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Thiazole-containing flavonoid derivatives as well as preparation method and application thereof

A technology for flavonoids and derivatives, which is applied in the fields of organic synthesis chemistry and pesticides, and achieves the effects of high yield, good inhibitory activity, and easy availability of raw materials

Pending Publication Date: 2022-02-01
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, flavonoids and thiazoles have broad-spectrum biological activities, but in the prior art, there is no technical solution for splicing the active substructures of flavonoids and thiazoles

Method used

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  • Thiazole-containing flavonoid derivatives as well as preparation method and application thereof
  • Thiazole-containing flavonoid derivatives as well as preparation method and application thereof
  • Thiazole-containing flavonoid derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 3 - Preparation of ((2-chlorothiazol-5-yl) methoxy) -2-phenyl-4H-色-4-ketone (Ia)

[0022]

[0023] The o-hydroxybenzophenone and benzaldehyde were dissolved in methanol, and a solution of aqueous sodium hydroxide of 30% by weight was added dropwise to stir for 2 hours at room temperature. After the reaction is completed, the reaction system is slowly added dropped to the reaction hydrochloric acid to make it pH = 3, the reaction liquid filtration, the solid collection, drying, to obtain intermediate Turlketone; dissolve Charlone in ethanol, 0 ° C, 0.2 ° C The concentration of 20% aqueous sodium hydroxide solution and a mass concentration of 30% hydrogen peroxide, room temperature reaction for 12 hours. After the reaction is completed, the concentrated hydrochloric acid is slowly added dropwise to the reaction system, and the reaction liquid is filtered, the solid is collected, dried to obtain intermediate 3-hydroxy-2-phenyl-4H-ortho-4-ketone; Soluble in acetonitrile, 2-ch...

Embodiment 2

[0025] Preparation of 2- (2-chlorophenyl) -3- (2-chlorothiazole-5-yl) methoxy) -4H-orthol-4-ketone (Ib)

[0026]

[0027] The preparation method is in Example 1, and benzamine is converted to 2-chlorobenzaldehyde to obtain a compound product Ib. White solid, yield 89%; 1 H NMR (400MHz, CDCL 3 Δ8.32 (D, J = 7.9 Hz, 1H), 7.71 (T, J = 7.8 Hz, 1H), 7.55-7.43 (M, 4H), 7.42-7.34 (M, 2H), 7.26 (s, 1h) ), 5.27 (s, 2h); 13 C NMR (100MHz, CDCL 3 Δ174.7, 156.3, 155.6, 153.5, 141.0, 139.1, 136.2, 133.9, 133.7, 131.6, 131.5, 130.0, 129.7, 126.6, 118.8, 65.3; HRMS (ESI-TOF) M / Z: [ M + NA] + Calcd forc 19 Hide 11 CL 2 Nnao 3 S 425.9729, Found 425.9728.

Embodiment 3

[0029] Preparation of 2- (3-chlorophenyl) -3- (2-chlorothiazole-5-yl) methoxy) -4H-orthol-4-ketone (IC)

[0030]

[0031] The preparation method is in Example 1, and benzamine is converted to 3-chlorobenzoformhyde to obtain a compound product Ic. White solid, yield 93%; 1 H NMR (400MHz, CDCL 3 Δ8.27 (D, J = 7.9 Hz, 1H), 7.94 (S, 1H), 7.84 (D, J = 7.7 Hz, 1H), 7.72 (T, J = 7.7 Hz, 1H), 7.55 (D, J = 8.4 Hz, 1H), 7.51-7.40 (m, 3H), 7.36 (S, 1H), 5.32 (S, 2H); 13 C NMR (100MHz, CDCL 3 Δ174.7, 155.2, 155.0, 153.6, 141.4, 138.9, 135.8, 134.6, 134.0, 132, 134.8, 129.8, 128.7, 126.9, 118.1, 65.2, 123.9, 118.1, 65.2; HRMS (ESI-TOF) M / Z: [ M + NA] + Calcd for c 19 Hide 11 CL 2 Nnao 3 S 425.9729, Found 425.9721.

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Abstract

The invention relates to thiazole-containing flavonoid derivatives as well as a preparation method and application thereof, belonging to the technical field of organic synthesis in the chemical industry. The structural formula of the thiazole-containing flavonoid derivatives is as shown in (I) which is described in the specification. According to the preparation method, flavone and thiazole structures are subjected to substructure splicing, and a series of thiazole-containing flavone derivatives are designed and synthesized. The derivatives can resist plant pathogenic fungi, have good inhibitory activity, can be processed into missible oil, microemulsions, emulsion in water, suspending agents or wettable powder and the like, and are used for preventing and treating plant diseases such as rhizoctonia solani, fusarium graminearum, gaeumannomyces graminis, alternaria solani, strawberry gray mold and cylindrosporium pomi Brooks.

Description

Technical field [0001] The present invention relates to a xerzole flavonoid derivative, a preparation method, and a use thereof, belonging to organic synthetic chemistry and pesticide technology. Background technique [0002] Flavonoids are a class of plant secondary metabolites, with extensive biological activity, such as herbicide, insecticidal, bactericidal, antioxidant, anti-cancer, anti-inflammatory, anti-vascular disease, antiviral, and other biological activity, many flavonoid compounds Has been applied to the field of medicine and pesticides. In addition, flavonoids are also used as natural dyes, cosmetic addition ingredients, and food additives. [0003] Thiazole contains both heteroatoms, thiazole compounds are important heterocyclic compounds, with bactericidal, insecticidal, herbicidia. Since thiazole and its derivatives have broad-spectrum bactericidal activity, good compatibility and structural easy modification, have been widely used in the field of bactericides. T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D417/14A01N43/78A01P3/00
CPCC07D417/12C07D417/14A01N43/78
Inventor 孟菲严梓鑫杨文超袁树忠董飒冯建国邓维
Owner YANGZHOU UNIV