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Myricetin derivative containing amide thioether thiadiazole, and preparation method and application of same

A technology containing amide sulfides and thiadiazoles, which can be used in botany equipment and methods, chemicals for biological control, biocides, etc., and can solve problems such as instability, unfavorable absorption and release, and influence on drug efficacy

Active Publication Date: 2018-01-19
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In 2012, Yu et al. (Yu, M.S.; Lee, J.; Lee, J.M.; Kim, Y.; Chin, Y.W.; Jee, J.G.; Keum, Y.S.; Jeong, Y.J. Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13[J].Bioorg.med.chem.lett.,2012,22(12):4049-4054.) by performing a double-stranded DNA unwinding assay with fluorescence resonance energy transfer (FRET) or using a colorimetric Based on the hydrolysis test method, the inhibitory effect of myricetin on SARS virus in vitro was studied. The study found that: myricetin potentially inhibited the SARS virus helicase protein and affected the activity of ATPase, but it had no unwinding activity, and myricetin Does not exhibit cytotoxicity against normal mammary epithelial MCF10A cells
However, myricetin and its derivatives have less research on pesticides. At the same time, due to the special structural characteristics of myricetin, its water solubility and fat solubility are relatively poor, which is not conducive to absorption and release, and affects the performance of the drug; it is unstable and difficult to produce. save

Method used

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  • Myricetin derivative containing amide thioether thiadiazole, and preparation method and application of same
  • Myricetin derivative containing amide thioether thiadiazole, and preparation method and application of same
  • Myricetin derivative containing amide thioether thiadiazole, and preparation method and application of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] 3-O-(N-(5-((ethyl)mercapto)-1,3,4-thiadiazol-2-yl)-acetamido-2-yl)-3',4',5', 5,7-pentamethoxymyricetin (target compound A 1 ) preparation method, comprising the following steps:

[0050] (1) Preparation of 2-amino-5-mercapto-1,3,4-thiadiazole

[0051] Add 1.03g (11.30mmol) of thiosemicarbazide and 0.78g of anhydrous (5.65mmol) potassium carbonate into a 100mL single-necked round bottom flask, add 30mL of ethanol to dissolve the thiosemicarbazide, heat and stir to reflux to boiling. 1.03g (13.56mmol) of carbon disulfide was converted into a volume of 818μL and dissolved in a 10mL measuring cup filled with 5mL of absolute ethanol, and the ethanol solution of carbon disulfide was slowly added dropwise to the reaction system, and continued to reflux for 4h. TLC traced the end of the reaction, stopped the reaction, evaporated the solvent under reduced pressure, added 30 mL of water to the residue, stirred for 10 min, acidified with 10% hydrochloric acid, filtered and washe...

Embodiment 2

[0061] 3-O-(N-(5-((phenyl)mercapto)-1,3,4-thiadiazol-2-yl)-acetamido-2-yl)-3',4',5', 5,7-pentamethoxymyricetin (target compound A 2 ) preparation method, comprising the following steps:

[0062] (1) Preparation of 2-amino-5-mercapto-1,3,4-thiadiazole:

[0063]As in the first (1) step of Example 1.

[0064] (2) Preparation of 2-amino-5-((phenyl)mercapto)-1,3,4-thiadiazole

[0065] As in the (2) step of Example 1, the difference is that benzyl chloride is used as a raw material.

[0066] (3) Preparation of N-(5-((phenyl)mercapto)-1,3,4-thiadiazol-2-yl)-2-chloro-acetamide

[0067] As in step (3) of Example 1, the difference is that 2-amino-5-((phenyl)mercapto)-1,3,4-thiadiazole is used as the raw material.

[0068] (4) Preparation of 3-hydroxy-3',4',5',5,7-pentamethoxymyricetin

[0069] As embodiment 1 (4) step.

[0070] (5) 3-O-(N-(5-((phenyl)mercapto)-1,3,4-thiadiazol-2-yl)-acetamide-2-yl)-3',4', Preparation of 5',5,7-pentamethoxymyricetin.

[0071] As in step (5) of E...

Embodiment 3

[0073] 3-O-(N-(5-((2-chlorophenyl)mercapto)-1,3,4-thiadiazol-2-yl)-acetamido-2-yl)-3',4', 5',5,7-pentamethoxymyricetin (target compound A 3 ) preparation method, comprising the following steps:

[0074] (1) Preparation of 2-amino-5-mercapto-1,3,4-thiadiazole:

[0075] As in the first (1) step of Example 1.

[0076] (2) Preparation of 2-amino-5-((2-chlorophenyl)mercapto)-1,3,4-thiadiazole

[0077] As in step (2) of Example 1, the difference is that 2-chlorobenzyl chloride is used as a raw material.

[0078] (3) Preparation of N-(5-((2-chlorophenyl)mercapto)-1,3,4-thiadiazol-2-yl)-2-chloro-acetamide

[0079] As in step (3) of Example 1, the difference is that 2-amino-5-((2-chlorophenyl)mercapto)-1,3,4-thiadiazole is used as the raw material.

[0080] (4) Preparation of 3-hydroxy-3',4',5',5,7-pentamethoxymyricetin

[0081] As embodiment 1 (4) step.

[0082] (5) 3-O-(N-(5-((2-chlorophenyl)mercapto)-1,3,4-thiadiazol-2-yl)-acetamide-2-yl)-3', Preparation of 4',5',5,7-pentame...

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Abstract

The invention discloses a myricetin derivative containing amide thioether thiadiazole, of which a general formula is represented as follows, wherein R is hydrocarbyl groups, phenyl groups, substituted phenyl groups, heteroaromatic ring groups or substituted heteroaromatic ring groups. The compound has high treatment and prevention effect against tobacco mosaic virus (TMV), has high anti-plant virus activity and can be used for preparing anti-plant virus pesticides. The compound has high inhibition activity on Xanthomonas axonopodis and Xanthomonas oryzae and can be used for preparing agricultural bactericides.

Description

technical field [0001] The invention relates to the technical field of chemical engineering, in particular to a preparation method of a myricetin derivative containing amide thioether thiadiazole and its application in the aspects of anti-plant virus and anti-phytobacteria. Background technique [0002] Flavonols, as secondary metabolites in organisms, are widely distributed in nature, and have attracted extensive attention at home and abroad because of their diverse physiological activities. At present, the biological activity research of flavonol compounds mainly focuses on the cardiovascular system, anti-virus, anti-inflammatory and anti-tumor effects. [0003] Myricetin (3',4',5',3,5,7-hexahydroxyflavonol, Myricetin (Myr)), synonymous myricetin, myricetin, myricetin, is a natural flavonoid and polyphenol These compounds are usually found in the fruits, vegetables, tea and beverages we eat every day. Most exist in the form of glycosides, not in the form of free glycosid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D417/14A01N43/824A01P1/00A01P3/00
Inventor 薛伟阮祥辉陈丽娟王一会李普张橙张菊平李琴王俊
Owner GUIZHOU UNIV
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