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Photostable cis 2, 3-cyclopropanated abscisic acid analogue and preparation method thereof

A technology of cyclopropanation and abscisic acid, which is applied to the preparation of oxygenated compounds, botany equipment and methods, chemical instruments and methods, etc., can solve the problems of poor biological activity and loss of meaning

Inactive Publication Date: 2013-02-06
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome this defect, a series of abscisic acid analogs with good photostability have been designed and synthesized, but unfortunately they are meaningless because of their poor biological activity, so this problem has not been solved so far.

Method used

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  • Photostable cis 2, 3-cyclopropanated abscisic acid analogue and preparation method thereof
  • Photostable cis 2, 3-cyclopropanated abscisic acid analogue and preparation method thereof
  • Photostable cis 2, 3-cyclopropanated abscisic acid analogue and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Embodiment 1: the synthesis of compound (III)

[0013] The first step: the synthesis of ethyl (Z)-5-trimethylpent-2-en-4-ynoate (IV)

[0014] In a 250 mL dry three-necked flask, 7.84 g of ethyl propiolate, 10.06 g of anhydrous lithium bromide, 5.28 g of acetic acid and 80 mL of anhydrous acetonitrile were sequentially added, stirred, and heated to reflux for 22 h. Then cool to room temperature, pass through nitrogen protection, first add solvent anhydrous triethylamine 120mL under stirring, then add trimethylsilylacetylene 10.43g, bistriphenylphosphorous palladium chloride 0.99g and cuprous iodide 0.54 g. The reaction was carried out under ice bath for 6 h. After the reaction was completed, the reaction solution was passed through a small section of silica gel decompression column, and the column was washed with ethyl acetate. The obtained filtrate was concentrated to obtain a brown liquid. Direct column chromatography (petroleum ether: ethyl acetate = 8:1) gave 12.7 ...

Embodiment 2

[0032] Example 2: Photostability of Cis-2,3-cyclopropanated abscisic acid analog (III)

[0033] Using a 254nm ultraviolet lamp as the light source (the light source comes from the ZF-I three-purpose ultraviolet analyzer), keep the relative position (5cm) of the sample bottle and the ultraviolet lamp constant during illumination. The structure of the isomerization product was confirmed by HPLC-MS, the photoisomerization of different conditions and compounds was evaluated by HPLC, and the analysis method of each compound was established. The area normalization method was used to determine the photoisomerization content of each compound.

[0034] Drug preparation: accurately weigh 2.6mg (1.0×10 -5 mol) compound (III), dissolved in 1 mL of methanol to obtain a 10 mmol / L stock solution of each compound, and stored at -20°C in the dark. Pipette 100 μL stock solution and dilute to 10 mL with water for light experiment. Keep the relative position (5cm) between the sample bottle and...

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Abstract

An abscisic acid (1) is a plant hormone widely existing in a plant and has important physiological function, however, the application range is limited by the high-speed photo-isomerization characteristics. A bioisosteres cis 2, 3-cyclopropanated abscisic acid analogue of the abscisic acid is compounded through 2, 3-cyclopropanation, and the photostability is four times as that of the abscisic acid.

Description

technical field [0001] The invention relates to a synthesis method and application of a class of cis-2,3-cyclopropanated abscisic acid analogs with better photostability. Background technique [0002] Abscisic acid (I) is a phytohormone widely present in plants. It was first isolated from cotton bolls by Ohkuma in 1963. It forms with plant abscission, induces dormancy, inhibits germination, promotes organ aging and shedding, and enhances stress resistance Sex and so on are closely related, known as "plant stress resistance factor". [0003] However, a major defect of abscisic acid in practical use is that under light conditions, the 2-cis-diene structure of ABA is very easy to isomerize into trans-abscisic acid (II), which is basically inactive. [0004] [0005] In order to overcome this defect, a series of abscisic acid analogues with good photostability have been designed and synthesized, but unfortunately they are meaningless because of their poor biological activity...

Claims

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Application Information

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IPC IPC(8): C07C62/38C07C27/02A01N37/42A01P21/00
Inventor 覃兆海肖玉梅刘文剑范锦龙韩小强
Owner CHINA AGRI UNIV
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