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Bicyclol-tiopronin ester and preparation method and applications thereof

A technology of tiopronin ester and tiopronin, applied in the directions of active ingredients of heterocyclic compounds, production of bulk chemicals, digestive system, etc., can solve the problems of low oral bioavailability, inability to make injections, poor water solubility of bicyclic alcohols, etc. , to achieve low cost, reduce the degree of acute liver injury, and good water solubility

Inactive Publication Date: 2014-04-09
NANJING TECH UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Bicyclol has poor water solubility, cannot be made into injections, and has low oral bioavailability, so it is not widely used

Method used

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  • Bicyclol-tiopronin ester and preparation method and applications thereof
  • Bicyclol-tiopronin ester and preparation method and applications thereof
  • Bicyclol-tiopronin ester and preparation method and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation of embodiment 1 bicyclic alcohol-tiopronin ester

[0023] (1) Tiopronin sulfhydryl protection

[0024]

[0025] Dissolve 2.03g (32mmol) of tiopronin in 30mL of anhydrous N,N-dimethylformamide (DMF), and add 4.22g (13.7mmol) of monomethoxytrityl chloride (Mmt-Cl) at room temperature After 3 hours of reaction, TLC detected that the reaction was complete. The reaction liquid was evaporated to dryness, and the obtained solid was washed successively with ether, recrystallized from methanol, and dried to obtain 4.93 g of white powdery solid. (2) Esterification reaction

[0026]

[0027] Dissolve 1.23 g (2.8 mmol) of the product obtained in step (1) in 20 mL of anhydrous dichloromethane (DCM), cool in an ice bath, add 4 mg of 4-dimethylaminopyridine (DMAP) (0.03 mmol) and 698 mg of 1-(3- Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) (3.64mmol), stirred for 10min, added 911mg of bicyclic alcohol (2.3mmol), reacted for 2h. The reactio...

Embodiment 2

[0032] Example 2 Effect of bicyclol-tiopronin ester on rat D-galactosamine liver injury model

[0033] 1. Experimental materials

[0034] 1.1 Animals

[0035] SPF grade SD rats, weighing 180g-220g, male and female, were provided by the Comparative Medicine Center of Nanjing Military Region General Hospital. They were randomly divided into 4 groups, 10 rats in each group, namely (1) blank control group, (2) model control group, (3) bicyclol group, (4) bicyclol-tiopronin axate group.

[0036] 1.2 Drugs

[0037] The bicyclic alcohol-tiopronin ester of embodiment 1, bicyclic alcohol.

[0038] 1.3 Drug preparation, dosage and grouping

[0039] (1) blank control group;

[0040] (2) Model control group;

[0041] (3) Bicyclol group: administration of bicyclol at a dose of 6.75 mg / kg (according to the clinical human daily dosage of 75 mg and converted into rat dosage according to body surface area);

[0042] (4) Bicyclol-tiopronin ester group: Bicyclyl-tiopronin ester was admini...

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Abstract

The invention discloses a bicyclol-tiopronin ester and a preparation method and applications thereof. The compound has a pharmacological activity similar to that of bicyclol, and is better in water solubility, therefore, the compound is higher in bioavailability. The method for preparing bicyclol-tiopronin ester provided by the invention comprises the steps of carrying out hydrosulphonyl protection on tiopronin firstly; then, carrying out esterification and condensation on carboxyl of the tiopronin subjected to hydrosulphonyl protection by using hydroxyls of bicyclol; and finally, carrying out hydrosulphonyl deprotection on the obtained product so as to obtain bicyclol-tiopronin ester. The method is convenient to operate, low in cost and high in yield; and the structure of the compound is shown in the description.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and organic chemistry, and relates to bicyclol-tiopronin ester and its preparation method and application. Background technique [0002] Bicyclic alcohol, the chemical name is 4,4'-dimethoxy-5,6,5',6'-dimethoxy-2-hydroxymethyl-2'-methoxycarbonylbiphenyl, its structural formula As follows (Me means methyl): [0003] [0004] Bicyclol is an artificially synthesized multifunctional and multi-target drug, which has significant liver-protecting and enzyme-lowering activities. Various studies on the mechanism of action of the drug have shown that the liver-protecting and enzyme-reducing mechanism of bicyclol is mainly through scavenging free radicals, thereby maintaining the integrity of cells, preventing liver cell nuclear DNA from damage and reducing the occurrence of apoptosis, thereby Play the role of liver protection. It is mainly used for various liver injuries, such as acute liver injury....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/68A61K31/36A61P1/16
CPCY02P20/55
Inventor 苏贤斌金凯军梁泽民赵兴猛叶青董海军
Owner NANJING TECH UNIV
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