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4', 5-dyhydroxyl-7-(4-(N, N-diethylamino group) butoxy) isoflavone, preparation method and application of 4', 5-dyhydroxyl-7-(4-(N, N-diethylamino group) butoxy) isoflavone

A technology of diethylamino and isoflavones, which can be used in pharmaceutical formulations, medical preparations containing active ingredients, organic active ingredients, etc., and can solve problems such as application limitations and lack of acetylcholinesterase inhibitory activity.

Inactive Publication Date: 2011-07-20
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this compound does not have acetylcholinesterase inhibitory activity, its application is subject to certain restrictions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: 4′, 5-dihydroxy-7-[4-(N,N-diethylamino) butoxy] isoflavone) and its preparation

[0023] The preparation of genistein derivative 4′, 5-dihydroxy-7-[4-(N,N-diethylamino) butoxyl] isoflavone comprises the following steps:

[0024] 1. Preparation of 4′,5-dihydroxy-7-(4-bromobutoxy)isoflavone

[0025] Genistein (0.27 g, 1 mmol), 1,4-dibromobutane (5.4 g, 25 mmol), K 2 CO 3 (0.07 g, 0.5 mmol) was dissolved in 60 mL of anhydrous DMF, and ultrasonically reacted at 40 °C for 1.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the insoluble matter was filtered off, and the filtrate was distilled under reduced pressure to obtain a light yellow solid, which was recrystallized in acetone to obtain a light yellow needle-like crystal with a yield of 86% and a melting point of 130-131°C.

[0026] 1 H NMR (DMSO-d 6): 1.83 (m, 2H), 1.94 (m, 2H), 3.60 (t, J = 6.2 Hz, 2H), 4.12 (t, J = 6.4 Hz, 2H), 6.40 (d, J = 2.0 Hz, 1...

Embodiment 2

[0030] Example 2: Acetylcholinesterase inhibitory activity of genistein derivative 4′,5-dihydroxy-7-[4-(N,N-diethylamino)butoxy]isoflavone

[0031] 1. 4′,5-Dihydroxy-7-[4-(N,N-diethylamino)butoxy]isoflavones inhibiting activity of acetylcholinesterase in electric eel

[0032] Enzyme reaction at 25 o C, carried out in 0.1 M phosphate buffer at pH 8.0, with a total reaction volume of 200 μL, containing 20 μL of 3.33 mM 5,5’-dithio-bi(2-nitrobenzoic acid), 0.35 U / mL acetylcholine 20 μL of esterase solution and 20 μL of 5.3 mM thioacetylcholine iodide solution, 10 μL of the test compound solution, and detected with a microplate reader (Sunrise, Tecan, Austria) at 412 nm for 5 min. Samples were repeated three times. Taking the optical density value of wells without compound as 100%, compare the optical density of wells for compound measurement with it, and the percentage decrease is the enzyme inhibition rate. Measure the inhibitory activity of the compound on at least 5 concen...

Embodiment 3

[0038] Example 3: Estrogenic activity of genistein derivative 4′,5-dihydroxy-7-[4-(N,N-diethylamino)butoxy]isoflavone

[0039] Effect of 1, 4′,5-dihydroxy-7-[4-(N,N-diethylamino)butoxy]isoflavone on promoting the proliferation of estrogen-dependent MCF-7 cells

[0040] MCF-7 cells at 1.5×10 4 Concentrations were seeded in 96-well plates. After the cells were cultured for 24 h to adhere to the wall, the original medium was sucked off, and the 1640 medium containing 5% activated carbon / dextran-treated fetal bovine serum was replaced. Continue culturing for 48 h to deplete the estrogen in the cells. The experiment was divided into blank control group, drug treatment group and positive control group. The blank group was replaced with 1640 medium containing 5% activated carbon / dextran-treated fetal bovine serum; the drug-treated group was replaced with 100 μM, 50 μM, 10 μM, 1 μM, 0.1 μM, 0.01 μM, 0.001 μM, 0.0001 μM and 0.00001 μM 4′,5-dihydroxy-7-[4-(N,N-diethylamino)butoxy]is...

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Abstract

The invention discloses 4', 5-dyhydroxyl-7-(4-(N, N-diethylamino group) butoxy) isoflavone of dye lignin derivative, a preparation method and an application of the 4', 5-dyhydroxyl-7-(4-(N, N-diethylamino group) butoxy) isoflavone. The 4', 5-dyhydroxyl-7-(4-(N, N-diethylamino group) butoxy) isoflavone obtained by chemically modifying the dye lignin derivative has the acetylcholinesterase inhibition activity, the estrogen activity and the nerve cell protective action; and the 4', 5-dyhydroxyl-7-(4-(N, N-diethylamino group) butoxy) isoflavone which is taken as a multi-function target spot can be used for preparing the alzheimer disease-resistant medicament.

Description

technical field [0001] The invention relates to a genistein derivative and its preparation method and application, in particular to 4',5-dihydroxy-7-[4-(N,N-diethylamino)butoxy]isoflavone And its preparation method and application. Background technique [0002] Alzheimer's disease is a common senile brain neurodegenerative disease with a high incidence, and has become one of the diseases that seriously threaten the life and health of the elderly in modern society. Typical pathological changes of the disease include β Amyloid deposits form senile plaques, neurofibrillary tangles, basal forebrain cholinergic dysfunction and extensive neuronal loss and altered synaptic morphology in the cortex and hippocampus (see: Roberson ED, Mucke L. 100 years and counting: prospects for defeating Alzheimer's disease. Science 2006;314(5800):781-4). [0003] The study found that the lesions of the cortex and hippocampus in patients with Alzheimer's disease were more obvious, and the cholin...

Claims

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Application Information

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IPC IPC(8): C07D311/36A61K31/352A61P25/28
CPCC07D311/36A61K31/352A61P25/28
Inventor 谭仁祥史大华吴俊华宴志强张丽娜王玉蓉
Owner NANJING UNIV
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