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Chiral indolone derivative and synthesis method thereof

A technology of chiral indolinone and synthesis method, which is applied in the field of chiral indolinone derivatives and their synthesis, can solve the problems of limited scope of application of substrates, long synthetic routes, etc., and achieve good application prospects, substrate Wide adaptability and high productivity

Active Publication Date: 2021-08-03
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To sum up, in the existing synthetic methods, there are shortcomings such as the synthetic route is too long, the scope of application of the substrate is limited, etc.

Method used

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  • Chiral indolone derivative and synthesis method thereof
  • Chiral indolone derivative and synthesis method thereof
  • Chiral indolone derivative and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] The synthesis of embodiment 1 compound a

[0097]

[0098] Phenylpropynaldehyde (0.3mmol), p-chloroaniline (0.18mmol), allylpalladium chloride dimer (0.015mmol), (S)-6,6'-bis(triphenylsilyl)spiro Cyclic diphenol phosphate (0.03mmol), Molecular sieves were dissolved in 1.5 mL of anhydrous dichloromethane to prepare mixed solution A; N-methyldiazoacetyl-p-toluidine (0.45 mmol) and β-morpholine styrene (0.36 mmol) were dissolved in 1 mL of anhydrous dichloromethane Prepare mixed solution B; place mixed solution A at 0°C and stir, and add mixed solution B with a syringe pump within 3 hours. After the injection, the reaction system was stirred at 0 °C for 1 h. After the reaction was completed, filter, the filtrate was rotary evaporated to remove the solvent, and then the crude product was purified by column chromatography to obtain pure product a, which was a yellow oily liquid with a yield of 75%, a dr value greater than 20:1, and an ee value of 93%. of the product 1...

Embodiment 2

[0100] The synthesis of embodiment 2 compound b

[0101]

[0102] Phenylpropynaldehyde (0.3mmol), p-chloroaniline (0.18mmol), allylpalladium chloride dimer (0.015mmol), (S)-6,6'-bis(triphenylsilyl)spiro Cyclic diphenol phosphate (0.03mmol), Molecular sieves were dissolved in 1.5 mL of anhydrous dichloromethane to prepare mixed solution A; N-methyldiazoacetyl-p-methoxyaniline (0.45 mmol) and β-morpholine styrene (0.36 mmol) were dissolved in 1 mL of anhydrous Methyl chloride was prepared as mixed solution B; mixed solution A was stirred at 0°C, and mixed solution B was added with a syringe pump within 3 hours. After the injection, the reaction system was stirred at 0 °C for 1 h. After the reaction was completed, filter, the filtrate was rotary evaporated to remove the solvent, and then the crude product was purified by column chromatography to obtain pure product b, which was a yellow oily liquid with a yield of 73%, a dr value greater than 20:1, and an ee value of 90%. ...

Embodiment 3

[0104] The synthesis of embodiment 3 compound c

[0105]

[0106] Phenylpropynaldehyde (0.3mmol), p-chloroaniline (0.18mmol), allylpalladium chloride dimer (0.015mmol), (S)-6,6'-bis(triphenylsilyl)spiro Cyclic diphenol phosphate (0.03mmol), Dissolve molecular sieves in 1.5 mL of anhydrous dichloromethane to prepare mixed solution A; dissolve N-methyldiazoacetanilide (0.45 mmol) and β-morpholine styrene (0.36 mmol) in 1 mL of anhydrous dichloromethane to prepare Mix solution B; place mixed solution A at 0°C and stir, and add mixed solution B with a syringe pump within 3 hours. After the injection, the reaction system was stirred at 0 °C for 1 h. After the reaction was completed, filter, the filtrate was rotary evaporated to remove the solvent, and then the crude product was purified by column chromatography to obtain pure product c, which was a yellow oily liquid with a yield of 67%, a dr value greater than 20:1, and an ee value of 86%. of the product 1 H NMR schematic ...

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Abstract

The invention discloses a synthesis method of a chiral indolone derivative and the chiral indolone derivative synthesized by the synthesis method. According to the synthesis method, diazoamide, aldehyde and enamine are used as raw materials, a water absorbent is added, substituted aniline, a palladium (II) dimer and chiral phosphoric acid form a catalytic system, and the chiral indolone derivative is obtained through a one-pot reaction. The synthesis method has the advantages of simple operation, fast reaction, wide substrate adaptability and the like. The indolone structure prepared by the invention widely exists in natural products, medicines and bioactive molecules, and has a great application prospect.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry. More specifically, it relates to a chiral indolinone derivative and a synthesis method thereof. Background technique [0002] The structure of 2-indolinone widely exists in natural products, drugs and biologically active molecules, and has pharmacological effects such as anti-tumor, anti-inflammatory, growth-promoting, and anti-Parkinson. For example, L-Oxindolylalanine is a metabolite of L-tryptophan, which has good antibacterial activity; FR900452 and Maremycins B are alkaloid compounds produced by marine Streptomyces sp.B9173, which have certain inhibitory effects on lymphoma cells Activity; A.Scala et al. (Bioorg Med Chem.,2014,22(3):1063-9) reported a class of 3-substituted-2-indolone compounds with antiproliferative effects on Leishmania protozoa ; Prioline isolated from sage root can be used to treat tonsillitis, pharyngitis, tuberculosis and bacillary dysentery; a...

Claims

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Application Information

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IPC IPC(8): C07D209/34C07D209/80
CPCC07D209/34C07D209/80C07B2200/07Y02A50/30
Inventor 胡文浩余思凡邱晃华如雨
Owner SUN YAT SEN UNIV
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