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Scutellarein aglycone prodrug and preparation method thereof

A technology of baicalein aglycone and scutellarin is applied in the field of scutellarin aglycone prodrug and its preparation, and achieves the effects of mild reaction conditions, simple operation and easy-to-obtain raw materials

Inactive Publication Date: 2013-05-22
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no report of scutellarein aglycone prodrug with cyclodextrin as carrier

Method used

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  • Scutellarein aglycone prodrug and preparation method thereof
  • Scutellarein aglycone prodrug and preparation method thereof
  • Scutellarein aglycone prodrug and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: The preparation of mono(6-amino-6-deoxy)-β-cyclodextrin bonded scutellarein prodrug is as follows:

[0046] Add 0.25 g (0.87 mmol) of scutellarein aglycone, 64 mL (0.87 mmol) of 37% formaldehyde solution, and 0.986 g (0.87 mmol), anhydrous N,N-dimethylformamide 15mL and catalytic amount 0.87mL (0.0087mmol) concentrated hydrochloric acid, stir evenly, under the protection of inert gas nitrogen, heat up to 50°C, react for 10h, after the reaction, 60 The reaction solution was evaporated to dryness under reduced pressure at ℃, the residue was fully dissolved in 3 mL of water, filtered, 300 mL of acetone was added dropwise to the filtrate, filtered, the precipitate was collected, and vacuum-dried at 50 °C for 24 hours to obtain 6-scutellarein bonded The crude product of β-cyclodextrin, the yield is 1.095g, and the yield is 88%. It is purified and refined by LH-20 gel column, washed with water and methanol-water, and the same components are combined to obtain mon...

Embodiment 2

[0048] Example 2: The preparation of mono(6-ethylenediamino-6-deoxy)-α-cyclodextrin bonded scutellarein prodrug is as follows:

[0049] Add 0.25g (0.87mmol) of scutellarein aglycone, 78mg (2.51mmol) of paraformaldehyde, and 2.046g (1.74 mmol), 15 mL of anhydrous dimethyl sulfoxide, and a catalytic amount of 1.13 mg (0.0087 mmol) of boron trifluoride diethyl ether, stirred evenly, under the protection of inert gas argon, heated to 25 ° C, and reacted for 48 h. After the reaction, 60 The reaction solution was evaporated to dryness under reduced pressure at ℃, the residue was fully dissolved in 3 mL of water, filtered, 300 mL of acetone was added dropwise to the filtrate, filtered, the precipitate was collected, and vacuum-dried at 50 °C for 24 hours to obtain 6-scutellarein bonded β-cyclodextrin crude product, the yield is 1.072g, the yield is 84%. Purify and refine with LH-20 gel column, wash with water and methanol-water, combine the same components to obtain mono(6-ethylen...

Embodiment 3

[0050] Example 3: The preparation of mono(6-diethylenediamino-6-deoxy)-γ-cyclodextrin bonded scutellarein aglycone prodrug is as follows:

[0051] Add 0.25g (0.87mmol) of scutellarein aglycone, 52mg (1.74mmol) of paraformaldehyde, and 3.183g of mono(6-diethylenediamine-6-deoxy)-γ-cyclodextrin into the reaction flask in sequence ( 2.51mmol), water 15mL and catalyst 1.74mL (0.0174mmol) concentrated hydrochloric acid, stir evenly, under the protection of inert gas argon, heat up to 75°C, react for 24h, after the reaction, evaporate the reaction solution under reduced pressure at 60°C, The residue was fully dissolved in 3 mL of water, filtered, 300 mL of acetone was added dropwise to the filtrate, filtered, the precipitate was collected, and vacuum-dried at 50°C for 24 hours to obtain the crude product of 6-scutellarein bonded β-cyclodextrin with a yield of 1.127g, the yield is 85%. Purify and refine with LH-20 gel column, wash with water and methanol-water, combine the same co...

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Abstract

The invention relates to the field of drug synthesis, and discloses a scutellarein aglycone prodrug and a preparation method thereof. The scutellarein aglycone prodrug takes cyclodextrin as a carrier, and a scutellarein aglycone molecule, a modified amino of an arbitrary hydroxyl of the cyclodextrin and a formaldehyde reagent commonly generate trimolecular reaction (Manich reaction) through an activated hydrogen on a C8 location of the scutellarein aglycone molecule so as to prepare the scutellarein aglycone prodrug. Compared with scutellarein aglycone, the scutellarein aglycone prodrug has more hydrophilic active groups, good biocompatibility, better water solubility and high bioavailability; and on the other hand, the preparation method of the scutellarein aglycone prodrug has the advantages of simplicity in operation, easily-obtained raw materials and moderate reaction conditions, and can be used for preparing the scutellarein aglycone prodrug in a large scale.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a scutellarein aglycone prodrug and a preparation method thereof. Background technique [0002] Scutellarein, also known as scutellarein (scutellarein, MW=286.047), its chemical structure is 5,6,7,4'-tetrahydroxyflavone, and the difference from scutellarin is at the 7th position free hydroxyl. [0003] Scutellaria scutellarin is from the Chinese medicinal plant Compositae Erigerin breviscapus (Vant.) The flavonoids extracted from Hand.-Mazz., among which scutellarin (Scutellarin, SCU), as a flavone glycoside, is the main active ingredient in the extract. Scutellarin has the effects of dilating blood vessels, increasing arterial flow, reducing blood viscosity, reducing peripheral resistance, reducing platelet count and inhibiting platelet aggregation. Therefore, scutellarin preparations (tablets or injections) are mainly used in the clinical treatment of coronary heart disease, a...

Claims

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Application Information

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IPC IPC(8): C08B37/16A61K47/48A61K47/61
Inventor 杨波易东廖霞俐赵榆林高传柱杨健
Owner KUNMING UNIV OF SCI & TECH
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