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Andrographolide derivative, salt, preparation method and application thereof

A technology of andrographolide and its derivatives, applied in chemical instruments and methods, drug combinations, pharmaceutical formulations, etc., can solve problems such as toxic side effects and quality control difficulties, and achieve good biological activity

Active Publication Date: 2009-10-07
SUZHOU LEINA PHARMA RES DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Lianbizhi and Chuanhuning partially changed the structure of andrographolide, and showed different degrees of toxic and side effects in clinical use, while the main component of Xiyanping injection is a group of total sulfonates, including dozens of compounds , which brings great difficulties to quality control

Method used

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  • Andrographolide derivative, salt, preparation method and application thereof
  • Andrographolide derivative, salt, preparation method and application thereof
  • Andrographolide derivative, salt, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] This example discloses the preparation process of 19-O-phosphate monosodium salt-14-O-methylandrographolide

[0034] 1.1. Synthetic route design

[0035]

[0036] 1.2.3, Preparation of 19-O-isopropylidene andrographolide (CXL-1)

[0037]

[0038] Andrographolide (5.0 g, 14.3 mmol) was dissolved in dry DMF (100 mL), DMP (20 mL, 0.16 mol) and p-TsOH (272.0 mg, 1.4 mmol) were added under argon protection, and the reaction was stirred overnight at room temperature. After the reaction was detected by TLC, triethylamine (1 mL) was added to terminate the reaction. The reaction solution was diluted with EtOAc (200ml), washed with saturated NaHCO 3 (3×100mL), washed with saturated brine (2×100mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated by silica gel column chromatography (3:1-1:1, petroleum ether-EtOAc) to give white solid CXL-1 (4.54 g, 81.5%). R f 0.53 (1:1, Petroleum ether-EtOAc,).

[0039] 1 H NMR (500MHz, DMSO): δ...

Embodiment 2

[0058] Weigh 1 g of CXL-5, dissolve it in MeOH (20 mL), add 1M KOH in MeOH dropwise under ice-cooling, adjust the pH to 8.5-9.0, and naturally rise to room temperature and stir overnight. The methanol solution of 1M HCl was added dropwise to pH = 7.0 to terminate the reaction, the solvent was distilled off under reduced pressure, and the 2 O / isopropanol, H 2 O / acetone recrystallized several times to obtain 14-O-methylandrographolide-19-O-phosphate monopotassium salt (530.7 mg).

Embodiment 3

[0060] This example discloses the inhibitory effect of 14-O-methylandrographolide-19-O-phosphate monosodium salt (CXL-6) on the secretion of NO from macrophages induced by LPS:

[0061] 1. Drugs and instruments:

[0062] Lipopolysaccharide (LPS) and MTT were purchased from Sigma; mouse macrophage RAW 264.7 was purchased from the Cell Bank of the Chinese Academy of Sciences (ATCC); RPMI 1640 medium, penicillin, streptomycin, and fetal bovine serum were purchased from Gibco; others Commonly used biochemical reagents are all domestically produced analytically pure; automatic microplate reader (produced by Biotek Group in the United States); constant temperature CO 2 Incubator (the United States, produced by Thermo Company). Andrographolide was purchased from the market and dissolved in DMSO for in vitro cell experiments. 14-O-methylandrographolide-19-O-phosphate monosodium salt was prepared according to the method in Example 1, and Chuanhuning, Lianbizhi and Xiyanping were purc...

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Abstract

The invention discloses a new water-soluble andrographolide derivative, salt and a preparation method thereof and medical application of the derivative comprising the salt and pharmaceutical composition. The invention also discloses an inhibiting action of andrographolide derivative to macrophage secretion NO induced by LPS, antibacterial action and inhibiting action to pinna swelling induced by xylene, can be used for preparing treating drugs for anti-inflammatory, antibacterial, antivirus and anticancer and can be used for preparing drugs for treating infectious shock, septicemia, inflammatory bowel disease, rheumatoid arthritis and juvenile rheumatoid arthritis.

Description

Technical field: [0001] The invention relates to a new compound, specifically a new andrographolide derivative, including a salt of the derivative, a preparation method and a medical application thereof. Background technique: [0002] Andrographolide is a diterpenoid in Andrographis paniculata (Burm.f.) Nees, molecular formula: C 20 h 30 o 5 , is a colorless square or rectangular crystal, m.p.: 230~232℃, [α] D 20 : -126° (c=0.2, H 2 O). Very bitter taste, soluble in methanol, ethanol, propanol, pyridine, slightly soluble in chloroform, ether, hardly soluble in water and petroleum ether. The structural formula is as follows [0003] [0004] Because andrographolide is insoluble in water, it brings difficulties to the preparation of injections. At present, there are many methods to be used to convert andrographolide into various derivatives to improve the water solubility of andrographolide, and Xiyanping Injection (total sulfonate of andrographolide), Chuanhuning (...

Claims

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Application Information

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IPC IPC(8): C07F9/655A61K31/665A61P29/00A61P31/00A61P35/00C07D307/58
Inventor 刘珂李英霞邵萌
Owner SUZHOU LEINA PHARMA RES DEV
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