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Isopropanolamine substructure-containing 1, 2, 3, 4-tetrahydro-beta-carboline compound and preparation method and application thereof

A technology of propanolamine sub-compounds, which is applied in the field of medicinal chemistry and can solve problems such as instability to light, complex structure and difficulty in synthesis, and the use of pesticides

Active Publication Date: 2020-07-28
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Natural products not only have a wide variety, diverse biological activities, and unique effects, but more importantly, they are easy to degrade or have good compatibility with the environment, so they have been widely used by people for thousands of years; however, due to the complex structure of most natural product compounds, it is difficult to synthesize. Most are unstable to light or extremely volatile, and usually cannot be directly used as pesticides

Method used

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  • Isopropanolamine substructure-containing 1, 2, 3, 4-tetrahydro-beta-carboline compound and preparation method and application thereof
  • Isopropanolamine substructure-containing 1, 2, 3, 4-tetrahydro-beta-carboline compound and preparation method and application thereof
  • Isopropanolamine substructure-containing 1, 2, 3, 4-tetrahydro-beta-carboline compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: Preparation of intermediate 2-(oxyethylene-2-methylene)-1,2,3,4-tetrahydro-β-carboline

[0046] 1,2,3,4-tetrahydro-β-carboline (5.0g, 28.45mmol), K 2 CO 3 (0.95g, 34.14mmol) and 30mL DMF were added to a 100mL round-bottomed flask, stirred in an ice bath for 10min, then epibromopropane (1.05g, 37.05mmol) was slowly added, and reacted at room temperature for 24h to end the reaction. The reaction was quenched with water, extracted with ethyl acetate, washed with saturated ammonium chloride solution, the organic phase was taken, dried over anhydrous sodium sulfate, precipitated, and column chromatographed to obtain a white solid with a yield of 37.9%. Its NMR data are: 1 H NMR (500MHz, CDCl 3 )δ7.98(s, 1H, -NH), 7.46(d, J=7.7Hz, 1H, Ar-H), 7.26(d, J=7.9Hz, 1H, Ar-H), 7.12(dt, J =7.1, 1.3Hz, 1H, Ar-H), 7.07(dt, J=7.8, 1.1Hz, 1H, Ar-H), 3.88-3.82(m, 1H, -N-CH 2 -), 3.66 (dt, J=14.7, 1.5Hz, 1H, -N-CH 2 -), 3.24-3.17(m, 1H, -O-CH-), 3.05(dd, J=13.4, 2.9Hz, 1...

Embodiment 2

[0048] Example 2: 1-(piperidin-1-yl)-3-(1,2,3,4-tetrahydro-β-carbolin-2-yl)-propan-2-ol

[0049] Put 2-(oxyethylene-2-methylene)-1,2,3,4-tetrahydro-β-carboline (0.23g, 1.0mmol), benzylamine (2.0mmol) and 5mL absolute ethanol into 15mL reaction bottle, then reacted at 60°C, followed by TLC until 2-(oxyethylene-2-methylene)-1,2,3,4-tetrahydro-β-carboline was completely consumed, and the reaction was terminated. The reaction was quenched by adding 20 mL of water, and extracted twice with 30 mL of dichloromethane, the organic phase was collected, dried over anhydrous sodium sulfate, precipitated, and column chromatographed to obtain a white solid with a yield of 91.9%.

Embodiment 3

[0050] Example 3: 1-(benzylamino)-3-(1,2,3,4-tetrahydro-β-carbolin-2-yl)propan-2-ol converts 2-(oxyethylene-2-methylene Base)-1,2,3,4-tetrahydro-β-carboline (0.23g, 1.0mmol), potassium carbonate (0.3mmol), piperidine (1.1mmol) and 6mL isopropanol were put into 15mL in one pot Then react at room temperature, TLC tracking, until 2-(oxyethylene-2-methylene)-1,2,3,4-tetrahydro-β-carboline is completely consumed, the reaction is terminated. The reaction was quenched by adding 20 mL of water, and extracted twice with 30 mL of dichloromethane, the organic phase was collected, dried over anhydrous sodium sulfate, precipitated, and column chromatographed to obtain a white solid with a yield of 95.7%.

[0051] The following compounds were prepared by the steps similar to the above examples, only replacing the corresponding raw materials. The structure and H-NMR and C-NMR data of the compound are shown in Table 1, and their physicochemical properties are shown in Table 2.

[0052] H NM...

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Abstract

The invention relates to an isopropanolamine substructure-containing 1, 2, 3, 4-tetrahydro-beta-carboline compound and a preparation method and application thereof. The compound has a structure as shown in a general formula (I), based on 1, 2, 3, 4-tetrahydro-beta-carboline, a nitrogen-containing fragment is introduced into the system, a series of 1, 2, 3, 4-tetrahydro-beta-carboline compounds containing isopropanolamine substructures are synthesized, and the compounds have an excellent inhibition effect on plant pathogenic bacteria such as xanthomonas oryzae pv. oryzae, xanthomonas citri, actinidia canker and the like.

Description

technical field [0001] The application relates to the technical field of medicinal chemistry, in particular to a 1,2,3,4-tetrahydro-β-carboline compound containing an isopropanolamine substructure and its preparation method and application. 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A01N43/90A01P3/00A01P1/00
CPCC07D471/04A01N43/90Y02A50/30
Inventor 王培义杨松刘洪武吉庆田宿芬王方吴志兵
Owner GUIZHOU UNIV
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