Carbazole isopropanol diamine compound containing 1, 2, 3-triazole as well as preparation method and application of carbazole isopropanol diamine compound

A carbazole isopropanol and compound technology, which is applied in the field of medicinal chemistry and can solve problems such as harmful effects on ecological environment and plant safety, and increasing drug resistance of plant pathogens.

Pending Publication Date: 2021-04-02
GUIZHOU UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

The long-term use of traditional fungicides, such as thiabylcopper, ecloazole, streptomycin sulfate, etc., not only...

Method used

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  • Carbazole isopropanol diamine compound containing 1, 2, 3-triazole as well as preparation method and application of carbazole isopropanol diamine compound
  • Carbazole isopropanol diamine compound containing 1, 2, 3-triazole as well as preparation method and application of carbazole isopropanol diamine compound
  • Carbazole isopropanol diamine compound containing 1, 2, 3-triazole as well as preparation method and application of carbazole isopropanol diamine compound

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Embodiment 1: the preparation of intermediate 9-(2,3-epoxypropyl)-9H-carbazole

[0049] Carbazole (6.0mmol), KOH (0.90mmol) and 10mL DMF were added to a 100mL round-bottomed flask, stirred for 30 minutes under ice-bath conditions, then epoxybromopropane (6.0mmol) was slowly added dropwise in the system, and ice After bath reaction for 5h, end the reaction; use ethyl acetate (50mL) to extract, then use saturated NH 4 Cl aqueous solution (3×20mL), washed with anhydrous Na 2 SO 4 Drying, precipitation, and column chromatography (PE:EA=30:1, V / V) gave a white solid with a yield of 76.9%. Its NMR data are: 1 H NMR (400MHz, DMSO-d 6 , ppm) δ8.15 (d, J=7.7Hz, 2H, carbazol-H), 7.66 (d, J=8.3Hz, 2H, carbazol-H), 7.49-7.40 (m, 2H, carbazol-H), 7.22 (t, J = 7.4Hz, 2H, carbazol-H), 4.79 (dd, J = 15.7, 3.2Hz, 1H), 4.43 (dd, J = 15.7, 5.6Hz, 1H), 3.31 (dt, J = 6.8, 2.9Hz, 1H), 2.79-2.73(m, 1H), 2.58(dd, J=5.1, 2.6Hz, 1H); 13 C NMR (101MHz, DMSO-d 6 , ppm) δ140.3, 125.7, 122.1...

Embodiment 2

[0050] Embodiment 2: Preparation of intermediate 1-(9H-carbazol-9-yl)-3-(propargylamino)-2-propanol

[0051] 9-(2,3-epoxypropyl)-9H-carbazole (0.90mmol), K 2 CO 3 (0.90mmol) and 5mL of anhydrous isopropanol were added into a 25mL round bottom flask, then propargylamine (1.8mmol) was added, and reacted at 60°C, and the reaction was terminated after 6h. Desolvation, column chromatography (CH 2 Cl 2 :CH 3 OH=200:1, V / V), a white solid was obtained with a yield of 41.2%. Its NMR data are: 1 H NMR (400MHz, DMSO-d 6 , ppm) δ8.13 (d, J=7.6Hz, 2H, carbazol-H), 7.62 (d, J=8.3Hz, 2H, carbazol-H), 7.43 (t, J=7.7Hz, 2H, carbazol-H) H), 7.19 (t, J=7.4Hz, 2H, carbazol-H), 5.75 (s, 1H, NH), 5.04 (d, J=5.2Hz, 1H, OH), 4.46 (dd, J=14.7, 4.8Hz, 1H, N- CH 2 ), 4.28 (dd, J=14.7, 7.1Hz, 1H, N- CH 2 ), 4.11-3.88(m, 1H, CH), 3.36(t, J=2.2Hz, 2H, NH- CH 2 ), 3.05(t, J=2.4Hz, 1H, C·CH), 2.70-2.56(m, 2H, CH- CH 2 ); 13 C NMR (101MHz, DMSO-d 6 , ppm) δ141.1, 126.0, 122.5, 120.5, 11...

Embodiment 3

[0053] Example 3: Target compound 16 (1-(9H-carbazol-9-yl)-3-(((1-(4-fluorophenyl)-1H-1,2,3-triazole-4- base) methylene) amino) -2-propanol) preparation

[0054] 1-(9H-carbazol-9-yl)-3-(propargylamino)-2-propanol (1.08 mmol) and p-fluorophenyl azide (4.32 mmol) were dissolved in 5 mL DCM and charged to 15 mL reaction In the bottle, NaASC (0.22mmol) and CuSO 4 ·5H 2 O (0.11 mmol) was dissolved in water (0.5 mL), added to the reaction system, and stirred overnight at room temperature. TLC tracking, after the reaction is complete, add water to quench the reaction, then use CH 2 Cl 2 (50mL) extraction, take the organic phase, through anhydrous Na 2 SO 4 After drying, desolvation, and then column chromatography (CH 2 Cl 2 :CH 3 OH=200:1, V / V), a yellow solid was obtained with a yield of 48.1%. Its NMR data are: 1 H NMR (400MHz, DMSO-d 6 , ppm) δ8.63 (s, 1H, triazole-H), 8.12 (d, J=7.5Hz, 2H, carbazol-H), 7.98-7.83 (m, 2H, benzyl-H), 7.63 (d, J =8.3Hz, 2H, carbazol-H), ...

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Abstract

The invention relates to a carbazole isopropanol diamine compound containing 1, 2, 3-triazole as well as a preparation method and application of the carbazole isopropanol diamine compound. The compound has a structure as shown in a general formula (I) which is described in the specification. Carbazole is used as a basis, and a nitrogen-containing fragment is introduced into the system to synthesize a series of isopropanolamine-containing substructures and 1, 2, 3-triazole carbazole compounds; the compound has an excellent inhibition effect on plant pathogenic bacteria such as xanthomonas oryzae pv. Oryzae, xanthomonas axonopodis pv. Citri and Pseudomonas syringae pv.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a 1,2,3-triazolecarbazole compound containing an isopropanolamine substructure and a preparation method and application thereof. Background technique [0002] Plant bacterial diseases are one of the main factors affecting global agricultural production, seriously affecting the yield and quality of agricultural products, not only causing great economic losses, but also threatening human health. For example, rice bacterial blight, citrus canker, kiwifruit canker, tobacco bacterial wilt, etc., break out to varying degrees every year, causing huge economic losses to farmers. The long-term use of traditional fungicides, such as thiabylcopper, eucumazole, and streptomycin sulfate, not only increases the resistance of plant pathogens, but also has harmful effects on the ecological environment and plant safety. Therefore, there is an urgent need to develop new pesticides wit...

Claims

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Application Information

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IPC IPC(8): C07D403/12C07D401/14A01N43/647A01P1/00A01P3/00
CPCC07D403/12C07D401/14A01N43/647
Inventor 王培义黄星刘洪武龙周卿张玲朱建军杨松柳立伟
Owner GUIZHOU UNIV
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