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Method for constructing On-DNA alpha-amino amide compound through aqueous-phase Ugi multi-component reaction

A multi-component reaction and aminoamide technology, applied in the field of coding compound libraries, can solve problems such as low efficiency and inconvenient operation

Inactive Publication Date: 2021-05-28
HITGEN INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The former method usually requires multi-step continuous synthesis, and the efficiency is low, while the latter method needs to immobilize DNA into special materials, which is inconvenient to operate

Method used

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  • Method for constructing On-DNA alpha-amino amide compound through aqueous-phase Ugi multi-component reaction
  • Method for constructing On-DNA alpha-amino amide compound through aqueous-phase Ugi multi-component reaction
  • Method for constructing On-DNA alpha-amino amide compound through aqueous-phase Ugi multi-component reaction

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0142] The synthesis of embodiment 1, compound 1

[0143]

[0144] Propylamine (6.67μL, 333 molar equivalents, 1M MeOH solution) and DNA-CHO (20μL, 20nmol, 1mM aqueous solution) were pre-mixed evenly, and the reaction solution was activated at room temperature for 2 hours. After activation, add Acetic acid (6.67 μL, 333 molar equivalents, 1M MeOH solution), then add tert-butylisonitrile (6.67 μL, 333 molar equivalents, 1M MeOH solution), mix the reaction solution thoroughly, and then place the reaction solution at 60°C The next 16 hours.

[0145] After the reaction is completed: ethanol precipitation, add 4 μL, 5M sodium chloride solution to the solution, and then continue to add 120 μL absolute ethanol, after shaking evenly, freeze the reaction at -20°C for 2 hours, and then centrifuge at high speed After half an hour, the supernatant was discarded, and the remaining precipitate was dissolved in deionized water to obtain compound 1 with a conversion rate of 15%.

Embodiment 2

[0146] The synthesis of embodiment 2, compound 2

[0147]

[0148] Cyclohexylamine (6.67 μL, 333 molar equivalents, 1M MeOH solution) and DNA-CHO (20 μL, 20 nmol, 1 mM aqueous solution) were pre-mixed uniformly, and the reaction solution was activated at room temperature for 2 hours. After activation, First add acetic acid (6.67 μL, 333 molar equivalents, 1M MeOH solution), then add tert-butylisonitrile (6.67 μL, 333 molar equivalents, 1M MeOH solution), mix the reaction solution thoroughly, and then place the reaction solution at 60 16 hours under the condition of ℃.

[0149] After the reaction is completed: ethanol precipitation, add 4 μL, 5M sodium chloride solution to the solution, and then continue to add 120 μL absolute ethanol, after shaking evenly, freeze the reaction at -20°C for 2 hours, and then centrifuge at high speed After half an hour, the supernatant was discarded, and the remaining precipitate was dissolved in deionized water to obtain compound 2 with a co...

Embodiment 3

[0150] The synthesis of embodiment 3, compound 3

[0151]

[0152] Mix aniline (6.67μL, 333 molar equivalents, 1M MeOH solution) and DNA-CHO (20μL, 20nmol, 1mM aqueous solution) in advance, and activate the reaction solution at room temperature for 2 hours. After activation, add Acetic acid (6.67 μL, 333 molar equivalents, 1M MeOH solution), then add tert-butylisonitrile (6.67 μL, 333 molar equivalents, 1M MeOH solution), mix the reaction solution thoroughly, and then place the reaction solution at 60°C The next 16 hours.

[0153] After the reaction is completed: ethanol precipitation, add 4 μL, 5M sodium chloride solution to the solution, and then continue to add 120 μL absolute ethanol, after shaking evenly, freeze the reaction at -20°C for 2 hours, and then centrifuge at high speed After half an hour, the supernatant was discarded, and the remaining precipitate was dissolved in deionized water to obtain compound 3 with a conversion rate of 51%.

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Abstract

The invention relates to a method for constructing On-DNA alpha-amino amide compounds through aqueous-phase Ugi multi-component reaction, which is characterized in that amine, carboxylic acid, isocyanide and aldehyde are used as raw materials, and alpha-amino amide compounds with different structures are synthesized through Ugi reaction. The method can efficiently and quickly construct peptides, peptidomimetic compounds and various heterocyclic structure compounds, and is suitable for synthesizing a DNA coding compound library by using a porous plate.

Description

technical field [0001] The invention belongs to the technical field of encoded compound libraries, and in particular relates to a method for constructing On-DNA α-aminoamide compounds by aqueous phase Ugi multi-component reaction in the construction of DNA encoded compound libraries. Background technique [0002] In drug development, especially new drug development, high-throughput screening for biological targets is one of the main means to quickly obtain lead compounds. However, the traditional high-throughput screening based on a single molecule requires a long time, huge investment in equipment, limited number of library compounds (millions), and the construction of a compound library requires decades of accumulation, which limits the efficiency and efficiency of lead compound discovery. possibility. The DNA-encoded compound library technology (WO2005058479, WO2018166532, CN103882532) that has emerged in recent years combines combinatorial chemistry and molecular biolog...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/00C07H21/04C40B40/06C40B50/08
CPCC07H1/00C07H21/04C40B40/06C40B50/08
Inventor 李进纪跃罗华东戴东良沈思敏刘观赛万金桥
Owner HITGEN INC
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