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Paeoniflorin compound with inhibitory activity against abnormal expression of cyclooxygenase-2, its preparation method and application

A compound, the technology of paeoniflorin, applied in the field of medicinal chemistry, can solve the problems of not showing activity and limiting the medicinal properties of paeoniflorin

Active Publication Date: 2012-10-17
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in our drug research and development of paeoniflorin, we found that the compound does not show activity in vitro, only in vivo animal models can show activity, and paeoniflorin can only be effective in pre-administration, these characteristics limit the efficacy of paeoniflorin. druggability of glycosides

Method used

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  • Paeoniflorin compound with inhibitory activity against abnormal expression of cyclooxygenase-2, its preparation method and application
  • Paeoniflorin compound with inhibitory activity against abnormal expression of cyclooxygenase-2, its preparation method and application
  • Paeoniflorin compound with inhibitory activity against abnormal expression of cyclooxygenase-2, its preparation method and application

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Experimental program
Comparison scheme
Effect test

specific Embodiment

[0075] 1. Instruments and equipment

[0076] NOVOstar multifunctional microplate reader (BMG LABTECH, Germany);

[0077] Electrophoresis apparatus and semi-dry electroblotting tank (Bio-Rad Laboratories, Hercules, CA);

[0078] PCR machine (MJ Research, South San Francisco, CA);

[0079] Gel Imager (Furi Technology Company);

[0080] Olympus IX51 research grade inverted fluorescence microscope (Olympus, Japan);

[0081] Infrared spectrum: Perkin-Elmer 577 infrared spectrophotometer;

[0082] Mass spectrometer: Finnigan MAT-95, Finnigan LCQ-DECA mass spectrometer (low resolution ESI).

[0083] Nuclear magnetic resonance spectrum: Varian Mecury Plus-300 nuclear magnetic resonance instrument, Bruker AM-300 nuclear magnetic resonance instrument, δ (ppm), with TMS as internal standard;

[0084] LC-MS: Agilent 1100 liquid phase coupled bruker esquire mass spectrometer;

[0085] Analytical HPLC instrument: Waters 2690 Separate Model, Waters PDA 996 detector coupled with Alltch ...

Embodiment 1

[0098] Embodiment 1 compound DG synthetic method

Embodiment 11

[0100]

[0101] Paeoniflorin (1) (4.8g, 10mmol) was dissolved in DMF (30mL), TBSCl (1.5g, 10mmol) and imidazole (1.4g, 20mmol) were added, stirred at room temperature for 1 hour, and the reaction was monitored by TLC. After the reaction was complete, water was added, extracted with ethyl acetate, and the ester layer was washed with a saturated NaCl aqueous solution, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography (dichloromethane / methanol=15 / 1 (V / V)) to obtain 5.5 g of Compound 2 as a colorless oil. Yield: 93%.

[0102] Compound 2: ESI-MS: [M+Na]+: 617. 1 H-NMR (CDCl 3 , 300Hz, δppm): 8.18-7.83(m, 2H), 7.54(m, 1H), 7.48-7.31(m, 2H), 5.51(s, 1H), 4.82-4.35(m, 3H), 3.94-3.16 (m, 5H), 2.59(m, 1H), 2.37(m, 1H), 2.24-1.74(m, 3H), 1.34(s, 3H), 0.87(9H, s), 0.04(3H, s), 0.03(3H,s).

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Abstract

The invention belongs to the field of pharmaceutical chemistry and specifically relates to a paeoniflorin compound with an inhibitory activity against abnormal expression of cyclooxygenase-2, a synthetic method thereof and an application in preparation of nonsteroidal anti-inflammatory drugs and drugs for treating and preventing cerebral apoplexy and / or Parkinson's disease. The paeoniflorin compound has a structure as shown in the following general formula I.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and more specifically, relates to a paeoniflorin compound with COX-2 abnormal expression inhibitory activity, its synthesis method and its use in the preparation of non-steroidal anti-inflammatory drugs and for the treatment and prevention of stroke and and / or use in medicines for Parkinson's disease. Background technique [0002] Cyclooxygenase (COX) is a dual-functional enzyme with cyclooxygenase and catalase activities, which catalyzes the conversion of membrane phospholipid arachidonic acid (AA) into prostanoids. ) rate-limiting enzyme. Cyclooxygenase is an important metabolic enzyme involved in various physiological and pathological pathways including inflammation, pain, angiogenesis and blood pressure regulation. [0003] There are two isoenzymes of COX: COX-1 and COX-2. COX-1 is inherently expressed in almost all tissues, mediates the production of low-level physiological prostaglandi...

Claims

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Application Information

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IPC IPC(8): C07D493/08A61K31/4433A61K31/357A61P29/00A61P25/16A61P25/00
CPCC07D493/18A61P25/00A61P25/16A61P29/00
Inventor 叶阳冯林音葛凡蔡欣唐春萍李希强廖苍松柯昌强姚胜季新泉
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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