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Application of genistein derivative in preparing medicament for treating learning and memory disorder

A technology for learning and memory impairment and genistein, which is applied in the field of chemical pharmaceuticals to achieve the effect of simple process, good curative effect, and improvement of learning and memory

Inactive Publication Date: 2012-09-12
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

4',5'-dihydroxy-7-[4-(N,N-diethylamino)butoxy]isoflavone has a stronger binding force to ER β, which can better improve learning and memory and reduce adverse reactions. There is no such structure reported in the drugs for improving learning and memory at present

Method used

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  • Application of genistein derivative in preparing medicament for treating learning and memory disorder
  • Application of genistein derivative in preparing medicament for treating learning and memory disorder
  • Application of genistein derivative in preparing medicament for treating learning and memory disorder

Examples

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Embodiment 1

[0012] Example 1: 4',5'-dihydroxy-7-[4-(N,N-diethylamino)butoxy]isoflavone and its preparation

[0013] The preparation of genistein derivative 4',5'-dihydroxy-7-[4-(N,N-diethylamino)butoxy]isoflavone comprises the following steps:

[0014] ① Preparation of 4',5'-dihydroxy-7-[4-(N,N-diethylamino)butoxy]isoflavone

[0015] Genistein (0.27g, 1mmol), 1,4-dibromobutane (5.4g, 25mmol), K2CO3 (0.07g, 0.5mmol) were dissolved in 60ml of anhydrous DMF, and ultrasonically reacted at 40°C for 1.5h. After the reaction was complete, the mixture was cooled to room temperature. After filtering off the insoluble matter, 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.

[0016] 1 H NMR (DMSO-d 6 ):1.83 (m, 2H), 1.94 (m, 2H), 3.60 (t, J=6.2Hz, 2H), 4.12 (t, J=6.4Hz, 2H), 6.40 (d, J=2.0Hz, 1H ), 6.65 (d, J=2.0Hz, 1H), 6.80 (d...

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Abstract

The invention belongs to the field of chemical pharmaceutical technology, and in particular relates to application of a genistein derivative 4', 5'-dyhydroxy-7-[4-(N, N-diethylamino) butoxy] isoflavone in preparing a medicament for treating learning and memory disorder. 4', 5'-dyhydroxy-7-[4-(N, N-diethylamino) butoxy] isoflavone has the effect of promoting macrophage chemotactic fator (MCF)-7 cell proliferation and the action effect is in a bell jar type. The latent time of female castrated mice (oophorectomy is performed) in a water maze experiment is shortened and the error time of the mice is greatly decreased in a Y maze experiment. The fact indicates that 4', 5'-dyhydroxy-7-[4-(N, N-diethylamino) butoxy] isoflavone can effectively improve learning and memory capability. The improvement of learning and memory is consistent with the enhancement of phosphorylation of calcium-calmodulin dependent protein kinase (CaMk) II. 4', 5'-dyhydroxy-7-[4-(N, N-diethylamino) butoxy] isoflavone has good effects of improving learning and memory and can be used for preparing the medicament for improving learning and memory.

Description

1. Technical field [0001] The invention belongs to the technical field of chemical pharmacy, and specifically relates to the preparation and treatment of learning and memory disorders by 4',5'-dihydroxy-7-[4-(N,N-diethylamino)butoxy]isoflavone, a genistein derivative application in medicine. 2. Background technology [0002] With the aging of the population and the increase of mental pressure, learning cognitive impairment has become a serious social problem. Estrogen and phytoestrogens have outstanding effects in improving learning and memory (Barbara BS.Estrogen and cognitive aging in women.TRENDS in Pharmacological Sciences.2002;23(11):527-534.;Craig MC and Murphy DG.Oestrogen, Cognition and the Maturing Female Brain. Journal of Neuroendocrinology 2006;19:1-6). In addition to menopausal and perimenopausal women, some people have given small doses of estrogen to male patients with memory impairment, and successfully improved their learning and memory functions (Sex stero...

Claims

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Application Information

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IPC IPC(8): C07D311/36A61K31/352A61P25/28
Inventor 谭仁祥杜荣辉张爱华王婷
Owner NANJING UNIV
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