2-amino-7-substituted benzothiazole compound as well as preparation method and application thereof

A technology of benzothiazole and compounds, applied in the field of medicinal chemistry, can solve the problems of high cost, high medical expenses, and unsatisfactory effects, and achieve the effects of simple post-processing, high yield, and short reaction steps

Active Publication Date: 2015-04-01
ZHANGZHOU PIEN TZE HUANG PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hepatitis and liver cancer patients suffer from serious diseases all the year round, and the medical expenses are extremely high. Currently, the interferon, interleukin and antiviral drugs used to treat hepatitis and liver cancer are expensive, but the effect is not satisfactory, which causes economic losses to individuals and society. Therefore, it is of great significance to develop new drugs for the treatment of hepatitis and liver fibrosis

Method used

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  • 2-amino-7-substituted benzothiazole compound as well as preparation method and application thereof
  • 2-amino-7-substituted benzothiazole compound as well as preparation method and application thereof
  • 2-amino-7-substituted benzothiazole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The synthesis of embodiment 1 2-amino-7-methylbenzothiazole

[0057] Dissolve 0.03mmol of 3-methylaniline in 12mL of acetic acid, add 30mmol of potassium thiocyanate and stir for 20 minutes. 5 mmol of bromine was dissolved in 0.3 mL of acetic acid, slowly added to the above-mentioned reactant, the reaction temperature in a water bath was 35°C, stirred overnight, filtered, and the precipitate was washed twice with 30 mL of ethyl acetate. Combine the filtrate and washing liquid, alkalinize it with ammonia solution, wash it 4 times with 50 mL concentrated brine, concentrate to 30 mL, apply flash chromatography, elute with n-hexane: acetone 4:1 (v / v), collect the eluate , and the solvent was evaporated to obtain 3.0 g of 2-amino-7-methylbenzothiazole with a yield of 61%. 1 H-NMR (CDCl 3 , 500MHz): δ2.38(m, 3H), 4.08(brs, 2H), 7.40(dd, J=8.6HzJ=2.3Hz, 1H), 7.49(d, J=2.3Hz, 1H), 7.68(d , J=8.6Hz, 1H); ESI-MS (m / z, %): 163.04 (M-H) - .

Embodiment 2

[0058] Example 2 Synthesis of 2-amino-7-ethylbenzothiazole

[0059] Dissolve 0.02mmol of 3-ethylaniline in 14mL of acetic acid, add 40mmol of potassium thiocyanate and stir for 15 minutes. 7mmol of bromine was dissolved in 0.4mL of acetic acid, slowly added to the above-mentioned reactant, the reaction temperature in a water bath was 40°C, stirred overnight, filtered, and the precipitate was washed 5 times with 10mL of ethyl acetate. Combine the filtrate and washing liquid, alkalinize it with ammonia solution, wash it with 60mL concentrated brine four times, concentrate to 20mL, apply flash chromatography, elute with n-hexane: acetone 6:1 (v / v), collect the eluate , and the solvent was evaporated to obtain 2.06 g of 2-amino-7-ethylbenzothiazole with a yield of 58%. 1 H-NMR (CDCl 3, 500MHz), δ1.02(t, J=2.4Hz, 3H), 2.06(m, 2H), 4.28(brs, 2H), 7.42(dd, J=8.0Hz, J=2.1Hz, 1H), 7.49 (d, J=2.1Hz, 1H), 7.65 (d, J=8.0Hz, 1H); ESI-MS (m / z, %): 177.06 (M-H) - .

Embodiment 3

[0060] Example 3 Synthesis of 2-amino-7-methoxybenzothiazole

[0061] Dissolve 0.04mmol of 3-methylaniline in 16mL of acetic acid, add 50mmol of potassium thiocyanate and stir for 10 minutes. 9 mmol of bromine was dissolved in 0.5 mL of acetic acid, slowly added to the above-mentioned reactant, the reaction temperature in a water bath was 30°C, stirred overnight, filtered, and the precipitate was washed 3 times with 20 mL of ethyl acetate. Combine the filtrate and washing liquid, alkalinize it with ammonia solution, wash it three times with 80 mL concentrated brine, concentrate to 40 mL, apply flash chromatography, elute with n-hexane: acetone 4:1 (v / v), collect the eluate , and the solvent was evaporated to obtain 5.32 g of 2-amino-7-methoxybenzothiazole with a yield of 64%. 1 H-NMR (CDCl 3 , 500MHz), δ2.32(s, 3H), 4.20(brs, 2H), 7.06(dd, J=8.3Hz, J=2.2Hz, 1H), 7.40(d, J=2.2Hz, 1H), 7.54 (d, J=8.3Hz, 1H); ESI-MS (m / z, %): 207.03 (M-H) - .

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Abstract

The invention belongs to the field of medicine chemistry, and particularly relates to a 2-amino-7-substituted benzothiazole compound as well as a preparation method and application thereof. The 2-amino-7-substituted benzothiazole compound can be used for remarkably inhibiting synthesis of activated rat liver star-shaped cell collagen I type and extracellular matrix and regulating the expression of relevant synthetic gene and enzyme, has an obvious inhibition effect on generation of mouse liver fibrosis model cell periplasm, and can be used as a medicine for resisting hepatitis and liver fibrosis. The preparation method of the 2-amino-7-substituted benzothiazole compound adopts raw materials which are wide in source, and is short in reaction steps, simple and convenient in after-treatment and relatively high in yield.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to 2-amino-7-substituted benzothiazole compounds and a preparation method and application thereof. Background technique [0002] Liver disease is one of the diseases that seriously threaten human health. According to the etiology, it can be roughly divided into infectious liver disease and non-infectious liver disease. Infectious liver diseases include: hepatitis B (HBV), hepatitis C (HCV) and hepatitis D (HDV), liver diseases caused by schistosomiasis, etc.; non-infectious liver diseases include: congenital metabolic defects (hepatolenticular degeneration , hemochromatosis, α1-antitrypsin deficiency, etc.), liver disease caused by chemical metabolic defects (chronic alcoholic liver disease, chronic drug-induced liver disease), autoimmune hepatitis, primary liver cirrhosis , Primary sclerosing cholangitis, etc. [0003] According to statistics, hepatitis is one of t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/82A61K31/428A61P1/16A61P31/14A61P31/20
CPCC07D277/82
Inventor 黄进明陈志亮曾金香殷婷婷
Owner ZHANGZHOU PIEN TZE HUANG PHARM
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