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Benzothiadiazole compound and application in plant cell thereof

A technology for benzothiadiazoles and compounds is applied in the field of benzothiadiazole compounds, which can solve the problems of lack of resources, slow growth of Taxus chinensis, etc.

Inactive Publication Date: 2005-05-18
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, yew grows slowly in nature and its resources are increasingly scarce

Method used

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  • Benzothiadiazole compound and application in plant cell thereof
  • Benzothiadiazole compound and application in plant cell thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Synthesis of 7-carboxybenzo-1,2,3-thiadiazole trifluoroethyl ester (compound 1):

[0018] Mix 7-carboxybenzothiadiazole (3.3mmol) and 8ml thionyl chloride, add a drying tube and a tail gas absorption device, heat the oil bath to 80-100°C, and keep it for 7-8 hours. After cooling to room temperature, the unreacted thionyl chloride was distilled off under reduced pressure to obtain a somewhat sticky solid, which was dissolved in toluene for further use. Measure 4ml of trifluoroethanol and 4ml of dry toluene and mix them in a small flask, add triethylamine, slowly add acid chloride toluene solution dropwise under stirring. Stir at room temperature for 2-4 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate and washed with NaHCO 3 Wash once with saturated solution, twice with water, anhydrous MgSO 4 dry. Filter and concentrate to obtain a yellow-brown solid, which is separated by 300-400 mesh silica gel column chromatography. The obtaine...

Embodiment 2

[0022] Synthesis of benzo-1,2,3-thiadiazole-7-carboxylic acid-2,2,3,3,3-pentafluoropropyl ester (compound 2):

[0023] The acid chloride prepared by 7-carboxybenzothiadiazole (2.2mmol) (the preparation of the acid chloride is the same as in Example 1) was dissolved in toluene, and was added dropwise to a solution composed of pentafluoropropanol, toluene and triethylamine under stirring , the dropwise addition time is about 1 hour. The reaction was continued at room temperature for 5 hours. Pour the reaction mixture into water, extract with ethyl acetate, dilute K 2 CO 3 Solution washing, water washing, anhydrous MgSO 4 dry. Filtrate and concentrate to obtain a brown solution, which was separated by 300-400 mesh silica gel column chromatography to obtain 0.23 g of light yellow prismatic crystals, with a yield of 33.5% and a melting point of 79-80°C.

[0024] 1 HNMR (SF: 500MHz, DMSO-d 6 )δ (ppm): 9.10-9.12 (d, 1H, J = 8.12Hz), 8.44-8.45 (d, 1H, J = 7.32Hz), 7.98-8.01 (t,...

Embodiment 3

[0026] Synthesis of benzo-1,2,3-thiadiazole-7-carboxylic acid-pentafluorobenzyl ester (compound 3)

[0027] Other reaction conditions are the same as in Example 1 except pentafluorobenzyl alcohol. Obtained 0.42 g of pale yellow needle-like crystals with a yield of 53.0% and a melting point of 146-7°C.

[0028] 1 HNMR (SF: 500MHz, DMSO-d 6 )δ (ppm): 9.03-9.05 (d, 1H, J = 8.10Hz), 8.39-8.41 (d, 1H, J = 7.35Hz), 7.91-7.94 (t, 1H, J 1 =7.65Hz,J 2 =7.83Hz), 5.62(s, 2H). HRMS, M + (m / e) 359.9983 (calc. 369.9992).

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Abstract

The present invention discloses a kind of diazosulfide new compound structure and its application for promoting plant cell secondary metabolic product growth. Said invention selects and uses taxus chinensis cell as application system, and proceeds from structure of immunoactivating agent thiobiazole to design and synthesize new type plant cell inductive activating agent. The test results show that the capacity of said invented benzothiobiazole compound for promoting production of taxane is similar to or higher than that of existent methyl jasmonate.

Description

technical field [0001] The present invention relates to a class of benzothiadiazole compounds and uses thereof. Background technique [0002] The abundant plant resources in nature contain a considerable amount of secondary metabolites, including many expensive pharmaceuticals. In order to develop these valuable resources, in addition to extraction from plant raw materials or possible chemical synthesis, large-scale cultivation of plant cells in vitro is also an effective way. The use of elicitors to regulate secondary metabolites has attracted the attention of more and more scholars at home and abroad, and has become one of the important methods to greatly increase the content and yield of metabolites in cultures (Xie Qiuling, Guo Yong, Food Science, 1998, 19(10), 7-9). [0003] The elicitors currently used in plant cell culture mainly include: (1) Glycoproteins: as adding glycosylated oxidized bovine serum albumin (BSA) and oxidized lysozyme to the medium, tobacco leaves...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/14C12N5/04
Inventor 钱旭红钟建江赵振江钱志刚徐玉芳田文红
Owner EAST CHINA UNIV OF SCI & TECH
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