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Pyridine compound and its preparation method and anti-gastric cancer application

A compound and pyridine technology, applied in the pyridine compound WXSA-051B and its preparation, anti-gastric cancer application field, can solve the problems of poor cell permeability, complicated interpretation of biological research, lack of selectivity, etc., and achieve reduced migration ability , novel structure, and the effect of inhibiting RBP2 enzyme activity

Active Publication Date: 2020-04-14
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Other molecules inhibit KDMs in a competitive manner with 2-OG, such as N-oxalylglycine (NOG), 2,4-pyridinedicarboxylic acid (2,4-PDA), lack of selectivity or poor cell permeability, making the use of these Complicating the Interpretation of Biological Studies of Compounds

Method used

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  • Pyridine compound and its preparation method and anti-gastric cancer application
  • Pyridine compound and its preparation method and anti-gastric cancer application
  • Pyridine compound and its preparation method and anti-gastric cancer application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of embodiment 1 WXSA-051B

[0034] One, the preparation of intermediate 2

[0035] Take a 25mL round-bottomed flask, weigh 4-methoxy-2-picolylamine hydrochloride (1 g, 4.9 mmol) and potassium carbonate (1 g, 7.2 mmol) in 10 mL of acetonitrile, and stir at room temperature for 15 minutes; Then, 25 mL of acetonitrile solution dissolved with 3-bromopropyne (0.29 g, 2.5 mmol) was added dropwise to the aforementioned mixture using a constant pressure dropping funnel, and stirring was continued at room temperature overnight (new spots were detected by TLC). After the reaction was completed, the solvent was evaporated to dryness under reduced pressure, 50 mL of water was added to it, and 35 mL of ethyl acetate was added each time for extraction three times. The organic phases were combined and washed with saturated brine, then dried with anhydrous sodium sulfate, filtered and then rotary evaporated under reduced pressure. The sample was mixed, packed in a colu...

Embodiment 2

[0040] Example 2 Detecting the Effect of Compounds on RBP2 Enzyme Substrates in Gastric Cancer Cells (Western blot)

[0041] Purpose:

[0042] The effect of the test compound on the RBP2 enzyme substrate H3K4me3

[0043] Experimental Materials:

[0044] RPMI 1640 medium was purchased from Gibco;

[0045] Fetal bovine serum was purchased from Gibco;

[0046] DMSO was purchased from Sigma;

[0047] EpiQuik Total Histone Extraction Kit (OP-0006-100) was purchased from Epigentek Group;

[0048] Pierce ® BCA Protein Assay Kit was purchased from Thermo fisher scientific company

[0049] laboratory apparatus:

[0050] HF safe biological safety cabinet,

[0051] MCO-15AC carbon dioxide incubator, Japan Sanyo SANYO,

[0052] Polyacrylamide gel vertical electrophoresis tank, Liuyi Instrument Factory, Beijing, China

[0053] Test drug:

[0054] Compound WXSA-051B was prepared as a stock solution with DMSO, with a final concentration of 200mM. When used, it was diluted with in...

Embodiment 3

[0064] Example 3 Detection of compound's effect on migration ability in gastric cancer cells (Transwell)

[0065] Purpose:

[0066] The effect of detection compounds on the migration ability of gastric cancer cells

[0067] Experimental Materials:

[0068] RPMI 1640 medium was purchased from Gibco;

[0069] Fetal bovine serum was purchased from Gibco;

[0070] DMSO was purchased from Sigma;

[0071] Corning Transwell 3542 chamber was purchased from Beijing Suo Laibao Technology Co., Ltd.

[0072] laboratory apparatus:

[0073] HF safe biological safety cabinet,

[0074] MCO-15AC carbon dioxide incubator, Japan Sanyo SANYO,

[0075] Olympus CKX53 biological microscope, Shanghai Puhe Optoelectronics Technology Co., Ltd.,

[0076] Test drug:

[0077] For compound WXSA-051B, the sample was prepared into a mother solution with DMSO, with a final concentration of 200mM. When used, it was diluted with incomplete medium, and the final concentration of DMSO did not exceed 0.1%...

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Abstract

The present invention provides a pyridine compound WXSA‑051B designed and synthesized against the enzyme active site to inhibit the enzyme activity of RBP2, and also provides its preparation method. The test proves that the compound can increase the H3K4me3 protein level in human gastric cancer cell BGC‑823 Significantly increased, it has obvious inhibitory effect on RBP2 enzyme activity, and can reduce the migration ability of human gastric cancer cell BGC‑823. The compound of the present invention can be used as a gastric cancer inhibitor to prepare anti-gastric cancer drugs. The compound structure is as follows.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and specifically relates to a pyridine compound WXSA-051B, a preparation method thereof, and an anti-gastric cancer application. Background technique [0002] Antineoplastic drugs commonly used in clinical practice are mainly cytotoxic drugs, most of which have unavoidable disadvantages such as poor selectivity, strong toxic and side effects, and easy drug resistance. In recent years, with the rapid development of life science research, various basic processes such as signal transduction in malignant tumor cells, regulation of cell cycle, induction of apoptosis, angiogenesis, and interaction between cells and extracellular matrix are being investigated. The gradual clarification has brought about a huge change in the research and development concept of anticancer drugs. Therefore, using some key enzymes / proteins related to tumor cell modification as drug targets, screening and discovering ne...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12A61P35/00A61K31/4439
CPCA61P35/00C07D401/12
Inventor 贾继辉展鹏刘新泳陈春燕贾夏夏张硕俞霁王学顺
Owner SHANDONG UNIV
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