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1-substituted-4,4-2 substituted thiosemicarbazide compounds, production method and uses of the same

A technology of thiosemicarbazide and compound, applied in the fields of medicinal chemistry and pharmacotherapy, can solve problems such as insufficient comprehensiveness

Inactive Publication Date: 2008-06-11
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

[0007] Although the research on thiosemicarbazones has made great progress, it is not comprehensive enough, and the long-chain thiosemicarbazones are rarely involved.
In addition, there is no systematic research on fused ring thiosemicarbazone compounds

Method used

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  • 1-substituted-4,4-2 substituted thiosemicarbazide compounds, production method and uses of the same
  • 1-substituted-4,4-2 substituted thiosemicarbazide compounds, production method and uses of the same
  • 1-substituted-4,4-2 substituted thiosemicarbazide compounds, production method and uses of the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0287] 1) 2-(2-ethoxy-2-thioethylcarbonyl)acetic acid (V-1)

[0288] Measure 25 ml of ethanol as a reactant and solvent, add it to a 50 ml eggplant-shaped bottle; weigh 3 grams of thiodiglycolic anhydride and add it to an eggplant-shaped bottle, stir at room temperature, and after 10 hours of reaction, evaporate most of the excess under reduced pressure ethanol, and pumped on the oil pump for one hour, 3.52 g of oily product V-1 were obtained without further purification.

[0289] 2) 2-(2-ethoxy-2-thioethylcarbonyl)acetyl chloride (VI-1)

[0290] Dissolve 3.5 g of 2-(2-ethoxy-2-thioethylcarbonyl)acetic acid V-1 in 15 ml of dichloromethane, stir in an ice bath, slowly add 8 ml of redistilled dichloromethane After the addition of sulfone, the ice bath was removed. After reacting for 8 hours, the solvent and excess thionyl chloride were distilled off under reduced pressure to obtain 3.64 g of yellow oily product VI-1, which was not further purified.

[0291] 3) Ethyl 2-[2-(4-m...

Embodiment 2

[0300] 1-{2-[2-(4-Methoxyanilino)-2-thioethylcarbonyl]acetyl}-4-(4-nitrophenyl)-thiosemicarbazide (I A -2)

[0301] 2-formic acid methyl phenyl isothiocyanate is replaced by 4-nitrophenyl isothiocyanate, and all the other required raw materials, reagents and preparation methods are the same as in Example 1 to obtain yellow solid I A -2, yield 67.1%.

[0302] 1 H-NMR (400Hz, DMSO-d6) δ: 8.18 (2H, d), 7.87 (2H, d), 7.43 (2H, d), 6.84 (2H, d), 3.69 (3H, s), 3.43 (4H , s).

Embodiment 3

[0304] 1-{2-[2-(4-methoxyanilino)-2-thioethylcarbonyl]acetyl}-4-(1-naphthyl)-thiosemicarbazide (I A -3)

[0305] 2-formic acid methyl phenyl isothiocyanate is replaced by 1-naphthyl isothiocyanate, and all the other required raw materials, reagents and preparation methods are the same as in Example 1 to obtain white solid I A -3, yield 80%.

[0306] 1 H-NMR (400Hz, DMCO-d6) δ: 7.95 (2H, t), 7.86 (1H, d), 7.51 (3H, m), 7.36 (3H, d), 6.78 (2H, d), 3.78 (3H , s), 3.48 (2H, s), 3.47 (2H, s). MS-ESI: 453.2 (M-H), 455.0 (M+H), 477.1 (M+Na).

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Abstract

The invention relates to a 1-substituted-4, 4-bis-substituted thiosemicarbazide compound, a relative preparation method and application thereof, wherein the compound is represented as formula I, R1, R2 and R3 are defined as description. The inventive compound can restrain A-549 (human lung adenocarcinoma), P388 (mouse leukemia cell line), and HT-29 (human intestinal cancer cell line), with strong inhibition of cell proliferation, which can be used to develop new anti-cancer drug.

Description

technical field [0001] The present invention relates to the fields of medicinal chemistry and pharmacotherapeutics. Specifically, the present invention relates to 1-substituted-4,4-disubstituted thiosemicarbazide compounds, their preparation methods and their uses. Background technique [0002] Tumor is a disease that seriously endangers health. Among various diseases, the mortality rate of malignant tumors ranks second, second only to cardiovascular and cerebrovascular diseases. Since the 1970s, the incidence of malignant tumors has been increasing at an annual rate of 3% to 5%. According to statistics, more than 6 million patients die of malignant tumors all over the world every year, and nearly 6 million people develop tumors every year. Therefore, searching for highly effective, low-toxic, and cheap anticancer drugs has become a research hotspot for medical workers worldwide. [0003] The thiosemicarbazone compounds have attracted the attention of medical workers beca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C335/20C07D215/12C07D241/42C07D333/58C07D495/04A61K31/145A61K31/381A61K31/498A61K31/47A61P35/00
Inventor 柳红蒋华良丁健林莉萍黄河罗小民朱维良沈建华陈凯先
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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