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2‑amino‑1,3‑propanediol derivatives, their preparation, nanostructure, lead-expelling activity and applications

A technology of propylene glycol and amino group, applied in the field of biomedicine, can solve the problems of unfavorable industrialization, difficult completion, and difficult purification of products.

Inactive Publication Date: 2017-03-01
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since amino acids and sugars require two steps of enamination and reduction to complete the coupling, and these reactions of amino acids and sugars can only be carried out in water, the reaction is difficult to complete and the product is not easy to purify, which is not conducive to industrialization

Method used

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  • 2‑amino‑1,3‑propanediol derivatives, their preparation, nanostructure, lead-expelling activity and applications
  • 2‑amino‑1,3‑propanediol derivatives, their preparation, nanostructure, lead-expelling activity and applications
  • 2‑amino‑1,3‑propanediol derivatives, their preparation, nanostructure, lead-expelling activity and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1 prepares benzoylmethionine

[0024] Mix 5g (33.6mmol) of L-methionine and 3.56g (33.6mmol) of sodium carbonate, use tetrahydrofuran as a solvent, and adjust the pH to 9 with saturated sodium carbonate. Slowly add 6 mL of benzoyl chloride dropwise in 3 times with a constant pressure funnel under ice bath, and at the same time add 6 mL of saturated sodium carbonate each time to keep the pH at 9. Reaction 6h, filter. The filtrate was adjusted to pH 7 with saturated potassium hydrogen sulfate, concentrated under reduced pressure, the residue was adjusted to pH 2 with saturated potassium hydrogen sulfate, extracted 3 times with ethyl acetate, the ethyl acetate layer was washed 3 times with 5% potassium hydrogen sulfate aqueous solution, washed with saturated chlorine The sodium chloride aqueous solution was washed to pH 7, the ethyl acetate layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and th...

Embodiment 2

[0025] Embodiment 2 prepares aspartic acid dimethyl ester hydrochloride

[0026] In an ice bath, slowly drop 12.25mL (155mmol) of thionyl chloride into 150mL of anhydrous methanol. After activation for 0.5h, add 10g (75mmol) of L-aspartic acid in portions, stir at room temperature, and monitor to The starting material disappeared and the reaction was terminated. The reaction mixture was concentrated under reduced pressure and the residue was triturated repeatedly with ether to afford 13.33 g (90%) of the title compound as a colorless solid.

Embodiment 3

[0027] Embodiment 3 prepares dimethyl benzoyl methionyl aspartate

[0028] Under ice bath, dissolve 664mg (2.6mmol) benzoyl-L-methionine in anhydrous tetrahydrofuran, add 351mg (2.6mmol) 1-hydroxybenzotriazole (HOBt) and 740mg (3.5mmol) di Cyclohexylcarbodiimide (DCC), activated for 0.5h. Dissolve 540mg (2.7mmol) of L-aspartate dimethyl hydrochloride in anhydrous tetrahydrofuran, use NMM to adjust the pH to 8 and add it to the activation solution just obtained, then use NMM to adjust the pH to 8, remove the ice bath, and store at room temperature Reaction 12h. The reaction solution was filtered, the filtrate was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, filtered, the ethyl acetate layer was washed 3 times with saturated sodium bicarbonate solution, 3 times with saturated sodium chloride solution, and 3 times with 5% potassium bisulfate solution. Wash three times with saturated sodium chloride solution, three times with 5% sodium bicarbo...

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Abstract

The invention relates to 2-amino-1,3-propylene glycol derivatives, preparation, a nano structure, a lead-removing activity, and applications thereof. The invention discloses 2-amino-1,3-propylene glycol derivatives represented by the formula Ia-d, wherein in the formula the AA represents a L-met, L-Phe, L-Val, or L-Ser residue. The invention discloses a preparation method and nano structure of the derivatives, also discloses a stepwise stability constant between the derivatives and Pb (II) in complex reactions, and further discloses a lead removing effect of the derivatives in a mouse lead acetate poisoning model. So the 2-amino-1,3-propylene glycol derivatives can be taken as a lead dispelling agent in clinic. C6H5CO-AA-ASP[NHCH(CH2OH)2]-NHCH(CH2OH)2 Ia-d.

Description

[0001] field of invention [0002] The present invention relates to 2-amino-1,3-propanediol derivatives represented by Ia-d, wherein AA is L-Met, L-Phe, L-VaL, L-Ser residues, their preparation methods, and their The nanostructures involved in their stepwise stability constants for their complexation with Pb(II), and further involved in their lead-expelling effect on a mouse model of lead acetate poisoning. Therefore, the present invention clarifies the clinical application prospect of 2-amino-1,3-propanediol derivatives Ia-d as lead repellent. The invention belongs to the field of biomedicine. Background technique [0003] Lead in our food, water and air enters the blood through the digestive tract, respiratory tract and skin, and combines with tissue proteins to form lead-binding protein, which stimulates sensitive factors and leads to lead poisoning in the human body, threatening cognitive ability and neurobehavior. Lead-dispelling drugs (penicillamine, etc.) that are oft...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/062C07K5/065A61K38/05A61P39/02
Inventor 彭师奇赵明王玉记吴建辉郝程杰
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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