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Fat-soluble emodin derivative as well as preparation method application thereof

A derivative, emodin technology, applied in the field of emodin derivatives and its preparation, can solve the problem of unsatisfactory activity, etc., and achieve the effect of mild experimental conditions and simple synthesis method

Active Publication Date: 2018-01-05
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is currently known that emodin has the ability to inactivate HL60 (human promyelocytic leukemia cells), but because its activity is not ideal, emodin was chosen as the lead and chemically modified to improve its anti-tumor activity

Method used

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  • Fat-soluble emodin derivative as well as preparation method application thereof
  • Fat-soluble emodin derivative as well as preparation method application thereof
  • Fat-soluble emodin derivative as well as preparation method application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of fat-soluble emodin derivatives

[0025] (1) Preparation of 2-propylpentanoyl chloride (compound 1)

[0026]

[0027] 1. Reaction: Take a dry and clean 100 mL eggplant-shaped flask, dissolve 10 mmol 2-propylvaleric acid in 20 mL methylene chloride, and then add 12 mmol oxalyl chloride into the reaction system with a spatula. The mixed solution was stirred under ice bath conditions for 12 hours, and the reaction was stopped after TLC detected that there was no raw material in the system (developing system: dichloromethane:methanol=20:1, volume ratio);

[0028] 2. Purification: Spin dry directly with a rotary evaporator to obtain the crude product, and then purify to obtain 2-propylpentanoyl chloride (compound 1).

[0029] 1 3 δ 2.84 – 2.74 (m, 1H), 1.82 – 1.66 (m, 2H), 1.57 – 1.48 (m, 2H),1.43 – 1.32 (m, 4H), 0.93 (t, J = 7.2 Hz, 6H). 13 C NMR (101 MHz, CDCl 3 ) δ177.55, 56.93, 34.26, 20.35, 13.99. (In the actual production process, this step rea...

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Abstract

The invention discloses a fat-soluble emodin derivative and its preparation method and application. The specific structural formula of the compound is: . The compound can be obtained through a two-step reaction, the synthesis method is simple, the experimental conditions are mild, no harsh conditions such as high temperature and high pressure are required, and the yield is high. Compared with emodin (1,3,8-trihydroxy-6-methyl-9,10-anthraquinone), this compound has higher activity in inhibiting HL60 cell line (human promyelocytic leukemia cells), and is expected to be used in Medicines for treating leukemia.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to an emodin derivative and its preparation method and application. Background technique [0002] Leukemia is a type of clonal malignant disease derived from hematopoietic stem cells. Its typical feature is uncontrolled proliferation, resulting in the accumulation of a large number of leukemia cells, infiltrating the bone marrow and its adjacent tissues, and causing the normal hematopoietic dysfunction of the bone marrow. Therefore, how to control the infinite proliferation ability of tumor cells and induce their apoptosis is one of the key issues in tumor therapy. Bone marrow transplantation and traditional radiotherapy and chemotherapy cannot fully meet the needs of treatment. Radiotherapy and chemotherapy not only have limited curative effect, but also have serious adverse reactions. Bone marrow transplantation also involves graft-versus-host reaction (GVHD) and rec...

Claims

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Application Information

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IPC IPC(8): C07C46/00C07C50/34A61P35/02A61P35/00
Inventor 陈海军苏艺婷吴国林孙葛陈怡陈英玉胡建达
Owner FUZHOU UNIV
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