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12beta-hydroxy-androstane4,14-diene-16-ketone compounds and application thereof

A kind of ketone compound and compound technology, applied in the field of 12β-hydroxy-androsta 4,14-dien-16-one compound

Active Publication Date: 2018-09-21
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Driven by the interest in discovering new drug lead compounds, pre-biological activity screening found that dotenandrosterone compounds have significant immunosuppressive activity; the dotenandrosterone compounds provided by the present invention and their immunosuppressive drugs have not been reported yet

Method used

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  • 12beta-hydroxy-androstane4,14-diene-16-ketone compounds and application thereof
  • 12beta-hydroxy-androstane4,14-diene-16-ketone compounds and application thereof
  • 12beta-hydroxy-androstane4,14-diene-16-ketone compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Preparation of 12β-hydroxy-androst 4,14-dien-16-one compounds

[0027] Take 6kg of Simaoteng dry powder, reflux extraction with volume concentration 75% ethanol for 3 times, each time for 48h, filter and remove the filter residue, combine the filtrate extracted three times, concentrate under reduced pressure and then extract with ethyl acetate for 3 times, concentrate the ethyl acetate extraction layer Weighed to obtain 72g; the ethyl acetate layer extract was roughly divided with macroporous adsorption resin D101, and eluted with aqueous methanol solutions with volume concentrations of 20%, 40%, 60%, 80%, and 100% to obtain a total of 5 Parts (Fr.A, Fr.B, Fr.C, Fr.D, Fr.E); Fr.D part is obtained by gradient elution of the liquid phase with a volume concentration of 60%-100% methanol aqueous solution to obtain five parts Fr.D1-D5; then pass Fr.D2 through a 40-60 mesh silica gel column, and use chloroform-acetone (volume ratio 5:1-1:1) as the eluent to elute, ...

Embodiment 2

[0035] Embodiment 2: Immunosuppression detection test

[0036] (1) Preparation of spleen lymphocyte suspension

[0037] Take 18-22g of healthy BABL / c mice and kill them by bloodletting, put them in 75% alcohol for 5 minutes and sterilize them, take them out, put them in a sterile tray with the left side up, and clamp them with sterilized tweezers in an ultra-clean bench. Remove the fur in the middle of the abdomen, make an incision, use another set of instruments to cut open the layers of the abdominal wall, use the third set of instruments to take out the spleen, remove fat and connective tissue, put it in PBS (phosphate buffer saline), and wash away the floating blood Then move the spleen tissue to a plate containing RPMI 1640 incomplete culture medium, cut it into small pieces with scissors, grind the spleen in a 200-mesh stainless steel screen with a sterile syringe core, wash it with a small amount of PBS several times, Transfer the suspension to a 15mL centrifuge tube w...

Embodiment 3

[0066] Embodiment 3: in vitro antitumor activity test

[0067] (1) Material

[0068] DMSO (Sigma, USA), fetal bovine serum (HyClone, USA), RPMI-1640 culture medium (HyClone, USA), phosphate buffer (Shanghai beyotime Corporation), double antibody (HyClone, USA), CCK-8 (East Ren Chemical Technology Co., Ltd.), human tumor cells (CCRF-CEM, MOLT-4, K-562, MALME-3M, UACC-62, SNB-75, OVCAR8, EKVX, U0-31, SF-295, NCI-H226 , SK-OV3, MDA_MB-468, Hop92), the compound of the present invention and dexamethasone are all prepared with DMSO.

[0069] (2) method

[0070] Take 5 kinds of human tumor cells in the logarithmic growth phase and adjust the cell suspension to a certain concentration and inoculate them in a 96-well culture plate, 90 μl / well, culture for 24 hours, and then add different concentrations of compounds, 10 μl / well, each For each concentration, 3 replicate wells were set. Count the cells and determine the survival rate of the cells using the disc blue staining method, t...

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Abstract

The invention discloses 12beta-hydroxy-androstane4,14-diene-16-ketone compounds or pharmaceutically acceptable salt thereof, and the application of the compounds to preparation of immunosuppressive medicines and anti-tumor medicines. The compounds are extracted and separated from epigynum plants, and the structural formula is as shown in the specification, wherein R is selected from hydrogen, methoxyl, ethyoxyl, halogen, aliphatic group and fat amino; and in the formula, the formula as shown in the description represents single bond or double bonds. The experiment proves that the compounds reported in the invention have high immunosuppressive activity and anti-tumor activity; and the compounds provided by the invention provide leading compounds for developing immunosuppressive preparationsand anti-tumor preparations, and are favorable for developing and utilizing plant medicinal resources.

Description

technical field [0001] The invention relates to a class of 12β-hydroxyl-androst 4,14-dien-16-one compounds or pharmaceutically acceptable salts thereof and their application in the preparation of immunosuppressive and antitumor drugs. Background technique [0002] The immune response is originally a defense response for the body to protect itself and stabilize itself. Long-term suppression of this response will lead to some serious consequences such as infection and tumor induction, which are also some problems encountered by current immunosuppressants. Immunosuppressants provide effective therapeutic drugs for autoimmune diseases and rejection after organ transplantation in clinic, and are usually used to suppress rejection after organ transplantation, treat graft-versus-host disease after bone marrow transplantation, or treat Rheumatoid arthritis, Crohn's disease and other autoimmune diseases generally use drugs for immunosuppression. [0003] At present, there are more t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00A61P35/00A61P37/06
CPCA61P35/00A61P37/06C07J1/0007
Inventor 程桂广杨美莲曹建新高飞万宗姚元成赵天瑞张宏赵燕
Owner KUNMING UNIV OF SCI & TECH
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