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A kind of salamimol organosilicon compound and its antitumor application

A compound and application technology, applied in the field of medicinal chemistry and pharmacotherapeutics, can solve problems such as hair loss, limited drug application, and chemical drugs that cannot achieve therapeutic effects

Active Publication Date: 2022-03-04
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But at the same time, there are still the following deficiencies: first, the single-drug effective rate of these drugs in relapsed and refractory patients is only 25% to 50%; second, although the disease-free survival time is prolonged, most patients will eventually relapse, and Significant drug resistance appears; third, some serious side effects such as neuritis limit the application of drugs
However, antineoplastic drugs also have many adverse reactions, such as hair loss, vomiting, rapid development of drug resistance, etc., which lead to the inability of chemical drugs to achieve the expected therapeutic effect

Method used

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  • A kind of salamimol organosilicon compound and its antitumor application
  • A kind of salamimol organosilicon compound and its antitumor application
  • A kind of salamimol organosilicon compound and its antitumor application

Examples

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preparation example Construction

[0102] The present invention also provides the preparation method of the compound of the present invention.

[0103] A representative method for preparing compounds of formula I of the present invention includes:

[0104] Process I:

[0105]

[0106] OM is dissolved in an organic solvent, adding an organic base or an inorganic base and R2-X, stirring and reacting to obtain compound 1; then dissolving compound 1 in an organic solvent, adding an organic base or an inorganic base and R1-X, stirring and reacting, and the reaction solution undergoes conventional After post-treatment, Compound 2 is obtained, wherein R1 and R2 are as described in the first aspect of the present invention, and X is halogen.

[0107] In another preferred example, the organic solvent is selected from the group consisting of toluene, acetone, methylene chloride, 1,2-dichloroethane, tetrahydrofuran, acetonitrile, xylene, chlorobenzene, dioxane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide...

Embodiment 1

[0138]

[0139]1. Compound OM (11.45g, 50.0mmol) was dissolved in dichloromethane (200mL), stirred, added imidazole (8.16g, 120.0mmol), tert-butyldimethylsilyl chloride (9.06g, 60.0mmol), and monitored by TLC The reaction solution was diluted with water until the raw materials were reacted completely, the reaction solution was extracted with dichloromethane, the organic phase was separated, washed with water, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, and the residue was separated through a silica gel column (PE / EA, 5:1), the product OM-TBS (16.00 g) was obtained as a white solid with a yield of 93%.

[0140] OM-TBS 1 H NMR (400MHz, Chloroform-d): δ12.09(s,1H),7.87(s,1H),7.54–7.40(m,4H),7.05(dd,J=8.4,1.1Hz,1H),6.97 –6.86(m,3H),1.02(s,9H),0.23(s,6H). 13 C NMR (125MHz, Chloroform-d) δ166.30, 157.75, 138.98, 134.39, 129.66, 127.41, 124.99, 123.39, 123.30, 118.96, 81.65, 30.10, 22.65. ESI-MS 344.2...

Embodiment 2

[0144] Example 2 tested the activity inhibitory effect of the DCZ0858 compound prepared in Example 1 on tumor cells.

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Abstract

The invention relates to an organosilicon compound of salaminol and its antitumor application. Specifically, the present invention provides a compound, or an optical isomer thereof, or a racemate thereof, or a pharmaceutically acceptable salt thereof, or a prodrug thereof, characterized in that the compound has the following formula I structure . The compound of formula I in the present invention has an excellent effect of inhibiting tumor activity.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to an organosilicon compound of salaminol and its antitumor application. Background technique [0002] Malignant tumors, as one of the largest public health problems in the world, have greatly endangered human health and will become the number one killer of human beings in the new century. Malignant tumors are no longer just a serious disease in developed industrial countries, and developing countries are facing a greater burden of disease. Malignant tumors include solid tumors (such as lung cancer, colorectal cancer, liver cancer, gastric cancer, etc.) and blood tumors (such as myeloma, lymphoma, etc.). [0003] For example, multiple myeloma (multiple myeloma, MM) is a malignant disease of abnormal proliferation of clonal plasma cells. It is the second most common malignant tumor of the hematological system, accounting for about 10% of hematological mal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18A61K31/695A61P35/00A61P35/02
CPCC07F7/1804C07F7/1892A61P35/00A61P35/02
Inventor 李波施菊妹徐志建卜文宣张勇陆康朱维良
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI