Nitrogen mustard quercetin derivative, and preparation method and application thereof

A technology of quercetin and its derivatives, which is applied in the field of medicine and can solve problems such as the toxicity of metabolites

Active Publication Date: 2017-06-16
西安天一生物技术股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Nitrogen mustard quercetin derivative, and preparation method and application thereof
  • Nitrogen mustard quercetin derivative, and preparation method and application thereof
  • Nitrogen mustard quercetin derivative, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Preparation of Nitrogen Mustard Quercetin Derivatives (1)

[0020] N 2 Under protection, add 97.6mg (1.2mmol) of formaldehyde solution, 94.8mg (1.2mmol) of 2-chloroethylamine, 302mg (1.0mmol) of quercetin and 5 mL of ethanol into the closed reactor, add 4 drops of hydrochloric acid, Heat to 75-80°C for 3 hours, cool naturally, precipitate solid, filter with suction, and separate the crude product by chromatography (V (n-butanol): V (water): V (HOAc) = 4:1:1, wash with methanol Removed to obtain quercetin Mannich base yellow solid 129mg, yield 33.0%.

[0021] Take 393mg (1mmol) of the above-mentioned Mannich base, 431mg (2.2mmol) of 2-chloroethylphosphoryl dichloride, dissolve it with 5mL of dry DMF, and add 0.6mL of Et 3 The mixture of N and 4mL dry DMF was dripped over 30min, reacted at room temperature for 2h, then heated to 60°C, and the reaction was complete as monitored by TLC. Adjust the pH of the solution to 3-4 with 10% HCl solution, and then add 50mL of water...

Embodiment 2

[0023] Preparation of nitrogen mustard derivatives of quercetin (2)

[0024] Replace 431mg (2.2mmol) 2-chloroethylphosphoryl dichloride in Example 1 with 462mg (2.2mmol) (N-2-chloroethyl-N'-methyl) phosphoryl dichloride, other operations are the same as The same as in Example 1, the quercetin derivative (2) was obtained with a yield of 72.5%. MS (EIS)[M+H] + = 668.0.

Embodiment 3

[0026] Preparation of Nitrogen Mustard Quercetin Derivatives (3)

[0027] Replace 431mg (2.2mmol) of 2-chloroethylphosphoryl dichloride in Example 1 with 696mg (2.2mmol) L-(N-2-chloroethyl-N'-hydroxymethylbenzyl) phosphoryl dichloride Chlorine, other operations were the same as in Example 1 to obtain a quercetin derivative (3) with a yield of 71%. MS (EIS) [M+H] + = 880.1.

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Abstract

The invention relates to a nitrogen mustard quercetin derivative comprising a stereisomer or a tautomer, a preparation method of the nitrogen mustard quercetin derivative, a medicinal composition taking the derivative as an active component, and application of the medicine to cancer treatment. The preparation method of the derivative comprises the following steps: preparing Mannich alkali of quercetin from the quercetin, formaldehyde and chlorethamin, and performing reaction on the Mannich alkali and substituted phosphoramidic dichloride to prepare the nitrogen mustard quercetin derivative. The nitrogen mustard quercetin derivative has an anti-tumor effect.

Description

technical field [0001] The invention relates to nitrogen mustard quercetin derivatives and their application in pharmacy, belonging to the technical field of medicine. Background technique [0002] Quercetin is an important part of flavonoids, which has a wide range of pharmacological effects and biological activities, such as anti-oxidation and scavenging oxygen free radicals, lowering blood pressure, protecting myocardial ischemia, avoiding ischemia-reperfusion loss, enhancing immune function and Anticancer, antiviral and analgesic effects, etc. In recent years, the inhibitory effect of quercetin on the proliferation of human ovarian cancer, breast cancer, leukocytes, and gastrointestinal tumor cells has attracted much attention. Taking quercetin as the parent, modifying its structure and improving its drug activity is of great significance for the discovery of new drugs. [0003] Nitrogen mustards are a class of important anti-tumor drugs that directly act on DNA. They ...

Claims

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Application Information

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IPC IPC(8): C07F9/6584A61P35/00
CPCC07F9/65846
Inventor 史兰香张冀男刘斯婕张宝华郭瑞霞
Owner 西安天一生物技术股份有限公司
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