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Curcumin analogue, preparation method and application of curcumin analogue in medicine for resisting cancer cell proliferation

A curcumin analogue, cell proliferation technology, applied in chemical instruments and methods, anti-tumor drugs, drug combinations, etc., can solve low water solubility, rapid metabolism, low bioavailability, low anti-cancer effect, curcumin pharmacokinetics Problems such as poor kinetic properties, to achieve the effect of preventing cancer cell metastasis, inhibiting cell colony formation, inhibiting cell migration and invasion

Pending Publication Date: 2022-06-28
GUANGDONG TECHNION ISRAEL INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the poor pharmacokinetic properties of curcumin are still limited by low water solubility, rapid metabolism and low bioavailability, and curcumin, as a natural compound, has low anticancer effect

Method used

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  • Curcumin analogue, preparation method and application of curcumin analogue in medicine for resisting cancer cell proliferation
  • Curcumin analogue, preparation method and application of curcumin analogue in medicine for resisting cancer cell proliferation
  • Curcumin analogue, preparation method and application of curcumin analogue in medicine for resisting cancer cell proliferation

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Experimental program
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Effect test

Embodiment 1-7

[0058] A kind of curcumin analogue, its structural formula is shown in following general formula A, comprises the structure shown in any one of general formula A1-A7 in table 3, comprises following preparation steps:

[0059] (1) Preparation of 1,1'-ferrocene dicarbaldehyde: First, n-butyllithium solution (67ml, 1.6M, 0.10mol) was added dropwise to 200ml containing ferrocene (10g, 0.054mol) at room temperature and tetramethylethylenediamine (TMEDA) (14.7g, 0.25mol) in anhydrous hexane suspension; the mixed solution was stirred at room temperature for 18 hours, and an orange dilithiated ferrocene precipitate was precipitated. The liquid was cooled to 0°C, dimethylformamide (DMF) (7.85g, 0.11mol, 8.3ml) was added to the suspension, and it was stirred at room temperature for 2 hours for Bouveault aldehyde synthesis reaction; then precooled The reaction was quenched with hydrochloric acid (200ml, 5M), the mixture was extracted three times with ethyl acetate (100ml), the ethyl acet...

Embodiment 8-20

[0076] A curcumin analog, shown in its structural formula B, including the structure shown in any of the general formulas B1-B13 in Table 3, including the following preparation steps:

[0077] (1) Preparation of benzylidene acetone derivative: Benzaldehyde derivative (80.7 mmol), acetone (74 ml) and water (34 ml) were mixed well, followed by NaOH solution (30.3 mmol, 5.5 ml) and water (303 ml) Add to the solution to obtain a yellow mixture; the yellow mixture is stirred at room temperature for 20 hours, the organic layer is collected and concentrated in vacuo to give the corresponding benzylidene acetone derivative.

[0078] (2) Preparation of curcumin analog compound: 1,1'-Ferrocene dicarbaldehyde (0.5 mmol) and the above benzylidene acetone derivative (1 mmol) were dissolved in methanol (30 ml), and NaOH solution (1.5 mmol) was added. M, 5 ml), stirred at room temperature for 24 hours; the mixture was concentrated to dryness under vacuum, and the product was purified by colu...

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Abstract

The invention belongs to the field of chemical drugs, and particularly discloses a curcumin analogue, a preparation method and application of the curcumin analogue in drugs for resisting cancer cell proliferation. The curcumin analogue comprises a structure as shown in a general formula A or a general formula B. The curcumin analogue with the structure as shown in the general formula A consists of 1, 2, 4-trimethyl-1, 3- the curcumin analogue with the structure as shown in the general formula A is prepared from a benzalacetone derivative and 1, 1 '-ferrocene dicarboxaldehyde through a Claisen-Schmidt condensation reaction, and the curcumin analogue with the structure as shown in the general formula B is prepared from a benzalacetone derivative and 1, 1'-ferrocene dicarboxaldehyde through a Claisen-Schmidt condensation reaction. According to the application, a ferrocene group is introduced into a natural active compound molecule, so that the biological activity of a parent compound can be improved to different extents, and therefore, the curcumin analogue has an anti-cancer effect higher than that of curcumin, and meanwhile, the curcumin analogue has special selective toxicity, low toxicity to normal cells and high toxicity to cancer cells; the compound has excellent anti-cancer cell proliferation activity and toxicity selectivity.

Description

technical field [0001] The invention relates to the field of chemical medicines, in particular to a curcumin analogue and a preparation method and its application in anti-cancer cell proliferation medicines. Background technique [0002] Breast cancer is one of the most common malignancies in women and is a heterogeneous disease at both the biological and clinical levels. However, most deaths from breast cancer are not due to the primary tumor itself, but to death due to metastasis to other organs of the body, such as the lungs and brain. Studies have shown that women with breast cancer without metastases have a 98% survival rate, while women with breast cancer metastases have a survival rate of only 27%. Therefore, using the metabolic processes of breast cancer cells as drug targets, such as cell migration, cell invasion, cell proliferation and cell cycle arrest, may provide a new idea for the treatment of breast cancer. [0003] Curcumin is a phenolic compound mainly iso...

Claims

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Application Information

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IPC IPC(8): C07F17/02A61P35/00
CPCC07F17/02A61P35/00
Inventor 杨琼琼高海德
Owner GUANGDONG TECHNION ISRAEL INST OF TECH
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