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Triterpene derivative and preparation method and application

A use and compound technology, applied in the field of triterpenes and their derivatives, can solve the problems that the biological activity of triterpenoids has not been reported, and prevent the spread of HIV virus, etc.

Inactive Publication Date: 2013-06-05
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Triterpenoids have attracted more and more attention due to their diverse biological and pharmacological activities, such as betulinic acid and its derivatives have been used as anti-tumor and anti-HIV drugs in clinical trials (U.S.Pat.Nos. 5,679,828; 6,689,767; and 6,369,109; and U.S.App.Pub.No.2004 / 0204389); oleanolic acid is an effective ingredient for protecting the liver from chemical reagent damage and preventing HIV infection (Liu, J., Journal of Ethnopharmacology, 110: 92-94 (2005)); Another example is maslinic acid, recently a European experiment reported that it can block HIV virus transmission in the body, and the effective rate reaches more than 80%, but the biological activity of triterpenoids in hepatitis C has not been reported so far. See the report

Method used

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  • Triterpene derivative and preparation method and application
  • Triterpene derivative and preparation method and application
  • Triterpene derivative and preparation method and application

Examples

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preparation example Construction

[0072] The preparation method of the compound of the present invention

[0073] Another aspect of the present invention provides a method for preparing the above compound.

[0074] The triterpene compounds and derivatives involved in the present invention can be extracted from natural plants, and / or chemically synthesized, semi-synthesized or structurally modified. In one embodiment of the invention, some triterpenoids can be obtained by extracting from plants or purchased from the market, and some other triterpenes can be obtained by structural modification or chemical synthesis or semi-synthesis of the above-mentioned triterpenoids.

[0075] The extraction method includes immersing triterpenoid-rich plants in a polar solvent to reflux, filtering to remove insoluble matter, concentrating, acid treatment, and finally separating the triterpenoids by silica gel column chromatography (e.g. dichloromethane / methanol gradient elution). Terpene aglycone. Those skilled in the art ha...

Embodiment 1

[0147] Example 1 Synthesis of echinocytic acid-glucose derivatives

[0148]

[0149] Take 3g of D-glucose in a 50mL reaction bottle, add 24mL of pyridine to dissolve it, add 12mL of acetic anhydride in turn, and a catalytic amount of DMAP, and stop the reaction after overnight reaction at room temperature. TLC monitoring, developer PE:EA=1:1. After the solvent was spin-dried, 20mL of the developing agent (PE:EA=1:1) was dissolved and separated by a flash column for use.

[0150] Take 390mg of the above product in a 25mL reaction bottle, dissolve in 3mL DCM, slowly add 0.21mL of HBr-HOAc solution dropwise under ice bath, react for 1h, place it at room temperature for reaction, monitor by TLC, developer PE:EA=2:1. After 12 hours of reaction, the reaction was stopped. After adding 20mL DCM to dilute, successively add 20mL distilled water, 20mL saturated NaHCO 3 Solution washing, combined organic layers, MgSO 4 After drying, column separation and purification, the developme...

Embodiment 2

[0156] Example 2 Synthesis of echinocytic acid-glucose derivatives by click reaction

[0157] Reagents and reaction conditions: (a) TBTU, DIEA, prop-2-yn-1-amine, THF, rt; (b) CuSO 4 ,sodium L-ascorbate,CH 2 Cl 2 -H 2 O, rt; (c) 4NaOH, MeOH, rt.

[0158] operate:

[0159] (a) Dissolve 472mg (1mmol) of EA in 10mL of THF, add 385mg (1.2mmol) of TBTU and 0.4mL (2.4mmol) of DIEA, stir the reaction at room temperature for 3h until the reaction of EA is complete, then add 0.13mL of propargylamine into the system (2mmol), continue to react for 0.5h until the reaction is complete. The precipitate was filtered off, the filtrate was concentrated under reduced pressure, the sample was mixed with silica gel column chromatography, petroleum ether: ethyl acetate = 2:1, and 458 mg of white solid product 2 was obtained, with a yield of 90%. 1 H NMR (400MHz, CDCl 3 ):δ0.79,0.81,0.91,0.93,0.95,1.00,1.38(s,7×CH 3 ),0.73-2.30(m,other aliphatic ring protons),2.21(t,1H,J=2.6Hz),2.70(dd,1...

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Abstract

The invention relates to one type of triterpene, a derivative of the triterpene, a preparation method of the triterpene and the derivative of the triterpene, application in prevention and treatment of viral hepatitis and in particular to the application in treatment and prevention of viral hepatitis C. The triterpene and the derivative of the triterpene are compounds or salts or aquo-complexes of the salts like a structural formula 1 and a structural formula 2 expressed by an instruction book, wherein, the salts or aquo-complexes of the salts can be accepted in pharmacy. A substituent group and symbols are showed in definition of the instruction book.

Description

technical field [0001] The present invention relates to a class of triterpenes and their derivatives, their preparation method and their application in the prevention and treatment of viral hepatitis, especially the treatment and prevention of viral hepatitis C. Background technique [0002] Hepatitis C virus (HCV) is a particulate, single-stranded positive-sense RNA virus belonging to the genus Hepacivirus in the family Flaviviridae. The total length of its gene is about 9600 nucleotides, including two non-coding sequences at the terminal base and a single open reading frame (open reading frame, OPR). This open reading frame encodes a polyprotein with a total length of 3010 amino acids. Hepatitis C virus can be divided into six genotypes-I, II, III, IV, V and VI according to the difference in its sequence, of which genotype I is the most widely distributed in the world and accounts for about 75%. Each genotype is divided into different subtypes, of which type I is divided...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/56A61K31/58A61K31/7056A61K31/7024A61K31/724A61K31/7008A61P31/14C07J63/00
Inventor 周德敏肖苏龙张镇俞飞王晗王琪彭逸云张礼和
Owner PEKING UNIV
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