Method for preparing isoflavone metal complexes and anti-tumor medical application

A technology of metal complexes and hydroxy isoflavones, applied in the fields of natural medicinal chemistry, drug synthesis and pharmacology, can solve the problems of no isoflavone metal complex preparation methods and anti-tumor activity

Inactive Publication Date: 2010-10-13
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there is no research report on the preparation method and antitumor activity of isoflavone metal complexes

Method used

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  • Method for preparing isoflavone metal complexes and anti-tumor medical application
  • Method for preparing isoflavone metal complexes and anti-tumor medical application
  • Method for preparing isoflavone metal complexes and anti-tumor medical application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the preparation of 4'-methoxy-5,7-dihydroxyisoflavone-zinc complex (2)

[0020] Weigh 0.284g of 4'-methoxy-5,7-dihydroxyisoflavone ligand into a flask, dissolve it with an appropriate amount of absolute ethanol, add triethylamine dropwise to adjust the pH to 7-8, and stir at 40°C 1h, centrifuge at 2000r / min for 5min, and absorb the supernatant. Also weigh Zn(OAc) 2 2H 2 O 0.22g, dissolved in absolute ethanol, added dropwise to the ligand solution and stirred continuously, stirred at 60°C until a precipitate appeared, then continued to react for 6h, filtered out the precipitate, washed several times with ethanol to obtain 0.25g Pale yellow 4'-methoxy-5,7-dihydroxyisoflavone-zinc complex with a yield of about 40.3%. Its structural formula is as follows (see specification attached) figure 2 ):

[0021] figure 2 4'-Methoxy-5,7-dihydroxyisoflavone-zinc complex

[0022] IR(KBr): 3369(O-H), 1645(C=O), 1611, 1578, 1514, 1411(C=C), 1280(C-O-H), 1187(C-O-C...

Embodiment 2

[0023] Embodiment 2: Preparation of 4'-methoxy-5,7-dihydroxyisoflavone-manganese complex (3)

[0024] 4'-methoxyl group-5, the synthetic method step of 7-dihydroxyisoflavone-manganese complex is exactly the same as that of embodiment 1, just Zn(OAc) 2 2H 2 O was replaced by Mn(OAc) with the same mole number 2 2H 2 O, the brown solid was filtered out after the reaction, washed several times with ethanol, and the yield was about 42.1%. Its structural formula is as follows (see specification attached) image 3 ):

[0025] image 3 4'-Methoxy-5,7-dihydroxyisoflavone-manganese complex

[0026] IR(KBr): 3383(O-H), 1621(C=O), 1609, 1558, 1512, 1417(C=C), 1248(C-O-H), 1179(C-O-C), 732(Mn-O)cm -1 ; 1 HNMR (300MHz, DMSO-d 6 ): 3.71 (6H, s, 4', L4'-OCH 3 ), 5.32 (2H, s, 6, L6-H), 5.88 (2H, s, 8, L8-H), 6.49 (4H, d, 3′, 5′, L3′, L5′-H), 7.48 (4H, d, 2′, 6′, L2′, L6′-H), 8.34 (2H, s, 2, L2-H), 11.81 (2H, s, 7, L7-OH) ppm; EIMS m / z: 619.8 [M - , 100], 589.4, 336.1, 282.8; mol...

Embodiment 3

[0027] Embodiment 3: the preparation of 4'-methoxy-5,7-dihydroxyisoflavone-copper complex (4)

[0028] Weigh 0.284g of 4'-methoxy-5,7-dihydroxyisoflavone ligand into a flask, dissolve it with an appropriate amount of absolute ethanol, add triethylamine dropwise to adjust the pH to 7-8, and stir at 40°C 1h. Weigh another CuCl 2 2H 2O 0.168g was dissolved in absolute ethanol, and the ligand solution was added dropwise with continuous stirring. Immediately, solids were precipitated. Stirring was continued for 1 hour at 40°C, filtered, and the filter cake was discarded. The filtrate was placed at room temperature for several days to form a dark green precipitate. Suction filtration and washing several times with ethanol gave 0.5 g of powdery dark green solid with a yield of about 80.01%. Its structural formula is as follows (see specification attached) Figure 4 ):

[0029] Figure 4 4'-Methoxy-5,7-dihydroxyisoflavone-copper complex

[0030] IR(KBr): 3375(O-H), 1626(C=O), ...

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Abstract

The invention relates to a method for preparing isoflavone metal complexes shown as formulas I and II, and application of the isoflavone metal complexes. The definition of each group is shown in the description. The compounds and pharmaceutically acceptable salts thereof or hydrates thereof or solvate medicinal compositions thereof can be used for treating tumors and tumor angiogenesis or tumor metastasis medicaments. The structural formulas are shown in the attached figure 1 of the abstract.

Description

technical field [0001] The invention belongs to the technical fields of natural medicinal chemistry, drug synthesis and pharmacology, and specifically relates to an isoflavone metal complex, its preparation method and its use in the preparation of a broad-spectrum anti-tumor drug composition for inducing cell apoptosis , especially the application in pharmaceutical compositions for inducing apoptosis, anti-angiogenesis, and preventing malignant metastasis of tumor cells. Background technique [0002] The metal complexes of Pt(II) (also known as cisplatin) have anti-tumor activity and are one of the most widely used drugs in the clinical treatment of cancer, but its toxic side effects and cross-resistance limit it to a certain extent. application of these drugs. Compared with the commonly used platinum anticancer drugs, the advantages of non-platinum metal complex anticancer drugs are: (1) change the charge and oxidation state by coordinating with different metal ions; (2) c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36C07F3/06C07F1/08C07F13/00C07F15/00C07F15/06C07F15/04A61K31/352A61P35/00
Inventor 仇佩虹陈翔唐丽君孙玉娜林丽
Owner WENZHOU MEDICAL UNIV
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