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Icaritin analogue and its preparation method and application

The technology of icariin and its analogs is applied in the field of development and application of medicinal compounds, and can solve the problems of general anti-tumor effect of icariin and limited clinical application, etc.

Active Publication Date: 2021-04-27
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the general antitumor effect of icariin, its clinical application is limited.

Method used

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  • Icaritin analogue and its preparation method and application
  • Icaritin analogue and its preparation method and application
  • Icaritin analogue and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Synthesis of 8-((diethylamino)methyl)-2-(2,4-dimethoxyphenyl)-3,7-dihydroxy-4H-chroman-4-one (Ⅰ-1):

[0081]

[0082] To a solution of 2-(2,4-dimethoxyphenyl)-3,7-dihydroxy-4H-chroman-4-one (150 mg, 0.48 mmol) in EtOH (5 mL) was added formalin ( 37%, 1.3eq) and diethylamine (65 μL, 0.63mmol). The reaction mixture was stirred at 80°C for about 8 hours. The solution was then cooled to room temperature and the precipitated solid was collected by filtration, washed with methanol and recrystallized from ethanol to give a yellow solid in 80% yield. 1 H NMR (300 MHz, Chloroform- d ) δ 8.04 (d, J = 8.9 Hz, 1H), 7.56 (d, J = 8.5 Hz, 1H), 7.26 (s, 1H), 6.86 (d, J = 8.8 Hz,1H), 6.64 (dd, J = 8.4, 2.4 Hz, 1H), 6.60 (d, J = 2.3 Hz, 1H), 4.07 (s, 2H), 3.88 (s, 3H), 3.85 (s, 3H), 2.70 (q, J = 7.2 Hz, 4H), 1.16 (t, J = 7.2 Hz,6H).

Embodiment 2

[0084] Synthesis of 2-(2,4-dimethoxyphenyl)-3,7-dihydroxy-8-(pyrrolidin-1-ylmethyl)-4H-chroman-4-one (Ⅰ-2) :

[0085]

[0086] Referring to the synthetic method of compound (I-1), the yield was 70%. 1 H NMR (300 MHz, Chloroform- d ) δ 8.05 (d, J = 8.9 Hz, 1H), 7.56 (d, J = 8.4 Hz, 1H), 6.87 (d, J = 8.8 Hz, 1H),6.64 (dd, J = 8.5, 2.4 Hz, 1H), 6.60 (d, J = 2.3 Hz, 1H), 4.14 (s, 2H), 3.88(s, 3H), 3.86 (s, 3H), 2.73 (s, 4H), 1.90 (m, J = 3.5 Hz, 4H).

Embodiment 3

[0088] Synthesis of 2-(2,4-dimethoxyphenyl)-3,7-dihydroxy-8-(morpholinomethyl)-4H-chroman-4-one (Ⅰ-3):

[0089]

[0090] Referring to the synthetic method of compound (I-1), the yield was 85%. 1 H NMR (300 MHz, Chloroform- d ) δ 8.08 (d, J = 8.9 Hz, 1H), 7.57 (dd, J = 8.4, 0.4 Hz, 1H), 6.89 (d, J = 8.9Hz, 1H), 6.64 (dd, J = 8.4, 2.3 Hz, 1H), 6.61 (d, J = 2.3 Hz, 1H), 4.02 (s,2H), 3.89 (s, 3H), 3.87 (s, 3H), 3.80 (s, 4H), 2.65 (s, 4H).

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Abstract

The invention discloses an icariin analogue represented by formula I or II or a pharmaceutically acceptable salt thereof. The present invention discloses the above-mentioned icariin analogues for the first time, and proves that such compounds have therapeutic effects on breast cancer, multiple myeloma, acute promyelocytic leukemia and acute lymphoblastic leukemia, and can be applied to corresponding drug preparation.

Description

technical field [0001] The invention belongs to the development and application technology of medicinal compounds, in particular to an icariin analogue and its preparation method and application. Background technique [0002] Multiple myeloma (MM), characterized by the clonal expansion of malignant plasma cells, is a malignant disease. More than 100,000 cases of MM are diagnosed every year in the world, accounting for 1-2% of all malignant tumors and 10% of hematological tumors. Multiple myeloma (MM) is characterized by uncontrolled cell proliferation leading to the accumulation of mutated plasma cells (PCs) throughout the bone marrow. Too much abnormal PC production can lead to overcrowding of the bone marrow and prevent the full formation of other normal and healthy blood cells. Additionally, multiple myeloma is characterized by chromosomal heterogeneity and numerous mutations in a range of genes, both of which are difficult to target for the disease. MM is increasing i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30C07D407/12C07D405/12C07D405/06C07D498/04A61K31/352A61K31/4025A61K31/5377A61K31/4433A61K31/5365A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07D311/30C07D405/06C07D405/12C07D407/12C07D498/04Y02P20/55
Inventor 杨鹏辛贵忠后毅丁佳雨谢逸石姬明慧
Owner CHINA PHARM UNIV