Application of formononetin derivative in preparation of medicine for treating or preventing perimenopausal syndrome

A formononetin, perimenopausal technology, applied in the field of drug synthesis to achieve the effects of increasing uterine weight, improving osteoporosis, and reducing perimenopausal syndrome

Active Publication Date: 2021-11-30
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, phytoestrogen compounds are rarely used in anti-perimenopausal syndrome drugs. Therefore, based on existing drugs, the discovery of new compounds is of great significance for the diagnosis and treatment of perimenopausal syndrome.

Method used

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  • Application of formononetin derivative in preparation of medicine for treating or preventing perimenopausal syndrome
  • Application of formononetin derivative in preparation of medicine for treating or preventing perimenopausal syndrome
  • Application of formononetin derivative in preparation of medicine for treating or preventing perimenopausal syndrome

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preparation example Construction

[0059] In the present invention, the preparation method of the formononetin derivative preferably includes the following steps:

[0060] When the formononetin derivative has the structure shown in formula I, the preparation method comprises the following steps:

[0061] The compound having the structure shown in formula a, formaldehyde and the first amino compound are mixed and reacted to obtain the compound having the structure shown in formula I; the mole of the compound having the structure shown in formula a, formaldehyde and the first amine compound The ratio is 1:1:1; the structure of the first amine compound includes primary or secondary amino groups and R 3 group;

[0062]

[0063] R in said formula a 1 , R 2 The groups are the same as in formula I.

[0064] In the present invention, the compound having the structure shown in formula a is specifically preferably formononetin (structural formula shown in formula a-1) or daidin (structural formula shown in formula...

Embodiment 1

[0096] Embodiment 1: Preparation of F1

[0097] Dissolve 134.130mg (0.5mmol) of formononetin and 70mg (0.5mmol) of hexamethylenetetramine in 6mL of glacial acetic acid, stir at room temperature until completely dissolved, heat to reflux for 6h, keep at 100°C, and quickly add 2ml of 20% hydrochloric acid, stirred for 5min, cooled to room temperature, added 10mL of water, a brownish-yellow precipitate was obtained, and the brownish-yellow precipitate was collected to obtain a crude product, which was separated by silica gel column chromatography, and the reagents used were petroleum ether-ethyl acetate, petroleum ether and ethyl acetate The volume ratio of ester is 2:1, R f 0.11, the product F163.5 mg was obtained, and the yield was 47.31%.

[0098] The H NMR spectrum, carbon spectrum and mass spectrum data of the product are:

[0099] 1 H-NMR (400MHz, DMSO-D6) δ10.48(s, 1H), 8.48(s, 1H), 8.23(d, 1H), 7.52(dd, 2H), 7.12(dd, 2H), 7.01(d , 1H), 3.88(s, 3H).

[0100] 13 C-NMR...

Embodiment 2

[0103] Embodiment 2: the preparation of F2

[0104] Formononetin 67.065mg (0.25mmol) was completely dissolved in 1mL DMSO, and the prepared mixed solution [4mL methanol, 22.5μL 36% formaldehyde (0.25mmol) and 0.042mL pyrrolidine (0.25mmol)] was slowly added dropwise, Stir at room temperature for 2 hours, reflux for 10 hours, evaporate the solvent under reduced pressure to obtain a light red solid, collect the light red solid to obtain a crude product, and separate it by silica gel column chromatography. The reagents used are petroleum ether-methanol-ethyl acetate, petroleum ether, The volume ratio of methanol and ethyl acetate is 2:1:1, R f 0.108, the product F2 was obtained with a yield of 7.25%.

[0105] The H NMR spectrum, carbon spectrum and mass spectrum data of the product are:

[0106] 1 H-NMR (400MHz, DMSO-D6) δ8.35(s, 1H), 7.91(d, 1H), 7.49(d, 2H), 7.00(d, 2H), 6.85(d, 1H), 4.11(s , 3H), 3.78(s, 2H), 2.71(m, 4H), 1.80(m, 4H).

[0107] 13 C-NMR (400MHz, DMSO-D6) ...

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Abstract

The invention relates to the technical field of medicine preparation, and provides application of a formononetin derivative in preparation of a medicine for treating or preventing perimenopausal syndrome. The formononetin derivative can regulate the in-vivo estrogen balance of an estrogen imbalance individual, relieve the perimenopausal syndrome, increase the endometrium thickness or uterus weight in a uterine atrophy individual, regulate the osteogenesis and osteoclast balance of an osteoclast abnormal individual in bone tissue, and then improve osteoporosis and other symptoms caused by the perimenopausal syndrome. Meanwhile, the formononetin derivative has the advantages of being good in stability, suitable for patent medicine, good in biological activity and low in toxicity. The formononetin derivative is applied to development of the medicine for resisting the perimenopausal syndrome or used for preparing a reagent for researching the pathological mechanism of the perimenopausal syndrome and evaluating the curative effect of the perimenopausal syndrome, and has wide application prospects.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to the application of formononetin derivatives in the preparation of drugs for treating or preventing perimenopausal syndrome. Background technique [0002] Perimenopausal syndrome (Perimenopausal syndrome) refers to women in perimenopause or after, due to the gradual decline or loss of ovarian function, autonomic dysfunction caused by the decline in estrogen levels, a series of syndromes mainly metabolic disorders. When a woman enters menopause, the level of estrogen in the body drops significantly, which leads to imbalances in the nervous, mental, psychological, endocrine and metabolic systems, and perimenopausal syndrome, which is specifically manifested as hot flashes, insomnia, irritability, osteoporosis, Endometrial atrophy, cardiovascular and cerebrovascular diseases, metabolic syndrome, breast cancer and endometrial cancer, etc. [0003] Medical research has found th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/5365A61K31/352A61K31/4025A61K31/4433A61K31/496C07D498/04C07D311/36C07D405/06C07D407/12C07D405/12A61P15/12A61P15/00
CPCA61K31/5365A61K31/352A61K31/4025A61K31/4433A61K31/496C07D498/04C07D311/36C07D405/06C07D407/12C07D405/12A61P15/12A61P15/00
Inventor 罗晓东赵云丽王兆杰闫晓君代智何英杰
Owner YUNNAN UNIV
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