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Imidazopyrazinone compound as well as preparation method and application thereof

A technology of imidazo and compound, which is applied in the field of imidazopyrazinone compounds and their preparation, can solve the problems of fast decay speed, low bioluminescence intensity, and Millet's constant, and achieve the effect of increasing half-life

Active Publication Date: 2021-10-08
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Thereby this kind of compound solves the problems such as low bioluminescence intensity, short duration, fast decay speed of NanoLuc-Furimazine bioluminescent system well, and the inventor also finds that this kind of compound also has smaller Michaelis constant, and with NanoLuc Better Affinity

Method used

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  • Imidazopyrazinone compound as well as preparation method and application thereof
  • Imidazopyrazinone compound as well as preparation method and application thereof
  • Imidazopyrazinone compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1 : 2-(furan-2-ylmethyl)-6-phenyl-8-((1-deuterium-1-phenyl)methyl)imidazo[1,2-a]pyrazine-3(7H) - Preparation of ketone (F2)

[0075] Preparation of 1-deuterium-1-phenylcarbinol (2) (phenylmethan-d-ol):

[0076] Deuterated lithium aluminum hydride (160mg, 3.82mmol) was added to a 25mL double-neck flask, under nitrogen protection, 5mL of ultra-dry tetrahydrofuran was added, in an ice bath, at 0°C, using a syringe to drop Benzaldehyde (540mg, 5.10mmol) in ultra-dry tetrahydrofuran, reacted at 0°C for 30min, monitored by TLC, added 160μL of water, 160μL of 15% sodium hydroxide, and 480μL of water, continued to stir for 5min, and filtered through diatomaceous earth , diatomite was washed with diethyl ether, the filtrate was collected, washed with saturated brine to obtain the organic phase compound, dried over anhydrous sodium sulfate, mixed with 100-200 mesh silica gel, packed into a column with 200-300 mesh silica gel, and prepared with a certain proportion of p...

Embodiment 2

[0097] Example 2 : 2-(furan-2-ylmethyl)-6-phenyl-8-((1,1-dideutero-1-phenyl)methyl)imidazo[1,2-a]pyrazine-3 Preparation of (7H)-ketone

[0098] 1,1-Dideuterium-1-phenylmethanol (4) (phenylmethan-d 2 -ol) preparation:

[0099] Deuterated lithium aluminum hydride (201mg, 4.79mmol) was added to a 25mL double-neck flask, and under nitrogen protection, 5mL of ultra-dry tetrahydrofuran was added, and in an ice bath, at 0°C, using a syringe, dropwise added Ethyl benzoate (600mg, 4.00mmol), react at room temperature for 1h, monitor the reaction by TLC, cool the reaction solution to 0°C, add 0.5mL of heavy water, and continue stirring for 30min at 0°C, using diatom Filter with soil, wash with ether, dry with anhydrous sodium sulfate, spin dry, mix the sample with 100-200 mesh silica gel, pack with 200-300 mesh silica gel, and use a certain proportion of ethyl acetate and petroleum ether for gradient elution to obtain Intermediate compound 4, 380mg of colorless transparent oily com...

Embodiment 3

[0114] Example 3 : 2-(furan-2-ylmethyl)-6-phenyl-8-((1,1-dideuterio-1-(2,3,4,5,6-pentadeuteriophenyl))methanol base) imidazo[1,2-a]pyrazin-3(2H)-one

[0115] 1,1-Dideuterium-1-(2,3,4,5,6-pentadeuteriophenyl)-1-bromomethane (1)(1-(bromomethyl-d 2 )benzene-2,3,4,5,6-d 5 ) preparation:

[0116] Deuterated toluene (1g, 9.98mmol, toluene-d 8 ) and N-bromosuccinimide (1.78g, 9.98mmol) were dissolved in 50mL of carbon tetrachloride, and then tert-butyl peroxybenzoate (581mg, 2.99mmol) was added. React at 90°C for 2 hours, use TLC to monitor the reaction, the reaction is complete, stop the reaction, filter, remove the succinimide in the reaction solution, collect the filtrate, spin dry, add 100-200 mesh silica gel to mix the sample, and mix with 200 -300 mesh silica gel column, with petroleum ether as eluent, to obtain intermediate compound 1, R f About 0.5, developer: petroleum ether, 1.1 g of colorless oily compound, yield 62%. 13 C NMR(101MHz,DMSO)δ138.22,129.56,129.32,129....

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Abstract

The invention provides an imidazopyrazinone compound as well as a preparation method and application thereof. The structure of the imidazo pyrazinone compound is shown as a formula I which is described in the specification. In the formula I, R1 is a phenyl group, and R2 is a benzyl group. The compound has at least one D substituent, and the D substituent is located on R1 and / or R2. The compound has excellent luminescence performance, can be used as a substrate of a NanoLuc luminescence system, and is applied to detection of luciferase and detection of drugs.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to an imidazopyrazinone compound and its preparation method and application. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Deuterium is a stable isotope of hydrogen. Deuterium is a method of replacing hydrogen atoms at specific positions in the molecular structure of compounds with deuterium atoms. The main purpose of this type of compound modification is to change the activity of the original compound while maintaining the activity of the original compound. Its metabolic speed, slow down the metabolic rate and so on. Currently, deuterons are essential tools in the fields of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06G01N21/64A61K49/00
CPCC07D487/04C09K11/06G01N21/6428A61K49/0019C07B2200/05C09K2211/1059C09K2211/1088Y02P20/55
Inventor 李敏勇杜吕佩杨月利
Owner SHANDONG UNIV
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