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Novel scutellarin derivative as well as preparation method and pharmaceutical composition thereof

A technology of scutellarin and its derivatives, applied in the field of novel scutellarin derivatives, can solve the problem of unsatisfactory therapeutic effect, low bioavailability, dissolution of scutellarin or its derivatives To solve the problems of poor performance and achieve the effects of low cost, easy operation and mild reaction conditions

Active Publication Date: 2009-11-25
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the existing scutellarin or its derivatives have poor solubility, low bioavailability, and unsatisfactory therapeutic effects.

Method used

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  • Novel scutellarin derivative as well as preparation method and pharmaceutical composition thereof
  • Novel scutellarin derivative as well as preparation method and pharmaceutical composition thereof
  • Novel scutellarin derivative as well as preparation method and pharmaceutical composition thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0035] Preparation Example 1 Preparation of A1

[0036] 5 grams (10.8mmol) scutellarin was dissolved in 100 milliliters of DMF and dichloromethane mixed solvent, added 4.6 gram iodomethane and 7.5 grams (54mmol) potassium carbonate, stirred at room temperature for 2 days, TLC (thin layer chromatography ) shows that the reaction raw materials are complete, add 50 milliliters of 1N hydrochloric acid, and extract 3 times with 50 milliliters of ethyl acetate, combine the organic phases, dry with colorless sodium sulfate, spin the organic solvent, and use ethyl acetate / methanol as 1-10: 1 (V / V) was separated and extracted with a silica gel column to obtain 3.1 g of light yellow solid A1 with a yield of 60%. h 1 NMR (400MHz, CDCl 3 )δ7.78(d, 2H), 6.92(d, 2H), 6.60(s, 1H), 6.50(s, 1H), 4.94(d, 1H), 4.01(d, 1H), 3.83(s, 3H ), 3.81(s, 3H), 3.71(s, 3H), 3.47-3.67(m, 5H); C 13 NMR (100MHz, CDCl 3 )δ181.76,181.68,168.14,163.59,163.54,161.79,155.15,152.38,152.10,151.62,132.25,127.28,1...

preparation Embodiment 2

[0037] Preparation Example 2 Preparation of A2

[0038] 504 mg of 4', 5, 6-trimethoxyscutellarin (A1) obtained in Example 1 (dissolved in 10 milliliters of ethyl acetate and dichloromethane mixed solvent, added 0.5 milliliters of acetic anhydride and a drop of pyridine in Stir at room temperature for 6 hours, TLC detects that the reaction of the raw materials is complete, add 20 ml of saturated saline and 10 ml of ethyl acetate, extract and leave the organic phase, dry over anhydrous sodium sulfate, evaporate the solvent to dryness, and use ethyl acetate / petroleum ether by volume The ratio is 1: 1-10, and the silica gel column separation and extraction obtains 421 mg of light yellow product A2, and the yield is 66.8%. H 1 NMR (400MHz, CDCl 3)δ7.86(d, 2H), 7.03(d, 2H), 6.75(s, 1H), 6.59(s, 1H), 5.40(m, 3H), 5.26(d, 1H), 4.25(d, 1H ), 3.90(s, 3H), 3.85(s, 3H), 3.76(s, 3H), 2.11(s, 3H), 2.08(s, 3H), 2.07(s, 3H), C 13 NMR (100MHz, CDCl 3 )δ182.78,169.98,169.36,169.23,166.82,16...

experiment example 1

[0039] Experimental Example 1 Pharmacological Study on the Protective Effect of A2 on Cardiovascular and Cerebrovascular Ischemia

[0040] A large number of pharmacological studies have proved that breviscapine can dilate cerebral blood vessels, reduce cerebral vascular resistance, increase cerebral blood flow, improve microcirculation, improve blood-brain barrier permeability, enhance the phagocytic immune function of macrophages in the body, and resist pituitrin. The result is cerebral ischemia and hypoxia, and can resist platelet aggregation caused by adenosine diphosphate (ADP). Breviscapine is widely used clinically to treat paralysis caused by cerebral thrombosis, cerebral infarction and undetermined types of post-stroke paralysis, hypertension, cerebral embolism, multiple neuritis, chronic arachnoid and other cerebrovascular accidents, as well as coronary heart disease, angina pectoris, Treatment of gouty arthritis and other diseases.

[0041] The activity of compound ...

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PUM

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Abstract

The invention discloses a novel scutellarin derivative as well as a preparation method and a pharmaceutical composition thereof. The compound is prepared by the two-step reaction of methyl etherification and acetylation of the scutellarin functioning as an initial raw material and the separation and has the chemical name of 4',5,6-trimethoxy-8-(3,4,5-triacetyl-glucuronic acid)-scutellarin. The compound and the pharmaceutical composition thereof can be used for treating cardiovascular and cerebrovascular disease, phlegmasia and tumor and has the advantages of good dissolvability, high bioavailability and remarkable curative effect.

Description

technical field [0001] The present invention relates to scutellarin derivatives, in particular to a novel scutellarin derivative, a preparation method thereof, a pharmaceutical composition containing the compound, and their application in heart and cerebrovascular diseases and the like. Background technique [0002] Breviscapine is isolated and extracted from the whole plant of Breviscapus breviscapus, mainly containing scutellarin (>90%), and also contains a small amount of scutellarin (effective part). Breviscapine is also called wild scutellaria Glycosides. Breviscapine has the effects of promoting blood circulation and removing blood stasis, dispelling cold and relieving the surface, relaxing tendons and activating collaterals, expelling wind and dampness, and is often used clinically to treat cardiovascular diseases. Currently, the active ingredients of breviscapine preparations used clinically are scutellarin preparations extracted with ethanol and ethyl acetate. T...

Claims

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Application Information

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IPC IPC(8): C07H17/07A61K31/7048A61P9/00A61P29/00A61P35/00
CPCA61K9/0019C07H17/07A61K9/2054A61K9/19A61K31/7048A61K9/2018A61K47/26A61K9/0043C07H7/033A61K47/10A61K9/0056A61K9/2059A61P9/00A61P29/00A61P35/00
Inventor 朱华结金毅徐树光杨兆祥普俊学
Owner KPC PHARM INC
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