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Chromone nitrogen mustard derivative and anti-tumor application

A technology for chromogen mustard and derivatives, which is applied in the fields of natural medicine and medicinal chemistry, can solve problems such as drug resistance with side effects, and achieve the effect of good anti-tumor cell proliferation effect.

Active Publication Date: 2021-12-14
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because of its non-specificity to cancer cells, large doses are often required to kill cancer cells.
However, the use of large doses of nitrogen mustard will cause serious side effects and drug resistance, limiting its further clinical application

Method used

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  • Chromone nitrogen mustard derivative and anti-tumor application
  • Chromone nitrogen mustard derivative and anti-tumor application
  • Chromone nitrogen mustard derivative and anti-tumor application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

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

[0032] (2) Add 5 mL of ethylene oxide (0.10 mol) to a suspension of 1.53 g of ethyl 4-aminobenzoate 5 (9.26 mmol) dissolved in 12 mL of 65% aqueous acetic acid, and stir at room temperature for 24 h. After the reaction was complete, it was...

Embodiment 2

[0035]

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

[0037] The rest of the steps were prepared according to the synthetic method of Example 1 to obtain compound 8b as a yellow oil with a yield of 43.8%. 1 HNMR (CDCl...

Embodiment 3

[0039]

[0040] The step of synthesizing 3a in step (1) of Example 1 was replaced by: dissolving 500 mg of compound 1a (3.33 mmol) in 10 mL of DMF, then adding 630 μL of phosphorus oxychloride (6.72 mmol) dropwise, and reacting at room temperature for 12 h. TLC monitoring showed that the reaction was almost complete. When 15mL of water was added, crystals were precipitated. After suction filtration and drying, 402.4mg of intermediate 2a was obtained. Dissolve 50 mg of intermediate 2a (0.27 mmol) in 10 mL of isopropanol and add 1 g of basic Al 2 o 3 (9.80mmol), and then reflux at 75°C for 5h. TLC monitoring showed that the reaction was complete. Suction filtration was performed, 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. 500mg of compound 3a (2.62mmol) was dissolved in 10mL of DCM, 750μL of phosphorus tribromide (7.90mmol) was added dropwise under ice coolin...

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Abstract

The invention discloses a chromone nitrogen mustard derivative and anti-tumor application, and belongs to the field of natural medicines and medicinal chemistry. The invention particularly relates to a preparation method of a series of chromone nitrogen mustard derivatives with anti-tumor activity and novel application of the chromone nitrogen mustard derivatives in anti-tumor drugs. The chromone nitrogen mustard derivative and the pharmaceutically acceptable salt thereof disclosed by the invention are shown in a general formula I in the specification. R 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 class of chromone mustard derivatives and anti-tumor applications, in particular to a series of preparation methods of chromone mustard derivatives with anti-tumor activity and their anti-tumor effects the use of. Background technique [0002] The chromone skeleton is an important part of a large number of bioactive molecules, and also the core part of many natural products, lead compounds and clinical drugs. Chromone can be synthesized to obtain derivatives with various structures, which can be used as lead compounds for structural modification to synthesize a variety of derivatives with different pharmacological activities. At present, chromone and its derivatives have become one of the most important synthetic compounds with anticancer activity, and researches on the synthesis and structural modification of chromone are active at home and abroad. [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22A61K31/352A61P35/00
CPCC07D311/22A61P35/00Y02P20/55
Inventor 曹昊李达翃华会明孙迦南穆家辉高祥
Owner SHENYANG PHARMA UNIVERSITY
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