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(S)-2-substituted-(3'-acetyl-2'-pyridone-1'-yl) acetic acid as well as preparation method and application thereof

A pyridone, acetyl technology, applied in the field of biomedicine, can solve problems such as promoting iron excretion

Inactive Publication Date: 2012-12-12
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The inventors have recognized that the use of (S)-2-substituted-(3'-acetyl-2'-pyridinon-1'-yl)acetic acid as an iron repellant may enhance iron excretion

Method used

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  • (S)-2-substituted-(3'-acetyl-2'-pyridone-1'-yl) acetic acid as well as preparation method and application thereof
  • (S)-2-substituted-(3'-acetyl-2'-pyridone-1'-yl) acetic acid as well as preparation method and application thereof
  • (S)-2-substituted-(3'-acetyl-2'-pyridone-1'-yl) acetic acid as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 12-(2,2-dimethoxy-ethyl)-5,5-dimethyl-1,3-dioxane

[0041]Add 4.92g (30mmol) of 1,1,3,3-tetramethoxypropane, 0.78g (7.5mmol) of 2,2-dimethyl-1,3-propanediol into 25ml of dichloromethane, drop into 0.1ml (6N) hydrochloric acid, stirred at room temperature for 24 hours, added 0.78g (7.5mmol) 2,2-dimethyl-1,3-propanediol, continued to stir at room temperature for 24 hours, added 4.0g of anhydrous sodium carbonate, stirred for 2 hours, After filtration and concentration to remove the solvent, the residue was subjected to silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) to obtain 2.059 g of a colorless liquid with a yield of 67%.

Embodiment 22

[0042] Example 22-Acetaldehyde-5,5-dimethyl-1,3-dioxane (1)

[0043] Add 2.04g (10.0mmol) of 2-(2,2-dimethoxy-ethyl)-5,5-dimethyl-1,3-dioxane into 50ml of acetonitrile, then add 98mg (0.43 mmol) DDQ and 5ml of water, stirred in a water bath at 50°C for 2 hours, TLC showed that the raw materials basically disappeared, took it out to cool to room temperature, added 200ml of water, extracted with dichloromethane (50ml×6), and dried the extract over anhydrous sodium sulfate , filtered, and the solvent was removed by rotary evaporation, and the residue was subjected to silica gel column chromatography (petroleum ether (30-60°C): ether = 4:1) to obtain 1.27 g of a colorless liquid, with a yield of 80%. ESI-MS(m / e): 159.3[M+H] + , 181.4[M+Na] +

Embodiment 318

[0044] The preparation general method of embodiment 318 kinds of L-amino acid methyl ester hydrochloride 2a-r

[0045] Add 3.75ml (50mmol) of thionyl chloride dropwise to 50ml of anhydrous methanol under ice bath. After the dropwise addition is completed within 30min, add 42mmol of L-amino acid in batches, stir at room temperature for 24h, TLC (CHCl 3 : MeOH=2:3) monitor until the disappearance of the raw material to terminate the reaction. The water pump pumps away the unreacted thionyl chloride SOCl 2 and HCl, repeatedly triturated with ether to obtain a white solid, recrystallized from methanol-ether to obtain L-amino acid methyl ester hydrochloride as a white solid (proline methyl ester hydrochloride is a colorless viscous oil). According to this general method, HCl·Phe-OMe, HCl·Ala-OMe, HCl·Gly-OMe, HCl·Arg-OMe, HCl·Asp-(OMe) were synthesized 2 , HCl Leu-OMe, HCl Met-OMe, HCl Ser-OMe, HCl Tyr-OMe, HCl Thr-OMe, HCl Ile-OMe, HCl Trp-OMe, HCl Val-OMe, HCl Pro-OMe, HCl His...

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Abstract

The invention discloses (S)-2-substituted-(3'-acetyl-2'-pyridone-1'-yl) acetic acid as well as a preparation method and application thereof. The preparation method thereof comprises the following steps of preparing N-acetoacetyl-L-amino acid methyl ester by condensing L-amino acid methyl ester and dicthenone; preparing N-[2-(5,5-dimethyl-1,3 dioxane-diyl-)vinyl]-N-acetoacetyl-L-amino acid methyl ester through reaction between N-acetoacetyl-L-amino acid methyl ester and 2-glyoxyl-5,5-dimethyl-1,3-dioxane; preparing (S)-2-substituted-(3'-acetyl-2'-pyridone-1'-yl) methyl acetate by the N-(2-(5,5-dimethyl-1,3 dioxane-diyl-)vinyl)-N-acetoacetyl-L-amino acid methyl ester; obtaining the (S)-2-substituted-(3'-acetyl-2'-pyridone-1'-yl) acetic acid by saponifying the (S)-2-substituted-(3'-acetyl-2'-pyridone-1'-yl) methyl acetate. A high-iron animal model is adopted to evaluate the detoxification activity when iron poisoning occurs in a compound body. An experimental result shows that the compound has excellent iron expulsion action and can be clinically used as antidote in the process of iron poisoning.

Description

technical field [0001] The present invention relates to N-substituted pyridone compounds, in particular to (S)-2-substituted-(3'-acetyl-2'-pyridone-1'-yl)acetic acid and its preparation method, and the present invention also relates to them The application as a heavy metal repellent belongs to the field of biomedicine. Background technique [0002] Excess iron or iron accumulation in human tissues can lead to organ dysfunction and cause serious conditions such as hemochromatosis, beta-thalassemia, neurodegenerative diseases, myelodysplastic syndrome, alcoholic liver disease and related kidney diseases . Furthermore, iron accumulation in the body leads to free radical mediated tissue / organ damage and eventually death. At present, iron chelation therapy is the only treatment method, and N-substituted pyridone compounds have various physiological activities, such as sterilization, analgesia, anti-tumor and treatment of Parkinson's disease. Since this type of pyridone compoun...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/64C07D401/06A61K31/4412A61K31/444A61K31/4439A61P39/02
Inventor 彭师奇赵明李响敏吴建辉
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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