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Medical use of triacetyl andrographolide as proinflammatory cytokine inhibitor

An inflammatory cytokine and andrographolide technology is applied in the field of medical use of triacetylandrographolide as an inflammatory cytokine inhibitor, and can solve the problem that the inhibitory effect and activity of triacetylandrographolide cannot be predicted. How to wait for the problem to achieve the effect of improving the inhibitory activity

Active Publication Date: 2009-02-25
SUZHOU LEINA PHARMA RES DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In summary, it can be seen that even if all the above-mentioned published contents about andrographolide and triacetylandrographolide are combined, it is impossible to speculate whether triacetylandrographolide has an inhibitory effect on inflammatory cytokines and how active it is

Method used

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  • Medical use of triacetyl andrographolide as proinflammatory cytokine inhibitor
  • Medical use of triacetyl andrographolide as proinflammatory cytokine inhibitor
  • Medical use of triacetyl andrographolide as proinflammatory cytokine inhibitor

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0028] Preparation Example 1 Preparation of Andrographolide

[0029] Take 20 g of the crude product of andrographolide, dissolve it in 450 mL of methanol at 72° C., let it stand for 24 hours to obtain white crystals, and then dry them to obtain andrographolide.

preparation example 2

[0030] Preparation Example 2 Preparation of Triacetylandrographolide

[0031] 1g andrographolide dissolved in 10mLAc 2 O, heated to reflux for 2 hours, the reaction mixture was extracted with ethyl acetate, the organic layer was successively water, saturated NaHCO 3 and saturated brine, anhydrous MgSO 4 dry. Triacetylandrographolide was obtained as a white solid by silica gel column chromatography. The molecular formula is: C 26 h 36 o 8 .

[0032] Compound confirmation data are as follows:

[0033] (cm -1 ): 3454, 3080, 2954, 1731, 1683, 1375, 1250, 1191, 1075, 1026, 895, 606.

[0034] 1 H (400MHz, CDCl 3 ):δ

[0035] 7.00 (td, J=6.84, 1.48Hz, 1H, H-12), 5.92 (d, J=5.96Hz, 1H, H-14), 4.90 (bs, 1H, H-17a), 4.60 (dd, J =11.68, 4.26Hz, 1H, H-15a), 4.55(dd, J=11.24, 6.08Hz, 1H, H-15b), 4.53(bs, 1H, H-17b), 4.36(d, J=11.80Hz , 1H, H-19a), 4.25(dd, J=11.24, 1.80Hz, 1H, H-3), 4.12(d, J=11.80Hz, 1H, H-19b), 2.52~2.37(m, 3H) , 2.12(s, 3H), 2.05(s, 6H), 2.00~1.96(m, 1H...

preparation example 3

[0039] Preparation Example 3 Preparation of 3,19-diacetylandrographolide, 14-acetylandrographolide, and 14,19-diacetylandrographolide

[0040] 5g of andrographolide was added to 30mL of acetic acid, stirred and heated to 80°C, and reacted overnight. Extracted with ethyl acetate, the organic layer was washed with water and saturated brine successively, anhydrous MgSO 4 dry. 3,19-diacetylandrographolide (AP11), 14,19-diacetylandrographolide (AP12), and 14-acetylandrographolide (AP13) were obtained by column chromatography.

[0041]

[0042] The confirmed data of AP11 compound are as follows:

[0043] Molecular formula: C 24 h 34 o 7 (434)

[0044] 1 H (400MHz, CDCl 3 ): 6.97 (1H, m, H-12), 5.03 (1H, d, J=5.6Hz, H-14), 4.92 (1H, s, H-17), 4.62 (1H, s, H-17) , 4.59 (1H, dd, J=11.2, 4.8Hz, H-3), 4.47 (1H, dd, J=10.4, 6.0Hz, H-15), 4.38 (1H, d, J=11.6Hz, H- 19), 4.26 (1H, dd, J=10.4, 2.0Hz, H-15), 4.11 (1H, d, J=12.0Hz, H-19), 2.05 (6H, s, CH 3 CO-), 1.04 (3H, s, H-18)...

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Abstract

The invention relates to an application of 3,14,9-acetyl andrographolide in the preparation of an proinflammatory cytokine, wherein, the proinflammatory cytokine comprises any one of TNF-Alpha, IL-1Alpha, IL-1Beta, IL-2, IL-4, IL-6, IL-8, IL-10, IFN-Gamma and NO.

Description

technical field [0001] The invention relates to the application of triacetylandrographolide in the preparation of inflammatory cytokine inhibitors. Background technique [0002] Inflammatory cytokines are mainly secreted by macrophages, including TNF-α, IL-1α, IL-1β, IL-2, IL-4, IL-6, IL-8, IL-10, IFN-γ and other pro-inflammatory cytokines Cytokines and nitric oxide (NO) with the characteristics of inflammatory factors, etc. The most studied ones are TNF-α, IL-1β, IL-6, and NO. Excessive secretion of inflammatory cytokines plays an important role in the occurrence and development of many diseases. Such as: systemic inflammatory response syndrome (SIRS), sepsis, septic shock, septic shock, multiple organ dysfunction syndrome, rheumatoid arthritis, osteoarthritis, spondyloarthropathy, rheumatoid arthritis Inflammation, hypertension, coronary heart disease, myocardial infarction, heart failure, diabetes, systemic lupus erythematosus, lupus nephritis, scleroderma, sarcoidosis...

Claims

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Application Information

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IPC IPC(8): A61K31/365A61P29/00A61P31/00A61P25/00A61P35/00A61P11/00
Inventor 刘珂邵萌赵烽关玉昆滕厚雷吴巍徐卉翟大伟韩飞冯妍
Owner SUZHOU LEINA PHARMA RES DEV
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