Quinoline amide compounds and preparation method and application thereof

A compound, quinoline technology, which is applied in the field of quinoline amide compounds and their preparation, can solve the problems of brassinolide synthesis cost, easy metabolism inactivation, and many metabolic sites, so as to improve lodging resistance, The effect of easy preparation and low cost

Active Publication Date: 2017-06-09
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no solution to the problems of high synthesis cost of brassinosteroids, many metabolic sites in the body, and easy metabolic inactivation. Therefore, the search for new target receptors for the development of analogues has attracted increasing attention.
[0003] US6667278 (2003) re...

Method used

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  • Quinoline amide compounds and preparation method and application thereof
  • Quinoline amide compounds and preparation method and application thereof
  • Quinoline amide compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1, the preparation of compound 1a:

[0057]

[0058] In a 100mL round-bottomed flask, add 8-aminoquinoline (10mmol) and succinic anhydride (12mmol), stir and dissolve 15mL tetrahydrofuran (solvent A), heat up and reflux for 2 hours for acylation reaction, cool down and cool down to precipitate a solid, filter A solid was obtained and purified by recrystallization from ethanol. The specific method of recrystallization is: add 3 mL of ethanol dropwise to 1 g of the primary product to be recrystallized, heat to reflux until the primary product is completely dissolved, and continue to reflux for 10 minutes, then slowly cool down to precipitate a solid, and filter with suction to obtain a pure product.

Embodiment 2

[0059] Embodiment 2, the preparation of compound 1b:

[0060]

[0061] In a 100mL round-bottomed flask, add 8-aminoquinoline (10mmol), succinic anhydride (12mmol), 15mL tetrahydrofuran and stir to dissolve, reflux for 3 hours for acylation reaction, cool down to precipitate a solid, filter to obtain a solid, and recrystallize from ethanol The intermediate product was purified. Take the intermediate product (10mmol), dissolve it in 3ml of methanol, cool it to 0°C in an ice-salt bath, add 5ml of THF solution that has been prepared to obtain thionyl chloride dropwise at a constant temperature, and complete the dropwise addition in 30 minutes; continue to react for 5 hours, and pour the reaction mixture into 150mL In ice water, extracted with ethyl acetate (3x100mL), washed with saturated brine (3x100mL), anhydrous Na 2 SO 4 After drying, concentration by filtration, the crude product was purified by recrystallization from ethanol or ethyl acetate. The specific method of rec...

Embodiment 3

[0062] Embodiment 3, the preparation of compound 1d:

[0063] Compound 1d was prepared as follows:

[0064]

[0065] In a 100mL round bottom flask, add 8-aminoquinoline (10mmol), 3mL (20mmol) triethylamine, 15ml tetrahydrofuran and stir to dissolve, then add TBTU (3.531g, 11mmol) and Boc-amino acid (10mmol). The reaction mixture was stirred at room temperature for acylation reaction for 12 h, and the progress of the reaction was detected by TLC. After the reaction, concentrate and dissolve with dichloromethane (50mL), adjust pH to 10 with 1M NaOH, after the system is separated, take the aqueous phase, acidify to pH=3 with 1M HCl, extract with ethyl acetate (3×100mL), wash with saturated brine ( 3x100mL), anhydrous Na 2 SO 4 After drying, concentration by filtration, the crude product was purified by recrystallization from ethanol. The specific method of recrystallization is: add 3 mL of ethanol dropwise to 1 g of the primary product to be recrystallized, heat to reflux ...

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Abstract

The invention discloses quinoline amide compounds and a preparation method and application thereof. A structural formula of the quinoline amide compounds is shown as a formula I. According to biological activity verification, specific brassinolide reactions such as promotion of arabidopsis mutant det2-1 hypocotyl elongation in the dark and rice blade tilt angle increase, improvement of corn salt stress resistance and the like of some of the compounds are discovered; several compounds have high response values under the condition low concentration and are capable of inhibiting wheat plant height to retard growth and improve lodging resistance under the condition of high concentration; in addition, excellent effects in prevention and control of gramineous weeds such as wild oats, aegilops tauschii, barnyard grass, setaria viridis and aegilops. The quinoline amide compounds are easy to prepare, low in cost, high in agricultural application and promotion value and worthy of subsequent intensive research and development.

Description

technical field [0001] The invention belongs to the field of plant growth regulators, and relates to a quinoline amide compound and a preparation method and application thereof. Background technique [0002] Brassinolides, also known as brassinolides (BRs), are a class of endogenous plant growth regulators synthesized in plants. It can regulate a variety of enzymes and hormones needed by plants, give full play to the potential and growth advantages of plants, and enhance vitality and drought and waterlogging resistance. In view of the extremely low content of brassinolide etc. in plants (less than 10 -6 ppm) and its excellent physiological activity as a plant hormone in agricultural crops, its synthesis and transformation research has always been favored by scientists from all over the world. However, there is no solution to the problems of high synthesis cost of brassinosteroids, many metabolic sites in the body, and easy metabolic inactivation. Therefore, the exploration...

Claims

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Application Information

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IPC IPC(8): C07D215/40A01N43/42A01P21/00A01P13/00
Inventor 段留生刘少金于春欣胡堂路于莎周于毅李召虎
Owner CHINA AGRI UNIV
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