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1,2,3-thiadiazole compounds, and their preparing process and bioactivity

A technology of thiadiazoles and compounds, which is applied in the field of preparation of thiadiazoles, can solve the problems of limited application, high cost, serious drug damage, etc., and achieve good inhibitory effect, novel structure, and easy synthesis

Inactive Publication Date: 2002-05-01
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to prevent and treat plant viruses, people have carried out various studies. Since Schuster discovered that triazine compounds (DHT) have a good inhibitory effect on plant viruses in the 1970s, chemists have found that many compounds have good inhibitory effects so far. Inhibition of plant virus activity, such as ribin, ribavirin, citrinin, purine and pyrimidine, plant hormones and some natural antiviral substances, however they also have different problems that limit their application
For example, knitrin has no systemic property and cannot be absorbed by tissues; ribavirin has the disadvantages of short duration of action, serious drug damage and high cost; pyrimidine and purine also have the problem of serious drug damage, and are sometimes completely ineffective; and Phytohormone drugs mainly stimulate the growth of crops and have no effect on the proliferation of viruses

Method used

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  • 1,2,3-thiadiazole compounds, and their preparing process and bioactivity
  • 1,2,3-thiadiazole compounds, and their preparing process and bioactivity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of α-Chloroacetoacetylmethylamide-N-Ethoxycarbonylhydrazone

[0035] Dissolve 21 g (90%) (0.125 mol) of α-chloroacetoacetamide in 60 mL of absolute ethanol, slowly add 12.9 g (0.125 mol) of ethyl carbazate dropwise at room temperature, react at room temperature for 18 h, and remove in vacuo Part of the solvent was removed and recrystallized to obtain 21 g of a white solid with a yield of 71% and a melting point of 120-121°C. Elemental analysis: found, C: 40.78, H: 5.51, N: 17.64; calculated: C: 40.77, H: 5.99, N: 17.83. 1 H NMR (CDCl 3 ): 1.30 (t, J=7.2, 3H, CH 3 ), 1.90 (s, 3H, CH 3 ), 2.87 (d, J=4.6, 3H, NCH 3 ), 4.25 (q, J=7.0, 2H, OCH 2 ), 5.11 (s, 1H, CH), 6.76 (br, 1H, NH), 7.90 (br, 1H, NH).

Embodiment 2

[0037] Synthesis of α-chloro-1,2,3-thiadiazole acetamide

[0038] Add 25mL of thionyl chloride to the reaction flask, cool to 5°C, add 21g of the product from the previous step into the reaction flask in batches under stirring, and control the temperature not to exceed 10°C. In the sodium saturated aqueous solution, a large amount of solids were precipitated, filtered by suction, and recrystallized with ethanol to obtain 14.5 g of the product, the yield was 85%, and the melting point was 144-145°C. Elemental analysis: found, C: 31.45, H: 2.89, N: 21.77; calculated: C: 31.34, H: 3.16, N: 21.93. 1 HNMR (CDCl 3 ): 2.93 (d, J=4.8, 3H, NCH 3 ), 5.91 (s, 1H, CH), 6.96 (br, 1H, NH), 8.67 (s, 1H, thiadiazole-H).

Embodiment 3

[0040] Synthesis of α-substituted phenoxy-1,2,3-thiadiazole acetamide (II-3a)

[0041] Dissolve 0.87 g (4 mmol) of p-bromophenol in 10 mL of methanol, add 0.24 g (5 mmol) of sodium hydroxide, stir at room temperature for 10 minutes, then add 0.77 g of α-chloro-1,2,3-thiadiazole acetamide g (4 mmol), stirred at room temperature for 48 h, evaporated the solvent in vacuo, washed the solid with 10 mL of water, filtered with suction, and decompressed the residue on a silica gel column with eluent ethyl acetate / petroleum ether (v:v=1:5) Rinse and wash to obtain 0.6g of pure product.

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Abstract

The present invention relates to a process for preparing 1,2,3-thiadiazole compounds, which can be used to prevent and treat hepatitis B and plant viruses.

Description

technical field [0001] The invention relates to the preparation of thiadiazole compounds, which can be used in the treatment and / or prevention of hepatitis B and in the prevention and treatment of plant viruses in agriculture. Background technique [0002] Hepatitis B Virus (HBV) is a considerable public health problem because of the virus' ability to cause acute and chronic infections. Chronic HBV infection can lead to cirrhosis and primary hepatocellular carcinoma. Although HBV vaccines have been available for many years, there is currently no effective treatment that can successfully control chronic HBV infection. There are still 300 million people in the world infected with HBV, of which China accounts for 75%, and they cannot benefit from the existing commercial vaccines. The efficacy of the existing HBV treatment methods is not enough, or there are serious side effects, such as interferon, which is recognized as having a clear curative effect, only has an effective r...

Claims

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Application Information

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IPC IPC(8): A01N43/828C07D285/06
Inventor 李正名赵卫光杨炤
Owner NANKAI UNIV
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