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Preparation of dienyl mesyloxy oleanane alcohol and medical application of dienyl mesyloxy oleanane alcohol in resisting hepatitis B

A technology of diene methanesulfonyloxy oleanane and methanesulfonyloxy oleanane, which is applied in the field of preparation of diene methanesulfonyloxy oleanol, can solve the problems that have not been effectively developed and other issues, to achieve the effects of clear industrialization prospects, inhibition of duplication, and wide distribution

Inactive Publication Date: 2020-11-10
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above pharmacological studies or clinical application studies all use this natural product or its derivatives as liver-protecting drugs, and its structurally modified derivatives have been reported in relatively few literatures in antiviral treatment. Oleanolic acid derivatives treat DNA-like virus infections , especially its new application for anti-hepatitis B virus (comprising inhibition of hepatitis B HBsAg and / or HBeAg antigen, inhibition of HBV-DNA replication) has not been effectively developed, so from oleanolic acid derivatives to find the field of anti-hepatitis B virus Active compounds, that is to say, such structural modification to have anti-DNA virus activity is a new field

Method used

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  • Preparation of dienyl mesyloxy oleanane alcohol and medical application of dienyl mesyloxy oleanane alcohol in resisting hepatitis B
  • Preparation of dienyl mesyloxy oleanane alcohol and medical application of dienyl mesyloxy oleanane alcohol in resisting hepatitis B
  • Preparation of dienyl mesyloxy oleanane alcohol and medical application of dienyl mesyloxy oleanane alcohol in resisting hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 : the preparation of formula (1) compound 3-methylsulfonyloxy oleanane 11,13 (18)-diene-28-alcohol 1.1 instruments and reagents

[0031] The ultraviolet spectrum was measured with a Shimadzu UV-240 ultraviolet spectrophotometer; the nuclear magnetic resonance spectrum was measured by an INOVA type superconducting nuclear magnetic resonance spectrometer (VARIAN INOVA-400MHz) (tetramethylsilyl ether TMS was the internal standard); electrospray mass spectrometry ESI- MS was determined by Bruker Esquire 3000+ mass spectrometer; silica gel for column chromatography (100-200, 200-300 and 300-400 mesh) and silica gel GF254 for thin-layer chromatography (10-40 mesh) were all produced by Qingdao Ocean Chemical Factory The reagents used are all analytically pure, wherein petroleum ether boiling range is 60~90 ℃; High performance liquid phase detection (HPLC) uses Agilent 1100 instrument; Preparative thin layer chromatography (PTLC) uses the aluminum foil silica gel plat...

Embodiment 2

[0042] Example 2 : the inhibitory effect of formula (1) compound on hepatitis B surface antigen (HBsAg)

[0043] 2.1 Cell culture:

[0044] HepG2.2.15 cells were cultured in DMEM medium containing 10% inactivated fetal bovine serum, 100 U / ml penicillin and 100 U / ml streptomycin, and 100 μg / ml G418 at 37°C, 5% CO 2 , cultured in an incubator with 100% relative humidity.

[0045] 2.2 Determination of the inhibitory effect of the test sample on the HBsAg secreted by HepG2.2.15 cells:

[0046] Take the HepG2.2.15 cells in the logarithmic growth phase, and dilute the cells to 1×10 with medium 5 / ml, seeded in 96-well cell culture plate, 100ml per well, at 37°C, 5% CO 2 After culturing in an incubator with 100% relative humidity for 24 hours, add the test sample diluted with the medium, set up three replicate holes for each concentration, 200 microliters per hole, place at 37°C, 5% CO 2 , cultivated in an incubator with 100% relative humidity, change the culture medium contain...

Embodiment 3

[0053] Example 3 : the inhibitory effect of formula (1) compound on hepatitis B e antigen (HBeAg)

[0054] 3.1 Cell culture: the method is the same as in Example 2.

[0055] 3.2 Determination of the inhibitory effect of the test sample on the HBeAg secreted by HepG2.2.15 cells:

[0056] Take the HepG2.2.15 cells in the logarithmic growth phase, and dilute the cells to 1×10 with medium 5 / ml, seeded in 96-well cell culture plate, 100ml per well, at 37°C, 5% CO 2 After culturing in an incubator with 100% relative humidity for 24 hours, add the test sample diluted with the medium, set up three replicate holes for each concentration, 200 microliters per hole, place at 37°C, 5% CO 2 , cultivated in an incubator with 100% relative humidity, change the culture medium containing the same concentration sample every 4 days, mix the same volume of the culture medium with the same concentration of the same sample and the same concentration, and use it as the sample to be tested. On t...

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Abstract

The invention relates to preparation of dienyl mesyloxy oleanane alcohol and a medical application of the dienyl mesyloxy oleanane alcohol in resisting hepatitis B. Particularly, the invention provides an application of 3[beta]-mesyloxy oleanane 11,13(18)-dien-28-ol in preparation of a medicine for preventing and treating hepatitis B virus infected diseases. The intensity of the compound for inhibiting the secretion of HBsAg and HBeAg under the concentration of 100 micrograms / milliliter exceeds that of positive drugs alpha-interferon and lamivudine; and when the test concentration is only 1 / 50(2.0 micrograms / milliliter) of the highest test concentration of the lamivudine, the inhibitory activity of the compound on HBV-DNA replication is as high as 44.1%. It is showed that the dienyl mesyloxy oleanane alcohol can be expected to be used for preparing non-nucleoside medicines for treating the hepatitis B virus infected diseases; specifically, the compound has an application for preparingan HBV-DNA inhibitor, an HBsAg inhibitor and an HBeAg inhibitor; and the preparation method is simple in steps, low in cost, wide in raw material source and easy for industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular, the invention relates to the preparation of diene methanesulfonyloxy oleanol and its medicinal application for anti-hepatitis B. The compound is a pentacyclic triterpene acid derivative with 3β-methylsulfonyloxy oleanane 11,13(18)-dien-28-ol synthesized from oleanolic acid as a starting material. It has the exact activity of inhibiting the secretion of HBsAg and HBeAg from HepG2.2.15 cells, and can significantly inhibit the replication of HBV-DNA in HepG2.2.15 cells. It can be expected to be used to prepare HBsAg and HBeAg, inhibit HBV-DNA replication, and treat hepatitis B Use of non-nucleoside innovative drugs for viral infection diseases. Background technique [0002] Hepatitis B is an infectious disease caused by hepatitis B virus (HBV, hepatitis B virus), so it is also called viral hepatitis B. HBV is a member of the hepadnaviridae family of hepadnaviridae. It is a partial ...

Claims

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Application Information

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IPC IPC(8): A61K31/56C07J63/00A61P31/20
CPCA61K31/56C07J63/008A61P31/20
Inventor 卢昂巫秀美魏永凯王朋川张汉超李辉王斌王彬赵昱
Owner DALI UNIV
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