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Melatonin derivative and preparation method and application thereof

A technology of melatonin and derivatives, applied in the field of melatonin derivatives and its preparation, can solve the problems of limiting research progress, short residence time, low solubility, etc., achieve broad application prospects, prolong residence time, and increase curative effect Effect

Active Publication Date: 2019-04-16
李昱飞 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, melatonin has attracted more and more attention from researchers, but due to the characteristics of its molecule itself, its solubility in water is extremely low, and the poor water solubility greatly limits the medicinal efficacy of melatonin.
Due to the low water solubility of melatonin, it cannot be well dissolved in water when preparing medicines and plant growth regulators, but can only be dissolved in organic solvents, which increase the toxic and side effects of melatonin
On the other hand, due to the low water solubility and high fat solubility of melatonin, it quickly penetrates the blood-brain barrier and stays in the blood in the brain for a short time, which affects its curative effect.
Researchers also need to dissolve melatonin in water when studying the mechanism of action of melatonin on animals and humans. Due to its low water solubility, its research progress is limited.

Method used

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  • Melatonin derivative and preparation method and application thereof
  • Melatonin derivative and preparation method and application thereof
  • Melatonin derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 100 mg of natural melatonin (Mel) was dissolved in 10 mL of THF (tetrahydrofuran), and then 69 mg of NaH was added on an ice bath. Reacted for 30 minutes while stirring on an ice bath; 88 mg of 1-4 butane sultone was added to the above reaction solution, then the reaction was returned to room temperature, and continued to stir overnight; the reaction was completed by TLC (thin layer chromatography) point plate analysis , add ice water 30mL to the reaction solution to quench the reaction; extract the reaction solution with ethyl acetate, take the water phase, and use a rotary evaporator to remove moisture under reduced pressure; the residue obtained after rotary evaporation is separated and purified by column chromatography to obtain 100mg The target molecular product, Mels, is a light yellow solid, and its hydrogen spectrum, carbon spectrum, and mass spectrum are as follows: Figure 1 to Figure 3 shown. Its synthetic reaction formula is as follows:

[0038]

[0039...

Embodiment 2

[0044]100 mg of melatonin was dissolved in 10 mL of THF (tetrahydrofuran), and then NaH (69 mg) was added on an ice bath. The reaction was stirred for 30 min on an ice bath. 1-3 propane sultone (79 mg) was added to the above reaction solution, then the reaction was returned to room temperature and stirring was continued overnight. The completion of the reaction was analyzed by TLC (thin layer chromatography) spotting, and 30 mL of ice water was added to the reaction liquid to quench the reaction. The reaction solution was extracted with ethyl acetate, the water phase was taken, and the water was removed under reduced pressure with a rotary evaporator. The residue obtained after rotary evaporation was separated and purified by column chromatography to obtain the final target molecular product 1. Its reaction formula is as follows:

[0045]

Embodiment 3

[0047] Dissolve 100 mg of melatonin in 10 mL of acetonitrile, then add 137 mg of sodium carbonate and 136 mg of sodium bromoethylsulfonate, and stir the reaction overnight at 80°C. After the plate monitoring reaction is completed, the residue obtained by spinning and drying is separated and purified by column chromatography to obtain the target molecule 2, and its reaction formula is as follows:

[0048]

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Abstract

The invention discloses a melatonin derivative and a preparation method and application thereof. The preparation method comprises the following steps that natural melatonin is dissolved in a solvent,a catalyst is added at -2-2 DEG C, a stirring reaction is conducted, a reactant is added, the solvent is transferred to the place at 20-30 DEG C for a reaction, after an analytical reaction is completed through a thin layer chromatographic dot plate, ice water is added in reaction liquid for a quenching reaction, a water intake phase is extracted, rotary evaporation is conducted to remove water, residues are subjected to column chromatography separation and purification, and a final target molecular product is obtained. The water solubility of the prepared melatonin derivative is improved by near 700 times.

Description

technical field [0001] The invention relates to a melatonin derivative, a preparation method and application thereof, and belongs to the field of medicine preparation. Background technique [0002] Melatonin (also known as N-acetyl-5-methoxytryptamine) is an amine hormone produced by the pineal gland of mammals and humans, and its effects are quite extensive. It can maintain the circadian rhythm of the circadian rhythm, assist sleep, enhance human immunity, anti-aging, fight tumors, anti-mental diseases, and protect blood vessels. Melatonin is also an ancient indole plant hormone, which plays an important role in plant growth regulation and resistance to harsh environments. Melatonin also has a powerful antioxidant function and can be used as a cosmetic skin care product. According to research, the toxicity of melatonin is very small. Human experiments have shown that taking up to several grams a day for up to a month has almost no toxic side effects. Therefore, melatonin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/14A61P25/20A61P37/04A61P39/00A61P35/00A61P25/00A61P9/14A01N43/38A01P21/00
CPCA01N43/38A61P9/14A61P25/00A61P25/20A61P35/00A61P37/04A61P39/00C07D209/14
Inventor 李昱飞田云鹏张江虹李勤斌
Owner 李昱飞
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