Method for rapidly preparing abscisic acid receptor stimulant

An abscisic acid receptor and agonist technology, applied in the field of chemical synthesis and plant growth regulation, can solve the problems of restricting promotion speed, low efficiency, and many steps, and achieve high application value, enhanced tolerance, and extensive sources Effect

Inactive Publication Date: 2019-04-26
SHAOYANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the existing preparation method, there are many steps, the efficiency is not high, and the chemical property of the intermediate 4-methylbenzylsulfonyl chloride is unstable, which restricts its popularization speed

Method used

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  • Method for rapidly preparing abscisic acid receptor stimulant
  • Method for rapidly preparing abscisic acid receptor stimulant
  • Method for rapidly preparing abscisic acid receptor stimulant

Examples

Experimental program
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Effect test

specific Embodiment 1

[0027] Two-step one-pot method for preparing an abscisic acid receptor agonist: add p-methylbenzyl mercaptan to acetonitrile, then add a chlorinating reagent, spot the plate for monitoring, move it into an ice-water bath after the reaction, and add 4 equivalents of an acid-binding agent Such as pyridine, slowly drop 7-amino- N -Acetonitrile solution of propyl quinolinone, spot plate to monitor the reaction, after the reaction, pickling, drying, and further column chromatography or recrystallization can obtain the abscisic acid receptor agonist, its NMR data is as follows 1 H NMR (600 MHz, DMSO- d 6 ): δ9.66 (s, 1H), 7.16 (s, 4H), 7.11-7.03 (m, 2H), 6.99 (s, 1H), 4.37 (s, 2H),3.86-3.72 (m, 2H), 2.89-2.72 (m, 2H), 2.52 (s, 2H), 2.29 (s, 3H), 1.53 (m, 2H), 0.87 (t, J = 7.2 Hz, 3H). The reaction equation is:

[0028]

specific Embodiment 2

[0029] Two-step one-pot method: add p-bromobenzylmercaptan to acetonitrile, then add chlorinated reagent, spot plate monitoring, after the reaction is completed, move it into an ice-water bath, add 4 equivalents of an acid-binding agent such as pyridine, and slowly drop it after the addition 7-amino- N -Acetonitrile solution of propyl quinolinone, spot plate to monitor the reaction, after the reaction, pickling, drying, and further column chromatography or recrystallization can obtain the abscisic acid receptor agonist, its NMR data is as follows 1 H NMR (600 MHz, DMSO- d 6 ): δ 9.67 (s, 1H), 7.18 (s,4H), 7.12-7.03 (m, 2H), 7.00 (s, 1H), 4.36 (s, 2H), 3.85-3.70 (m, 2H), 2.88 -2.71 (m, 2H), 2.30 (s, 3H), 1.52 (m, 2H), 0.88 (t, J = 7.2 Hz, 3H). The reaction equation is:

[0030]

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Abstract

The invention discloses a method for rapidly preparing an abscisic acid receptor stimulant and relates to a chemical synthesis and plant growing regulation technology. The method is characterized in that the two-step one-pot strategy is adopted, 4-methylbenzyl mercaptan serves as a raw material, in-situ generated 4-methylbenzylsulfonyl chloride and prepared 7-amino-N-propylquinolinone react, and thus the abscisic acid receptor stimulant can be obtained. The strategy is wild in reaction condition, short in step and high in yield, the raw material is cheap and easy to obtain, and the strategy can be used for rapidly preparing the formula (I) and a derivative or analogue thereof. The method for rapidly preparing the abscisic acid receptor stimulant is low in cost and easy to operate and has high application value.

Description

technical field [0001] The invention relates to chemical synthesis and plant growth regulation technology; more specifically, the invention relates to a method for rapidly preparing an abscisic acid receptor agonist. Background technique [0002] Recent studies have found that the anti-stress hormone abscisic acid enhances stress tolerance by regulating the antioxidant-reductase system in plants and accumulating osmotic adjustment substances such as proline and soluble sugars. However, abscisic acid is photosensitive, easily inactivated by metabolism, difficult to chemically synthesize, and high in cost, which limit its application in production and daily life. By studying the binding mechanism of receptor proteins and small molecules, with the help of computer assistance, a kind of abscisic acid receptor agonist AM1 was finally discovered, which has high biological activity and stable chemical properties, showing great market application and promotion value. However, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/38
CPCC07D215/38
Inventor 黄志友
Owner SHAOYANG UNIV
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