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Spin-labeling rotenone oxime ester, its preparation method and application

A technology of rotenone oxime and spin labeling, which is applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve problems such as unsatisfactory market development needs, limited resources, failure of chemotherapy, etc., and achieve excellent development and application prospects, and synthesis process Simple, high product purity effect

Inactive Publication Date: 2013-10-30
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present and for a long time to come, drugs will be one of the most important means of treating tumors. However, due to historical, economic and conceptual reasons, compared with developed countries, my country is relatively backward in the basic research and development of innovative anti-tumor drugs. , the source of drugs has long relied on imitation and imports, and the various anti-tumor drugs currently on the market have limited resources, single varieties, and high prices. They still cannot be popularized to the majority of tumor patients, and are far from meeting the development needs of the market.
At the same time, the drugs currently on the market are often accompanied by serious side effects and multidrug resistance during the treatment process, resulting in the failure of final chemotherapy.

Method used

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  • Spin-labeling rotenone oxime ester, its preparation method and application
  • Spin-labeling rotenone oxime ester, its preparation method and application
  • Spin-labeling rotenone oxime ester, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Synthesis of 12-N-[2′, 2′, 5′, 5′-tetramethyl-pyrroline nitroxide radical-3′-acyloxy]-rotenone oxime ester (compound 3a)

[0020] Synthesis of raw material rotenone oxime (2): 2mmol rotenone, 2.5mmol hydroxylamine and 2.5mmol sodium acetate were mixed, then 200mL ethanol was added, and refluxed for 12 hours. Crystallization appeared, filtered, washed with water, and dried to obtain the crude product. For the method used, refer to the method reported in the literature Yang Shiping, et al. Crystal Structure Communications, 2003, C59, 392-393.

[0021] Dissolve 1 mmol of rotenone oxime in 30 mL of dichloromethane, add 1.5 mmol of 3-carboxylic acid-2,2,5,5-tetramethylpyrroline nitroxide radical, and add 0.5 mmol of N, N -lutidine, and 1.5 mmol of dicyclohexylcarbodiimide was added, stirred at room temperature under argon protection for 5 hours, filtered to remove the white precipitate, and the solvent was removed under reduced pressure, the crude product was purified by co...

Embodiment 2

[0024] Synthesis of 12-N-[2′,2′,5′,5′-tetramethyl-tetrahydropyrroline nitroxide radical-3′-acyloxy]-rotenone oxime ester (compound 3b)

[0025] The experimental procedure is the same as in Example 1, only 3-carboxylic acid-2,2,5,5-tetrahydropyrroline nitroxide radical is used to replace 3-carboxylic acid-2,2,5,5-tetramethyl ylpyrroline nitroxide free radical. The detection data of the product obtained from the reaction are as follows: Yield: 82%; m.p.116-117°C; IR (KBr) cm -1 : 3436, 2973, 1763, 1621, 1513, 1458, 1355, 1217, 1080; ESR: An=14.76G, g 0 =2.0058; HRMS m / z calcd for C 32h 37 N 2 o 8 : 578.2623[M+H] + , found 578.2636[M+H] + .

Embodiment 3

[0027] Synthesis of 12-N-[2′, 2′, 6′, 6′-tetramethyl-tetrahydropyridine nitroxide radical-4′-acyloxy]-rotenone oxime ester (compound 3c)

[0028] The experimental procedure is the same as in Example 1, only 4-carboxylic acid-2,2,6,6-tetrahydropyridine nitroxide radical is used to replace 3-carboxylic acid-2,2,5,5-tetramethyl ylpyrroline nitroxide free radical. The detection data of the product obtained from the reaction are as follows:: Yield: 68%; m.p.124-126°C; IR (KBr) cm -1 : 3449, 2974, 1741, 1622, 1513, 1458, 1354, 1218, 1042; ESR: An = 15.28G, g 0 =2.0064; HRMS m / z calcd for C 33 h 37 N 2 o 8 : 590.2623[M+H] + , found 590.2638[M+H] + .

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Abstract

The invention discloses a spin-labeling rotenone oxime ester compound, its preparation method and application. The structural formula of the spin-labeling rotenone oxime ester compound is as show in the formula, wherein the substituent R can be 2,2,5,5-tetramethyl pyrroline nitronyl nitroxide radical, or 2,2,5,5-tetramethyl tetralin pyrroline nitronyl nitroxide radical, or -2,2,6,6-tetramethyl-tetralin pyridine nitronyl nitroxide radical or 2,2,6,6-tetramethyl-piperidine nitronyl nitroxide radical. The spin-labeling rotenone oxime ester compound provided by the invention can be applied in the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to a new class of spin-labeled rotenone oxime ester compounds, a preparation method of the compound and its use in the preparation of antitumor drugs. Background technique [0002] Tumor is one of the major malignant diseases with the highest mortality rate in the world, poses a major threat to human health and survival, and is one of the most important social problems faced by countries all over the world. There are more than 40 million cancer patients worldwide. At present, there are more than 1.6 million new cancer patients in my country every year, and at least 3 to 4 million cancer patients, and the annual death toll exceeds 1.3 million, and it is still on the rise. At present and for a long time to come, drugs will be one of the most important means of treating tumors. However, due to historical, economic and conceptual reasons, compared with developed countries, my country is relatively backward in the basic research and d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/14A61K31/4025A61K31/4433A61K31/453A61P35/00
Inventor 刘映前冯岗吕秀清杨柳张静
Owner LANZHOU UNIVERSITY
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