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Formononetin derivative as well as preparation method and application thereof

A kind of technology of formononetin and derivatives, applied in the field of formononetin derivatives and preparation thereof

Pending Publication Date: 2021-12-28
广州鲁比生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that different formononetin derivatives may have inhibitory activity on different tumor cells

Method used

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  • Formononetin derivative as well as preparation method and application thereof
  • Formononetin derivative as well as preparation method and application thereof
  • Formononetin derivative as well as preparation method and application thereof

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preparation example Construction

[0050] The present invention also provides a preparation method for formononetin derivatives described in the above technical scheme, comprising the following steps:

[0051] mixing formononetin, ruthenium complex, potassium carbonate and a non-polar organic solvent, and performing a substitution reaction to obtain the formononetin derivative;

[0052] The formononetin has a structure shown in formula II, and the ruthenium complex has a structure shown in formula III:

[0053]

[0054] in, for

[0055]R is alkyl, substituted alkyl, alkoxy, hydroxy, carboxy, amino, alkenyl, alkynyl or phenyl.

[0056] In the present invention, unless otherwise specified, all preparation materials are commercially available products well known to those skilled in the art.

[0057] The invention mixes formononetin, ruthenium complex, potassium carbonate and non-polar organic solvent, and performs substitution reaction to obtain the formononetin derivative.

[0058] In the present invent...

Embodiment 1

[0079] The reaction process of formononetin derivatives:

[0080]

[0081] Compound RBL083 (195 mg, 0.2 mmol), anhydrous potassium carbonate (2 g, 14.7 mmol), DMF 15 mL. Add it into a 50mL round bottom flask, heat at 60°C for 30min, add 1mL of 1,4-dibromobutane dropwise, react at 60°C for 24h, and the reaction is complete. Suction filtration under reduced pressure, the filtrate was diluted with 100 mL of distilled water, extracted three times with 100 mL of methyl tert-butyl ether, and the aqueous phase was collected. Add 200 mg of sodium perchlorate to the aqueous phase to form an orange suspension, which is filtered under reduced pressure. After the filter cake was dried, it was purified by alumina column chromatography, eluted with toluene: acetonitrile (1:1), and the first eluate (orange band) was collected as the compound RBL083-BBr, with a yield of 60%;

[0082] Add formononetin (26.8mg, 0.1mmol), ruthenium complex (RBL083-BBr, 111.2mg, 0.1mmol) successively in the ...

Embodiment 2

[0085] The reaction process of formononetin derivatives:

[0086]

[0087] Compound RPL083 (205 mg, 0.2 mmol), anhydrous potassium carbonate (2 g, 14.7 mmol), DMF 15 mL. Add it into a 50mL round bottom flask, heat at 60°C for 30min, add 1mL of 1,4-dibromobutane dropwise, react at 60°C for 24h, and the reaction is complete. Suction filtration under reduced pressure, the filtrate was diluted with 100 mL of distilled water, extracted three times with 100 mL of methyl tert-butyl ether, and the aqueous phase was collected. Add 200 mg of sodium perchlorate to the aqueous phase to form an orange suspension, which is filtered under reduced pressure. After the filter cake was dried, it was purified by alumina column chromatography, eluted with toluene: acetonitrile (1:1), and the first eluate (orange band) was collected as the compound RPL083-BBr, with a yield of 65%;

[0088] Add formononetin (26.8mg, 0.1mmol), ruthenium complex (RPL083-BBr, 116mg, 0.1mmol) successively in the mi...

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Abstract

The invention relates to the technical field of medicinal chemistry, in particular to a formononetin derivative as well as a preparation method and application thereof. The invention provides a formononetin derivative. The formononetin derivative has a structure as shown in a formula I which is described in the specification. According to the invention, by utilizing the excellent reactivity, imaging capacity, binding capacity, oxidation-reduction capacity and good antitumor activity of polypyridine ruthenium complex, the polypyridine ruthenium complex is introduced to formononetin, and the formononetin is structurally modified, so that the antitumor activity is further improved.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a formononetin derivative and a preparation method and application thereof. Background technique [0002] Formononetin, one of the active isoflavones mainly isolated from plants such as red clover, Sophora flavescens and Astragalus membranaceus, has been shown to have anti-inflammatory, anti-cancer and antioxidant properties. In recent years, the anticancer activity of formononetin has been extensively studied, and it has been proven to have anticancer effects on a variety of cancer cells, including colon cancer, breast cancer, prostate cancer, nasopharyngeal cancer and lung cancer. Studies have shown that formononetin can regulate a variety of molecular signaling pathways, including cancer cell proliferation, cell cycle regulation, apoptosis, angiogenesis and metastasis, and has good anticancer potential against different cancer cells in vitro. In addition, formonon...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00A61K31/555
CPCC07F15/0053A61P35/00
Inventor 周淑媛
Owner 广州鲁比生物科技有限公司
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