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Tetrahydrobenzothiazol-2-acetone oxime derivative and preparation method and application thereof

A technology of benzothiazole and acetone oxime, which is applied in the field of compounds and their preparation, to achieve the effects of cheap and easy-to-obtain reaction raw materials, high yield, and short steps

Active Publication Date: 2018-04-03
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The invention provides a derivative of tetrahydrobenzothiazole-2-acetone oxime and its preparation method and application, so as to solve the problem of antitumor effect of thiazole derivatives

Method used

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  • Tetrahydrobenzothiazol-2-acetone oxime derivative and preparation method and application thereof
  • Tetrahydrobenzothiazol-2-acetone oxime derivative and preparation method and application thereof
  • Tetrahydrobenzothiazol-2-acetone oxime derivative and preparation method and application thereof

Examples

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Embodiment 1

[0034] A tetrahydrobenzothiazole-2-acetone oxime derivative (compound 1a), namely 3-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)-1-(4- Methylphenyl)-1-acetone oxime, its structural formula is as follows:

[0035]

[0036] The synthetic route of compound 1a is as follows:

[0037]

[0038] The specific synthetic method of compound 1a comprises the following steps:

[0039] (1) Synthesis of thioformamide: In a 100mL round bottom flask, add 7.25mL (182mmol) formamide and dissolve it in 50mL 1,4-dioxane, then add 8.65g (38.85mL) in batches within 30min mmol) phosphorus pentasulfide, heated in an oil bath to 100°C for 2h under stirring. After the reaction was completed, the reaction liquid was cooled to room temperature, and the obtained solution was poured into a dry flask, concentrated, and the product was directly used in the next reaction without purification.

[0040] (2) Synthesis of compound 3a (1-(4-methylphenyl) cyclopropanol): In a 250mL four-neck flask, add 1.50g (1...

Embodiment 2

[0045] A derivative of tetrahydrobenzothiazole-2-acetone oxime (compound 1s), that is, 3-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)-1-(3- Chlorine 4-methylphenyl)-1-acetone oxime, its structural formula is as follows:

[0046]

[0047] The synthetic route of compound 1s is as follows:

[0048]

[0049] The specific synthetic method of compound 1s comprises the following steps:

[0050] (1) Synthesis of thioformamide: as shown in Example 1.

[0051] (2) Synthesis of compound 3s (1-(3-chloro-4-methylphenyl) cyclopropanol): In a 250mL four-neck flask, add 10mmol of compound 2s, dissolve it in 50mL of anhydrous tetrahydrofuran, and then add 3.82 mL (14 mmol) isopropyl titanate. The mixture was cooled to 0° C. under an ice bath, and 13.98 mL (28 mmol) of a solution of 2M ethylmagnesium bromide dissolved in tetrahydrofuran was added dropwise under nitrogen protection, and the addition was completed within 30 minutes. The reaction solution was raised to room temperature for 2...

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Abstract

The invention discloses a tetrahydrobenzothiazole-2-acetone oxime derivative, and a preparation method and application thereof. A structural formula is shown in the description. R is any one of the following radical groups: 4-methylphenyl, phenyl, 2-methylphenyl, 3-methylphenyl, 2,5-dimethylphenyl, 3,5-dimethylphenyl, 4-n-propylphenyl, 4-tert-butylphenyl, 4-methoxyphenyl, 3-methoxyphenyl, 3,4,5-trimethoxyphenyl, 3-biphenyl, 4-trifluoromethoxyphenyl, 3-fluorophenyl, 4-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 3,5-bis(trifluoromethyl)phenyl, 3-chloro-4-methylphenyl, 3-furyl, 3-thienyl, 2-pyridyl, 4-pyridyl, 2-quinolyl, and 6-quinolyl. The tetrahydrobenzothiazol-2-acetone oxime derivative has relatively high antitumor activity and is suitable for preparing antitumor drugs. The preparationmethod of the derivative has the characteristics of cheap and readily available raw materials, short steps, and high reaction efficiency.

Description

technical field [0001] The invention relates to a compound and a preparation method thereof, in particular to a tetrahydrobenzothiazole-2-acetone oxime derivative and a preparation method and application thereof. Background technique [0002] Cancer is a malignant disease caused by the body's inability to control the unlimited proliferation of cells. In China, due to factors such as smoking, hepatitis B infection, population aging, and environmental pollution, the incidence and mortality of cancer continue to increase. "Cancer statistics in China, 2015" released by Prof. Chen Wanqing, Academician of Cancer Hospital, Chinese Academy of Medical Sciences, and National Cancer Center, shows that cancer has become the leading cause of death in China, and the cancers with the highest morbidity and mortality are lung cancer, gastric cancer, The morbidity and mortality of esophageal cancer and liver cancer follow closely. [0003] Chemotherapy has always played a dominant role in t...

Claims

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Application Information

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IPC IPC(8): C07D277/60A61P35/00
CPCC07D277/60
Inventor 李洪爽张瑞泽夏成才段桂运
Owner TAISHAN MEDICAL UNIV
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