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A class of thiaevodipine compounds and their application in antitumor drugs

An anti-tumor drug, a technology of hybrid evodiam, applied in the field of medicine, can solve the problems of low anti-tumor activity, poor selectivity of evodial derivatives, normal cytotoxicity that cannot be ignored, etc., and achieves the effect of good activity and low toxicity

Active Publication Date: 2019-08-02
INST OF BOTANY JIANGSU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, many evodiamine derivatives have been synthesized. Studies by Zhang Wannian and Sheng Chunquan of the Second Military Medical University in China have found that evodiamine derivatives have significant inhibitory activity on topoisomerase Ⅰ and have a broad anti-tumor spectrum. However, evodiamine derivatives In the case of poor selectivity, the toxicity to normal cells cannot be ignored
At present, there are few researches on the antitumor activity of evodiamine and its derivatives, and the derivatives with high antitumor activity and low toxicity are still the focus of research. On the basis of previous studies, the present invention has obtained a class of Thia-evodiamine compound with tumor activity and low toxicity

Method used

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  • A class of thiaevodipine compounds and their application in antitumor drugs
  • A class of thiaevodipine compounds and their application in antitumor drugs
  • A class of thiaevodipine compounds and their application in antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of compound 2 (thioevodiamine)

[0026] In a three-necked flask equipped with a thermometer and a condenser tube, add evodiamine (0.50 g, 3.50 mmol), Lawson’s reagent (2.12 g, 5.25 mmol), toluene (100 mL), and stir the reaction at 110 °C for 6 h. Thin-layer chromatography (TLC), the developer is petroleum ether (PE): ethyl acetate (EtOAc) = 5:1) to monitor the reaction. After the reaction, the solvent was removed by rotary evaporation, and the product was separated and purified by silica gel column chromatography (elution condition PE:EtOAc=2:1). The product is yellow crystals, 0.29 g, yield: 54.5%, product purity: 99.9%; m.p. 216-218 ℃, TLC developer: PE : EtOAc = 5:1, product Rf value 0.52, separated and purified by silica gel column chromatography , Elution condition PE: EtOAc= 2:1; FT-IR: 3445( ν C-H ,Ar-H), 3051 ( υ C-H , CH 3 ), 2920( υ C-H , CH 2 ), 2898 ( υ C-H , CH), 1617 ( υ C=O , N-C=O),1595( υ C=C ), 1471( δ C-H ,...

Embodiment 2

[0027] Embodiment 2: the synthesis of compound Ia

[0028] In a three-necked flask equipped with a thermometer and a condenser tube, add thioevodiamine (0.20 g, 0.66 mmol), NaH (20.59 mg, 0.86 mmol), DMF (10 mL, 4Å molecular sieve to remove water), and stir at room temperature for 20 min, slowly added halogenated hydrocarbon (0.99 mmol). The reaction was stirred at 50 °C and monitored by TLC. Post-treatment after the reaction: add water (10 mL) to quench the reaction, extract with ethyl acetate (20 mL) three times, combine the organic phases, wash twice with saturated brine, anhydrous Na 2 SO 4 Dry for 2 h, filter with suction, remove the solvent by rotary evaporation, and separate and purify by silica gel column chromatography to obtain the product. Yellow crystal, 0.20g, yield: 87.6%, product purity: 99.9%; m.p. 163-165 ℃; TLC developer is PE: EtOAc = 1:1, product Rf value is 0.24, separated and purified by silica gel column chromatography, washed Deconditioning PE: EtOA...

Embodiment 3

[0029] Embodiment 3: the synthesis of compound Ib

[0030] In a three-necked flask equipped with a thermometer and a condenser tube, add thioevodiamine (0.20 g, 0.66 mmol), NaH (20.59 mg, 0.86 mmol), DMF (10 mL, 4Å molecular sieve to remove water), and stir at room temperature for 20 min, slowly added halogenated hydrocarbon (0.99 mmol). The reaction was stirred at 50 °C and monitored by TLC. Post-treatment after the reaction: add water (10 mL) to quench the reaction, extract with ethyl acetate (20 mL) three times, combine the organic phases, wash twice with saturated brine, anhydrous Na 2 SO 4 Dry for 2 h, filter with suction, remove the solvent by rotary evaporation, and separate and purify by silica gel column chromatography to obtain the product. Yellow crystal, 0.18g, yield: 78.8%, product purity: 98.5%; m.p. 176-178 ℃; TLC developer is PE: EtOAc=5:1, product Rf value is 0.45, silica gel column chromatography, elution conditions : PE:EtOAc = 20:1; FT-IR: 3138 ( υ C...

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Abstract

The invention discloses a thia rutaecarpin compound and application thereof to antitumor drugs. The thia rutaecarpin compound aims at performing structure modification by taking rutaecarpin as a raw material, so as to obtain a thia rutaecarpin derivative with high antitumor activity and low toxicity, and the compound has a good effect particularly on human breast cancer, colon cancer and ovarian cancer, but has low toxicity for normal human cells, such as human lung fibroblasts. The invention further provides the compound and the application of salt of the compound to the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a thia-evodiamine compound and a medicinal salt thereof, a preparation method thereof and an application in preparation of antitumor drugs. Background technique [0002] Tumor is a new organism formed by local tissue cell proliferation under the action of tumorigenic factors, because this new organism is mostly in the form of space-occupying blocky protrusions, also known as neoplasm. Tumors can be divided into two categories, namely benign tumors and malignant tumors. Those that cause greater damage to the body are called malignant tumors, and cancer is the general term for malignant tumors. Malignant tumor is a common and frequently-occurring disease that poses a serious threat to human health and life. It occupies the first place in the cause of death in cities and the second place in rural areas. Due to the influence of various aspects such as the surrounding environment, l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14A61P35/00
CPCC07D471/14
Inventor 刘飞王奇志单宇冯煦郭现翠印敏管福琴陈雨赵兴增徐曙王碧王鸣赵友谊
Owner INST OF BOTANY JIANGSU PROVINCE & CHINESE ACADEMY OF SCI
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