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Glucose derivatives of glaucocalyxin A as well as preparation method and application of glucose derivatives

A technology of glucose derivatives and blue calyxine, which is applied in the field of medical invention and can solve the problems of low bioavailability and the like

Active Publication Date: 2015-04-29
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Eleculin has strong anti-tumor effect in vitro, but it takes a long time to produce drug effect in vivo [Zhang Chong, Shang Xiaojun, Ma Suying, Bai Suping. Medicine Herald, 2013, 32, 1399-1402], Biology low utilization

Method used

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  • Glucose derivatives of glaucocalyxin A as well as preparation method and application of glucose derivatives
  • Glucose derivatives of glaucocalyxin A as well as preparation method and application of glucose derivatives
  • Glucose derivatives of glaucocalyxin A as well as preparation method and application of glucose derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1: the preparation of the cyanine A glucose derivative Ia, Ib, Ic containing triazole group

[0073] The reaction formula is as follows:

[0074]

[0075] 1.1: Preparation of fully acetylated glucose

[0076] Weigh 8.287g of anhydrous sodium acetate and place it in a crucible, adjust the temperature so that it loses all the water, transfer it to a mortar immediately after cooling, add dry glucose (10.636g, 590mmol), mix well and transfer it to 250mL Add 150 mL of acetic anhydride to the round bottom flask, adjust the temperature to 100°C, and react for 2-3 hours. After cooling to room temperature, the reaction solution was poured into ice water, and a white solid precipitated out. After suction filtration, it was washed with 5 times the amount of distilled water to obtain peracetylated glucose. After drying, 17.707 g of white solid was obtained, with a yield of 77%.

[0077] 1.2: Preparation of fully acetylated bromoglucose

[0078] Take the compound (4...

Embodiment 2

[0108] Embodiment 2: the preparation of the cerulein derivative IIa of glucose sugar ester

[0109] The reaction formula is as follows:

[0110]

[0111] 2.1: Preparation of 2-(4-formyl-2-methoxy-phenoxy)-acetic acid

[0112] Take chloroacetic acid (4.822g, 51.3mmol) and add an appropriate amount of saturated potassium carbonate solution to adjust the pH value of the solution to 9 to dissolve all the samples, and transfer it to a constant pressure dropping funnel for later use. Take 3-methoxy-4-hydroxybenzaldehyde (5.198g, 34.2mmol) in a 250mL bottom flask, add an appropriate amount of 5% sodium hydroxide solution to adjust the pH value to about 9, stir to dissolve all the samples, adjust the constant pressure drop Liquid funnel, transfer all the samples to the round bottom flask within 30min, then add 321mg of potassium iodide, reflux at 110°C for 5h, cool to room temperature, adjust the pH value of the solution to 1 with concentrated hydrochloric acid, precipitate out, f...

Embodiment 3

[0118] Embodiment 3: the preparation of the cerulein derivatives IIb and IIc of glucoside

[0119] The reaction formula is as follows:

[0120]

[0121] 3.1: Preparation of peracetylated glucosides substituted by benzaldehyde

[0122] 3.1.1: Take the fully acetylated bromoglucose (2.498g, 6.09mmol) and 3-methoxy-4-hydroxybenzaldehyde (0.926g, 6.09mmol) obtained in 1.2 of Example 1 in a 100mL round bottom flask , add 25mL of dichloromethane to dissolve all the samples, then add TBAB (1.961g, 6.09mmol) and 20mL of saturated potassium carbonate solution, react at 60°C for 5h, cool to room temperature, transfer the reaction solution into a separatory funnel, add Dichloromethane 50mL, washed with distilled water 50mL×3, saturated ammonium chloride 50mL×3, saturated brine, anhydrous MgSO 4 Drying, filtration, concentration under reduced pressure, separation and purification by column chromatography, eluting with petroleum ether / ethyl acetate 3:1, gave 1.758 g of white powdery s...

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PUM

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Abstract

The invention relates to glucose derivatives of glaucocalyxin A. The glucose derivatives have a structure represented by a formula I or a formula II, wherein R1 represents hydrogen or methoxyl, R2 represents hydrogen or acetyl, and n represents 0 or 1. The invention further relates to a preparation method and application of the glucose derivatives. By virtue of a cytotoxic activity evaluation experiment, a result shows that the glucose derivatives of glaucocalyxin A have relatively strong inhibitory activity for human tumor cell proliferation, and the activity is superior to that of a parent compound, namely glaucocalyxin A. (The formula is shown in the description).

Description

technical field [0001] The invention relates to the field of medical inventions, in particular to a glucose derivative of glaucocalyxin A (GLA), a preparation method and application thereof. Background technique [0002] Glaucocalyxin A (GLA), chemical name: (5β,7α,9β,10α)-7,14-dihydroxykauri-16-ene-3,15-dione; also known as leukamenin F, Molecular formula is C20H28O4, molecular weight: 332.43, CAS registration number: 79498-31-0, density: 1.22g / cm 3 , melting point: 513.4°C, easily soluble in methanol and ethanol, and its structural formula is shown in formula III. [0003] [0004] Isocalyxin is the main medicinal ingredient of Isodon japonica var. glaucocalyx, a plant of the genus Isodon japonica var. glaucocalyx. In 1981, Xu Yunlong et al. Research. 1981, 3(03): 1-3) firstly obtained cyanine A, which is a kind of tetracyclic diterpene compound with enantio-kaurane skeleton, which is isolated from S. The content in the dry leaves of Calyx japonica is as high as 1.03...

Claims

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Application Information

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IPC IPC(8): C07H19/056C07H13/04C07H15/26C07H1/00A61K31/7056A61K31/7048A61P35/00A61P35/02
CPCC07H1/00C07H13/04C07H15/26C07H19/056
Inventor 白素平李婷尹志奎黄锋刘兆敏海广范陈亮辉任茜茜周慧超张荒荒
Owner XINXIANG MEDICAL UNIV
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