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Carbazolyl isopropanolamine derivatives with double chiral centers as well as preparation method and application of same

A carbazolyl isopropanolamine and chiral technology, which is applied in the field of carbazolyl isopropanolamine derivatives and their preparation, can solve problems such as harmful effects on ecological environment and plant safety, increasing drug resistance of plant pathogens and the like

Active Publication Date: 2021-04-09
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The long-term use of traditional fungicides, such as thiabylcopper, ecloazole, streptomycin sulfate, etc., not only increases the resistance of plant pathogens, but also has harmful effects on the ecological environment and plant safety.

Method used

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  • Carbazolyl isopropanolamine derivatives with double chiral centers as well as preparation method and application of same
  • Carbazolyl isopropanolamine derivatives with double chiral centers as well as preparation method and application of same
  • Carbazolyl isopropanolamine derivatives with double chiral centers as well as preparation method and application of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1: Preparation of intermediate (R)-9-(oxirane-2-ylmethyl)-9H-carbazole

[0053] Carbazole (6.0mmol), KOH (9.0mmol) and 10mL DMF were added to a 25mL round-bottomed flask, stirred for 30min under ice-bath conditions, then epichlorohydrin (6.0mmol) containing R configuration was added slowly, and The mixture was stirred for 10 minutes. The reaction was terminated after 5 h in ice bath. Extracted with ethyl acetate, washed with saturated ammonium chloride solution, took the organic phase, dried over anhydrous sodium sulfate, desolvated, and column chromatography (PE:EA, V:V=30:1) gave a white solid with a yield of 45.6% . 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), 7.4-7.41 (m, 2H, carbazol-H), 7.26-7.17 (m, 2H, carbazol-H), 4.79 (dd, J=15.7, 3.2Hz, 1H, N- CH 2 ), 4.43 (dd, J=15.7, 5.7Hz, 1H, N- CH 2 ), 3.32 (qd, J=5.8, 3.2Hz, 1H, O- CH 2 ), 2.76 (dd, J=5.0, 4.1Hz, 1H, O-...

Embodiment 2

[0055] Example 2: (R)-1-(9H-carbazol-9-yl)-3-((((R)-1-phenylethyl)amino)propan-2-ol

[0056] (R)-9-(oxirane-2-ylmethyl)-9H-carbazole (0.90mmol), (R)-1-phenylethan-1-amine (1.8mmol) and K 2 CO 3 (0.90mmol) and 5mL of anhydrous isopropanol were dropped into a 15mL reaction flask, then reacted at 60°C for 6 hours, and column chromatography (CH 2 Cl 2 :CH 3 OH (200:1, V / V)), a white solid was obtained with a yield of 79.0%.

[0057] Other target compounds were synthesized by referring to the steps of the above examples using corresponding raw materials or substituents.

[0058] The structure, H NMR spectrum and C NMR spectrum data of the synthesized carbazolyl isopropanolamine derivatives with dual chiral centers are shown in Table 1, and their physicochemical properties are shown in Table 2.

[0059] H NMR spectrum and carbon spectrum data of the compounds in Table 1

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068] ...

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Abstract

The invention relates to carbazolyl isopropanolamine derivatives with double chiral centers as well as a preparation method and application of the same. The compound has a structure as shown in a general formula (I), a series of carbazolyl isopropanolamine derivatives with double chiral centers are synthesized on the basis of carbazole, and the compound has an excellent inhibition effect on plant pathogenic bacteria such as xanthomonas oryzae pv. Oryzae, xanthomonas citri, xanthomonas axonopodis pv. Actinidia and the like.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a carbazolyl isopropanolamine derivative with a double chiral center 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 with high act...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D405/06A01N43/38A01P1/00A01P3/00A01P7/00
CPCC07D209/86C07D405/06A01N43/38C07B2200/07Y02A50/30
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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