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Disulfide compound as well as preparation method and application thereof

A disulfide and compound technology, applied in the field of new disulfide compounds and their synthesis, can solve the problems of human and environmental hazards, alkyl thiol odor, etc., and achieve low production cost, simple operation, and good anti-tumor activity Effect

Inactive Publication Date: 2012-08-22
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the past, the synthesis of disulfide compounds was mainly obtained by the reaction between two mercaptans. The alkyl mercaptans used had a foul smell and were harmful to the human body and the environment.

Method used

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  • Disulfide compound as well as preparation method and application thereof
  • Disulfide compound as well as preparation method and application thereof
  • Disulfide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation of embodiment 1, sodium ethyl thiosulfate:

[0036] Mix 10mmol ethyl iodide, 2.48g sodium thiosulfate pentahydrate with 25mL 75% ethanol-water solution, heat and reflux for 2 hours, after detection the sodium thiosulfate completely disappears, lower the temperature, and use it directly for the next reaction.

Embodiment 2

[0037] Embodiment 2, the preparation of ethyl-(2-benzoxazole) disulfide (1a)

[0038] Take 1.51g of 2-mercaptobenzoxazole, mix it with 10mL of water, add 30% KOH dropwise until the solid is completely dissolved, pour it into the above-mentioned sodium ethyl thiosulfate solution, continue to stir at room temperature for 30min, and evaporate under reduced pressure. Part of the ethanol was extracted with ether, dried over magnesium sulfate, concentrated by filtration, and the residue was subjected to silica gel column chromatography (petroleum ether and ether as eluents) to obtain a colorless oil. Yield 75%.

[0039] 1 H-NMR (CDCl 3 ), δ (ppm): 1.43 (t, 3H, CH 3 ), 3.02(q, 2H, CH 2 ), 7.30(m, 2H, ArH), 7.50(m, 1H, ArH), 7.68(m, H, ArH); ESI-Mass: 211.9(M+1) + .

Embodiment 3

[0040] Embodiment 3, the preparation of ethyl-(2-benzothiazole) disulfide (1b)

[0041] Referring to Example 2, just change 2-mercaptobenzoxazole into 2-mercaptobenzothiazole. The product is a colorless oil with a yield of 70%; 1 H-NMR (CDCl 3 ), δ (ppm): 1.41 (t, 3H, CH 3 ), 2.98(q, 2H, CH 2 ), 7.30 (m, 2H, ArH), 7.42 (m, H, ArH), 7.79 (dd, H, ArH), 7.86 (dd, H, ArH); ESI-Mass: 227.9 (M+1) + .

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Abstract

The invention belongs to the fields of organic chemistry and pharmaceutical chemistry and particularly relates to novel disulfide compounds shown as a formula I as well as a synthetic method and application of the novel disulfide compounds. The disulfide compounds have strong inhibiting function for various tumor cells and can be used as pilot compounds for researching novel tumor-resisting medicaments or can be used as medicaments for treating various clinically-general multiple cancers. The formula I is shown as the description.

Description

technical field [0001] The invention belongs to the fields of organic chemistry and medicinal chemistry. Specifically, the present invention relates to a novel disulfide compound with antitumor activity and a new synthesis method and use thereof. These compounds have a strong inhibitory effect on a variety of tumor cells, and can be used as a class of lead compounds for the development of new anti-tumor drugs, and may also be used as drugs for various common clinical multiple cancers. technical background [0002] The death rate caused by malignant tumors ranks second among all diseases, second only to cardiovascular and cerebrovascular diseases. Clinically used antineoplastic drugs generally have the disadvantages of high toxicity and side effects, and easy drug resistance. Therefore, it is the goal of medicinal chemists to find drugs with better curative effect, lower toxicity and side effects, and wider anti-tumor spectrum. [0003] Disulfide compounds show good biolog...

Claims

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Application Information

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IPC IPC(8): C07D263/58C07D277/78C07D235/28A61K31/423A61K31/428A61K31/4184A61P35/00
Inventor 郭跃伟李佳龚景旭盛丽姚励功周宇波
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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