap Mass Spectrometer (DECAX-30000, Thermo Finnigan Company of the United States); Micro-melting Point Apparatus (X-4, Shanghai Precision Instrument Factory).

[0018] Curcumin 2.2g (6mmol), methanol 50ml, add a catalytic amount of piperidine, vanillin 0.91g (6mmol), stir and react at room temperature for 48 hours, concentrate and remove the solvent, and the residue is separated and purified by silica gel column chromatography. The eluent is Ethyl acetate:petroleum ether=1:3 to obtain 0.9 g of reddish-brown powder (30% yield). mp96-98℃, molecular formula C 29 h 26 o 8 , 1 H NMR (300MHz, DMSO): δ (ppm) 3.72 (s, 3H, OC...

Embodiment 2

[0019] Example 2 4-(4-hydroxy-3-methoxybenzylidene) curcumin inhibits tumor cells K562, HL-60, B-16, SW480, HepG2, MGC80-3, SH-SY5Y, Bxpc-3 In vitro growth activity of:

[0020] 2.1. Cell lines

[0021] K562: Human chronic myelogenous leukemia blast cell line

[0022] HL-60: Human acute myeloid leukemia cell line

[0023] B16: mouse melanoma B16 cell line.

[0024] SW480: Human colon carcinoma cells

[0025] HepG2: human liver tumor cells

[0026] MGC80-3: human gastric cancer cells

[0027] SH-SY5Y: Human neuroblastoma cells

[0028] Bxpc-3: human pancreatic cancer cells

[0029] The above cells were all obtained from the Shanghai Cell Bank of the Chinese Academy of Sciences.

[0030] 2.2 Cell culture

[0031] See Table 1 for the formula of the cell culture medium, and the cells were kept at 37°C, 5% CO 2 Cultured in an incubator, and the cells in the logarithmic growth phase were used for proliferation and apoptosis experiments.

[0032] Table 1 Culture medium for...

Embodiment 3

[0042] Example 3 Inhibitory effect of intraperitoneal injection on B16 melanoma

[0043] 3.1 Materials BALB / C mice, aged 6-8wk, female, weighing 18g, were provided by the Shanghai Experimental Animal Center of the Chinese Academy of Sciences. Mouse melanoma B16 cell line. 4-(4-Hydroxy-3-methoxybenzylidene) curcumin is made into a solid dispersion, which is dissolved into a required concentration with physiological saline before use.

[0044] 3.2 Method

[0045] 3.2.1 Establishment of tumor-bearing mouse model B16 tumor cells were passed on for more than two generations, and the number of cells was adjusted to 10 7 / ml, 0.2mL / mouse, inoculate subcutaneously in the right forelimb of mice, inoculate 2 mice, wait for about two weeks, peel off the tumor, homogenate, and inoculate 30 mice again.

[0046] 3.2.2 Grouping were divided into 2 groups: the mice 24 hours after the inoculation of the tumor strain were randomly divided into 2 groups: Group I was the normal saline group (i.e...

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Abstract

The invention relates to a synthetic antineoplastic, in particular to the synthesis of 4-(4-hydroxy-3-methoxyl benzylidene) curcumin and an application thereof. The compound is prepared by the condensation of curcumin and Knovenagel. The compound, 4-(4-hydroxy-3-methoxyl benzylidene) curcumin can obviously inhibit various tumour cells, especially for K562, B16, HepG2, SW480 and SH-SY5Y cells. Compared with Cur, the compound has a better proliferation inhibition effect on K562, B16, HepG2, SW480 and SH-SY5Y cells obviously, and half inhibition concentration of the compound is about 1 / 9 of that of Cur. The compound can obviously inhibit size and weight of B16 tumor in vivo.

Description

technical field [0001] The invention relates to the synthesis of antitumor drugs, in particular to the synthesis of 4-(4-hydroxyl-3-methoxybenzylidene) curcumin and its application. Background technique [0002] Curcumin (curcumin, referred to as Cur) 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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IPC IPC(8): C07C49/255C07C45/74A61K31/122A61P35/00
Inventor 许建华刘洋李娜吴丽贤
Owner FUJIAN MEDICAL UNIV
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