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1, 3-dioxolane derivative compound as well as preparation method and application thereof

A technology of dioxolane and compounds, applied in the field of medicine, can solve unseen problems

Inactive Publication Date: 2021-04-30
苑宝宇
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Prior art does not see the report of relevant structure

Method used

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  • 1, 3-dioxolane derivative compound as well as preparation method and application thereof
  • 1, 3-dioxolane derivative compound as well as preparation method and application thereof
  • 1, 3-dioxolane derivative compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1, the preparation of compound I

[0031] (1) Synthesis of 1-methoxy-1-phenylbut-3-en-2-ol (intermediate 1)

[0032]

[0033] To a solution of vinylmagnesium bromide (5.25 g, 40 mmol) in THF (30 mL) was added dropwise 2-methoxy-2-phenylacetaldehyde (5 g, 33.3 mmol) at 0°C. The mixture was stirred at 0 °C for 20 min, then washed with saturated NaHCO 3 (40 mL) solution to quench the reaction. The resulting solution was allowed to stand, and the layers were separated, the aqueous layer was extracted with ethyl acetate (3×20 mL), and the combined organic phases were dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure followed by column chromatography on silica gel (20% EtOAc in hexanes as eluent) to give 1-methoxy-1-phenylbut-3-en-2-ol as a yellow oil , 5.28g, yield 88.9%.

[0034] 1 H-NMR (400MHz, CDCl 3 )δ:2.79(d,1H),3.16(s,3H),4.85(m,2H),5.29(d,2H),6.07(m,1H),7.32-7.42(m,5H). 13 C-NMR (125MHz, CDCl 3)δ: 57.42, 78...

Embodiment 2

[0050] Embodiment 2, the preparation of compound 2

[0051] (1), 3-(4-methyl-1,3-dioxolan-2-yl)-5-(methoxy(phenyl)methyl)dihydrofuran-2(3H)-one ( Synthesis of Intermediate 4)

[0052]

[0053] 5-(Methoxy(phenyl)methyl)furan-2(5H)-one (4.08g, 20mmol) and benzophenone (0.36g, 2mmol) were dissolved in 4-[1,3]-dioxo The solution in pentane (1.94 g, 22 mmol) was degassed for 1 h under a stream of argon. The mixture was then irradiated for 12 hours using a 450 W ACE glass medium pressure mercury lamp from a distance of 15 cm. pass 1 The progress of the reaction was observed by H-NMR. The reaction flask was kept in a water-cooled environment as the reaction mixture was degassed and throughout the irradiation time. The temperature of the cooling water is kept at around 0°C. Removal of the solvent under reduced pressure followed by purification by silica gel column chromatography (35% EtOAc in hexanes as eluent) afforded 3-(4-methyl-1,3-dioxolan-2-yl as a beige solid )-5-(met...

Embodiment 3

[0057] Embodiment 3, the preparation of compound 3

[0058] (1), 3-(4,5-Dimethyl-1,3-dioxolan-2-yl)-5-(methoxy(phenyl)methyl)dihydrofuran-2(3H) - Synthesis of Ketone (Intermediate 4)

[0059]

[0060] 5-(Methoxy(phenyl)methyl)furan-2(5H)-one (4.08g, 20mmol) and benzophenone (0.36g, 2mmol) were dissolved in 4,5-dimethyl-[1 A solution in ,3]-dioxolane (2.25 g, 22 mmol) was degassed under argon flow for 1 h. The mixture was then irradiated for 12 hours using a 450 W ACE glass medium pressure mercury lamp from a distance of 15 cm. pass 1 The progress of the reaction was observed by H-NMR. The reaction flask was kept in a water-cooled environment as the reaction mixture was degassed and throughout the irradiation time. The temperature of the cooling water is kept at around 0°C. After the reaction was complete, the solvent was removed under reduced pressure followed by purification by silica gel column chromatography (35% EtOAc in hexane as eluent) to give 3-(4,5-dimethyl-1...

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Abstract

The invention belongs to the field of medicines, and relates to a 1, 3-dioxolane derivative compound as well as a preparation method and application thereof. The structural formula of the 1, 3-dioxolane derivative compound is as shown in formula I. Pharmacological studies show that the compound prepared by the invention can effectively inhibit the activity of tumor cells and promote the apoptosis of the tumor cells, and can be developed into a treatment method for Wnt / beta-catenin pathway cancers.

Description

technical field [0001] The invention belongs to the field of medicine, relates to a kind of 1,3-dioxolane derivative compound, and also relates to their preparation method. Background technique [0002] Malignant tumors are one of the most important diseases that seriously threaten human life. In recent years, with the continuous deepening of research and development of anticancer drugs, great progress has been made in cancer chemotherapy, especially the survival time of patients with hematological malignancies has been significantly prolonged. Due to the shortcomings of traditional anticancer drugs such as poor efficacy, strong side effects, and easy drug resistance, half of cancer patients are still unresponsive or resistant to treatment, which eventually leads to treatment failure, especially in the treatment of solid tumors. [0003] Like other intercellular signaling pathways, the Wnt signaling pathway also transmits signals from the cell surface to the nucleus by a se...

Claims

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Application Information

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IPC IPC(8): C07D407/04A61P35/00
CPCA61P35/00C07D407/04
Inventor 苑宝宇滕敏
Owner 苑宝宇
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