Preparation method of combretastatin furan type analogues

A combretastatin and furan-type technology is applied in the field of preparation of combretastatin furan-type analogs, can solve problems such as unsatisfactory product yield, heavy metal residues, expensive raw materials, etc., and achieves easy industrialized production, mild reaction conditions, and easy operation. simple effect

Inactive Publication Date: 2016-05-11
LANZHOU UNIVERSITY
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Problems solved by technology

[0007] The raw materials of this type of method are expensive and difficult to prepare, and the Pd(PPh 3 ) 4 It ...

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  • Preparation method of combretastatin furan type analogues
  • Preparation method of combretastatin furan type analogues
  • Preparation method of combretastatin furan type analogues

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Embodiment Construction

[0027] The following examples can enable those skilled in the art to understand the present invention more comprehensively, but do not limit the present invention in any way. The raw materials used in the present invention are all known compounds, which can be purchased from the market or synthesized by methods known in the art.

[0028] according to figure 2 The reaction steps of the method for preparing combretastatin furan type analogue A shown:

[0029] Weigh 2.90g compound P 1 , 2.00g of 3,4,5-trimethoxybenzaldehyde and 100mL of THF were added to the reaction flask, and 2.20g of potassium tert-butoxide was added under stirring. After reacting for 10 minutes, TLC detected that after the reaction was complete, the solvent was evaporated, and the residue was separated and purified by silica gel column chromatography with a mobile phase of petroleum ether / ethyl acetate=50 / 2 to obtain compound C-1, 4.12 g, with a yield of 92%. Weigh 2.00 g of compound C-1 into a reaction f...

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Abstract

The invention provides a preparation method of combretastatin furan type analogues. The preparation method of the combretastatin furan type analogues (A and C) comprises the following steps of adding a solvent 1, a compound P1 and 3,4,5-triethoxy benzaldehyde into a reaction flask; adding alkali while stirring; reacting for 10 minutes at room temperature; adding diluted acid to regulate pH (Potential of Hydrogen) to be neutral; obtaining the combretastatin furan type analogue C through separation and purification; obtaining a compound A by reducing the C in a solvent 2 by using Raney Ni. The preparation method of combretastatin furan type analogues (B and D) comprises the following steps of adding the solvent 1, a compound P2 and 3-trimethylsilyl ether-4-methoxybenzaldehyde into the reaction flask; adding alkali while stirring; reacting for 10 minutes at the room temperature; adding the diluted acid to regulate pH (Potential of Hydrogen) to be neutral; obtaining the combretastatin furan type analogue D through separation and purification; obtaining a compound B by reducing the D in the solvent 2 by using the Raney Ni. The preparation method of the combretastatin furan type analogues, provided by the invention, has the advantages that the yield is high, the operation is simple, the reaction conditions are moderate, the used solvents are cheap and easy to get, industrial production is easy to realize, and the like.

Description

technical field [0001] The invention belongs to the field of medicines, in particular to a preparation method of combretastatin furan analogs Background technique [0002] Combretastatin is an anti-tumor drug targeting tumor blood vessels, which can quickly and selectively induce the collapse of existing blood vessels inside tumor tissues, block blood supply, and cause ischemic necrosis of tumor tissues. Sewan Theeramunkong et al. described in the literature (J. Med. Chem. 2011, 54, 4977-4986) the determination of the biological activity of combretastatin furan analogs A and B using neuroblastoma cell lines. The results showed that both A and B could inhibit cell survival and growth, exhibit similar cytotoxicity in HeLa cells, and induce severe G 2 / M block, eventually leading to cell death. In addition, the sulfur-containing groups connected to the furan ring on the precursor compounds C and D are beneficial to increase water solubility, introduce complex groups, and be l...

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Application Information

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IPC IPC(8): C07D307/64C07D307/42
CPCC07D307/42C07D307/64
Inventor 唐寿初刘腾马芳赖俊汕梁永平
Owner LANZHOU UNIVERSITY
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