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Preparation method for carbazolylv isopropanolamine derivative with chiral center and application

A carbazolyl isopropanolamine, chiral technology, applied in the field of carbazolyl isopropanolamine compounds and their preparation, can solve problems affecting citrus yield, citrus rot, etc.

Active Publication Date: 2019-04-16
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Furthermore, Xanthomonas axonopodis pv. Citri causes citrus rot and affects citrus production globally

Method used

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  • Preparation method for carbazolylv isopropanolamine derivative with chiral center and application
  • Preparation method for carbazolylv isopropanolamine derivative with chiral center and application
  • Preparation method for carbazolylv isopropanolamine derivative with chiral center and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1: Preparation of intermediate (R)-3,6-di-tert-butyl-9-(2-methyloxyethylene)-9H-carbazole

[0058] Put 3,6-di-tert-butylcarbazole (29.9mmol) and potassium hydroxide (35.9mmol) in a 100mL round bottom flask, add 30mL DMF to it and stir, add R-epichlorohydrin (35.9mmol ) after 8 hours of reaction, stop the reaction, extract, and column chromatography (eluent PE:EA=30:1), to obtain a white solid with a yield of 54.5%.

Embodiment 2

[0059] Embodiment 2: Preparation of target compound 1-(9H-carbazolyl-9-yl)-3-((2-chlorobenzyl)amino)-2-hydroxypropanol

[0060] Add 9-(2-methyloxyethylene)-9H-carbazole (0.90mmol) and potassium carbonate (0.90mmol) to 2-chlorobenzylamine (1.80mmol) dissolved in 5mL isopropanol solution, 60°C After reacting for 6 hours, the reaction was stopped, solvent removal, column chromatography (eluent CH 2 Cl 2 :CH 3 OH=200:1) to obtain a white solid with a yield of 74.7%.

[0061] Other compounds were prepared using corresponding starting materials in a similar manner to Example 1 / 2. The structure, H-NMR and C-NMR data of the synthesized carbazolyl isopropanolamine structure compounds are shown in Table 1, and their physical and chemical properties are shown in Table 2.

[0062] H NMR spectrum and carbon spectrum data of some compounds in Table 1

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] Table 2 Physicochemical properties of some t...

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Abstract

The invention relates to a preparation method for a carbazolylv isopropanolamine derivative with the chiral center and application. The structure of the compound is shown in the formula (I), and the compound achieves the better effect of inhibiting xanthomonas oryzae, ralstonia solanacearum, cucumber xanthomonas oryzae, konjak xanthomonas oryzae, xanthomonas citri, grape ulcer bacteria, tomato ulcer bacteria, kiwi fruit ulcer bacteria, apple ulcer bacteria, cucumber botrytis cinerea, chili blight bacteria, sclerotinia sclerotiorum, wheat gibberella saubinetii, potato late blight, blueberry root rotting bacteria and the like.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a carbazolyl isopropanolamine compound with a chiral center and a preparation method and application thereof. Background technique [0002] In recent years, plant bacteria and fungi have seriously affected the yield and quality of crops worldwide, causing huge economic losses to farmers. For example, Xanthomonas oryzaepv. Oryzae, a rod-shaped Gram-negative bacterium that can cause the leaf blight of rice, brings about at least 10-50% yield reduction in rice-growing countries every year. Additionally, Xanthomonas axonopodis pv. Citri causes citrus rot, affecting citrus yields globally. In the process of agricultural production, due to the long-term use of traditional medicaments, plant pathogenic bacteria have developed certain resistance to them. Therefore, it is of great significance to create new high-efficiency, low-toxic and safe green pesticides. [0003] Acco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D209/88C07D405/06C07D401/12A01N43/38A01N43/40A01P1/00A01P3/00
CPCA01N43/38A01N43/40C07D209/86C07D209/88C07D401/12C07D405/06C07B2200/07
Inventor 杨松赵永亮王培义黄星龙青素吴元元薛伟
Owner GUIZHOU UNIV
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