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1,3-dithiolane derivatives, synthesis, nano structure, activity, and application thereof as lead dispelling agent

A compound, ia-p technology, applied in 1,3-dithiolane derivatives, its synthesis, nanostructure, activity and use as lead expelling agent, can solve the problem of many reaction steps and low yield , is not conducive to industrialization and other issues

Inactive Publication Date: 2014-12-17
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The inventor's previous inventions showed that the preparation of conjugates of amino acids and 1,3-dithiolane requires many reaction steps and the yield is not high, which is not conducive to industrialization

Method used

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  • 1,3-dithiolane derivatives, synthesis, nano structure, activity, and application thereof as lead dispelling agent
  • 1,3-dithiolane derivatives, synthesis, nano structure, activity, and application thereof as lead dispelling agent
  • 1,3-dithiolane derivatives, synthesis, nano structure, activity, and application thereof as lead dispelling agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1 prepares dimethyl dimercaptosuccinate (1)

[0020] Dissolve 5.0 g (27.5 mmol) of dimercaptosuccinic acid (DMSA) powder in 200 mL of methanol, and feed freshly prepared dry HCl gas into the suspension under ice-cooling and stirring. After 2 hours of reaction, the reaction solution was clear, removed the ice bath, slowly returned to room temperature, and continued to stir for 6 hours. HCl and methanol were removed under reduced pressure, and the residue was washed with 10 mL of ether for three times. After filtration, the filter cake was recrystallized with 50% aqueous ethanol to obtain 4.5 g (77.6%) of the title compound as colorless needle crystals. ESI-MS(m / e): 211[M+H] + .

Embodiment 2

[0021] Example 2 Preparation of 4,5-dimethoxycarbonyl-2-(4-chlorophenyl)-1,3-dithiolane (Ia)

[0022] Dissolve 1.68g (12mmol) of 4-chlorobenzaldehyde and 2.11g (10mmol) of meso-dimethyl dimercaptosuccinate (1) in 50mL of methanol, and slowly add 1mL of concentrated sulfuric acid dropwise under stirring. After stirring at room temperature for 24 hours, with saturated NaHCO 3 The solution was adjusted to pH 7, concentrated under reduced pressure, 30 mL of ethyl acetate was added to dissolve the residue, washed three times with 50 mL of water, and then washed three times with 50 mL of saturated sodium chloride solution, the ethyl acetate phase was dried with anhydrous sodium sulfate for 2 hours, and filtered. The filtrate was concentrated under reduced pressure to obtain a pale yellow residue, which was purified by silica gel column chromatography (petroleum ether: ethyl acetate, 5:1) to obtain 2.25 g (68%) of the title compound as a colorless solid. ESI-MS(m / e): 333[M+H] + .Mp...

Embodiment 3

[0023] Example 3 Preparation of 4,5-dimethoxycarbonyl-2-(4-methylphenyl)-1,3-dithiolane (Ib)

[0024] Dissolve 1.44g (12mmol) of 4-methylbenzaldehyde and 2.11g (10mmol) of meso-dimethyl dimercaptosuccinate (1) in 50mL of dichloromethane, and slowly add 2mL of trifluoroacetic acid dropwise under stirring. After stirring at room temperature for 48 hours, with saturated NaHCO 3 The solution was adjusted to pH 7, concentrated under reduced pressure, 30 mL of ethyl acetate was added to dissolve the residue, washed three times with 50 mL of water, and then washed three times with 50 mL of saturated sodium chloride solution, the ethyl acetate phase was dried with anhydrous sodium sulfate for 2 hours, and filtered. The filtrate was concentrated under reduced pressure to obtain a colorless residue, which was purified by silica gel column chromatography (petroleum ether: ethyl acetate, 5:1) to obtain 2.05 g (66%) of the title compound as a colorless solid. ESI-MS(m / e): 313[M+H] + .Mp:...

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Abstract

The invention relates to 1,3-dithiolane derivatives, synthesis, a nano structure, an activity, and an application thereof as a lead dispelling agent. The invention discloses 16 1,3-dithiolane derivatives represented by the formula Ia-p, wherein in the formula the R1 represents 4-chlorophenyl, 4-methoxylphenyl, phenyl, 4-isopropylphenyl, 2,6-dimethoxylphenyl, 3,5-dimethoxylphenyl, or 2,4,6-trimethoxylphenyl, and the R2 represents CO2CH3 or CH2OH; and also discloses preparation, a nano structure, and a lead removing activity of the derivatives. So the 1,3-dithiolane derivatives are advantageously used as a lead dispelling agent in clinic.

Description

field of invention [0001] The present invention relates to 16 kinds of novel 1,3-dithioheterocyclic derivatives represented by Ia-p, R in the formula 1 Selected from 4-chlorophenyl, 4-methylphenyl, 4-methoxyphenyl, phenyl, 4-isopropylphenyl, 2,6-dimethoxyphenyl, 3,5-di Methoxyphenyl, 2,4,6-trimethoxyphenyl, R 2 from CO 2 CH 3 , CH 2 OH, concerning their preparation methods, nanostructures and in vivo lead-displacement activity, and further their use as lead repellents. Therefore, the present invention relates to the prospect of clinical application of 16 novel 1,3-dithioheterocyclic derivatives (Ia-p) as lead repellent drugs. The invention belongs to the field of biomedicine. Background technique [0002] In recent years, with the rapid growth of population, the rapid development of industry, and the abuse of pesticides and fertilizers, a large number of harmful heavy metals have been discharged one after another, causing environmental pollution. These harmful substan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/06A61K31/381A61P39/02B82Y5/00
CPCC07D339/06
Inventor 赵明彭师奇王玉记吴建辉潘璟
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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