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Nitrogen mustard chromone derivative and application thereof

A technology of nitrogen mustards and chromone, applied in the field of natural medicine and medicinal chemistry, can solve the problems of high toxicity and side effects, lack of specificity of cell action, unsatisfactory therapeutic effect, etc., and achieve good anti-tumor cell proliferation effect

Active Publication Date: 2021-11-30
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of drug is widely used clinically, but its toxic and side effects are relatively large, and it lacks specificity for cell action. Moreover, with the occurrence of tumor drug resistance in recent years, the therapeutic effect is not ideal

Method used

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  • Nitrogen mustard chromone derivative and application thereof
  • Nitrogen mustard chromone derivative and application thereof
  • Nitrogen mustard chromone derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] (1) 500 mg of compound 1a (3.33 mmol) was dissolved in 10 mL of DMF, then 630 μL of phosphorus oxychloride (6.72 mmol) was added dropwise, and the reaction was carried out at room temperature for 12 h. TLC monitoring showed that the reaction was basically complete, 15 mL of water was added, and crystals were precipitated, suction filtration, and drying to obtain 402.4 mg of intermediate 2a. 50 mg of intermediate 2a (0.27 mmol) was dissolved in 10 mL of isopropanol, and 1 g of basic Al was added 2 O 3 (9.80 mmol), and then refluxed at 75°C for 5 h. TLC monitoring showed that the reaction was complete, filtered with suction, and the filtrate was concentrated to obtain the crude product, which was separated by silica gel column chromatography (DCM:MeOH) to obtain compound 3a (R=-CH). 3 ).

[0032] (2) 500 mg of melphalan 5 (1.64 mmol) was dissolved in 15 mL of formic acid, then 2 mL of acetic anhydride was added, and the reaction was carried out in an oil ba...

Embodiment 2

[0035]

[0036] The step of synthesizing 3a in step (1) of Example 1 was replaced with: 553 mg of compound 1b (3.33 mmol) was dissolved in 10 mL of DMF, then 630 μL of phosphorus oxychloride (6.72 mmol) was added dropwise, and the reaction was performed at room temperature for 12 h. TLC monitoring showed that the reaction was basically complete, 15 mL of water was added, and crystals were precipitated, suction filtration, and drying to obtain 410 mg of intermediate 2b. 55 mg of intermediate 2b (0.27 mmol) was dissolved in 10 mL of isopropanol, and 1 g of basic Al was added 2 O 3 (9.80 mmol), and then refluxed at 75°C for 5 h. TLC monitoring showed that the reaction was complete, filtered with suction, and the filtrate was concentrated to obtain the crude product, which was separated by silica gel column chromatography (DCM:MeOH) to obtain compound 3b (R=-OCH). 3 ).

[0037] For the remaining steps, referring to the synthetic method of Example 1, compound 7b was prepared ...

Embodiment 3

[0039]

[0040] The step of synthesizing 3a in step (1) of Example 1 was replaced with: 500 mg of compound 1a (3.33 mmol) was dissolved in 10 mL of DMF, then 630 μL of phosphorus oxychloride (6.72 mmol) was added dropwise, and the reaction was performed at room temperature for 12 h. TLC monitoring showed that the reaction was basically complete, 15 mL of water was added, and crystals were precipitated, suction filtration, and drying to obtain 402.4 mg of intermediate 2a. 50 mg of intermediate 2a (0.27 mmol) was dissolved in 10 mL of isopropanol, and 1 g of basic Al was added 2 O 3 (9.80 mmol), and then refluxed at 75°C for 5 h. TLC monitoring showed that the reaction was complete, filtered with suction, and the filtrate was concentrated to obtain a crude product, which was separated by silica gel column chromatography (DCM:MeOH) to obtain 15 mg of compound 3a. 500 mg of compound 3a (2.62 mmol) was dissolved in 10 mL of DCM, 750 μL of phosphorus tribromide (7.90 mmol) was ...

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Abstract

The invention discloses a nitrogen mustard chromone derivative and application thereof, belongs to the field of natural medicines and medicinal chemistry, and in particular relates to a preparation method of a series of nitrogen mustard chromone derivatives with anti-tumor activity and novel application of the nitrogen mustard chromone derivatives in the aspect of anti-tumor drugs. The nitrogen mustard chromone derivative and the pharmaceutically acceptable salt thereof are shown as a general formula I in the specification, wherein R, R1 and X are described in the claims and the specification.

Description

technical field [0001] The invention belongs to the field of natural medicine and medicinal chemistry, relates to a nitrogen mustard-like chromone derivative and its application, and in particular relates to a preparation method of a series of nitrogen mustard-like chromone derivatives with anti-tumor activity and its anti-tumor aspect the use of. Background technique [0002] Chromones are a class of oxygen-containing heterocyclic compounds with a benzo-γ-pyrone skeleton, which are widely distributed in nature and possess a variety of remarkable biological activities. Chromone and its derivatives show good anti-proliferative activity against breast cancer, liver cancer, lung cancer, leukemia and colon cancer, etc., and exert their effects through various mechanisms, and have great potential in cancer therapy. However, its further development and application are limited due to its poor bioavailability and insufficient activity strength. Therefore, the structure of chromone...

Claims

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Application Information

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IPC IPC(8): C07D311/22A61P35/00A61K31/352
CPCC07D311/22A61P35/00
Inventor 曹昊李达翃华会明孙迦南穆家辉焦润伟
Owner SHENYANG PHARMA UNIVERSITY
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