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Formononetin derivative as well as preparation method and application thereof

A technology of formononetin and its derivatives, applied in drug combination, bone disease, organic chemistry, etc.

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

AI Technical Summary

Problems solved by technology

At present, the application of phytoestrogens-based compounds in osteoporosis drugs is less, based on existing drugs, the discovery of new compounds is of great significance for the diagnosis and treatment of osteoporosis

Method used

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  • Formononetin derivative as well as preparation method and application thereof
  • Formononetin derivative as well as preparation method and application thereof
  • Formononetin derivative as well as preparation method and application thereof

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preparation example Construction

[0065] When the formononetin derivative has the structure shown in formula I, the preparation method comprises the following steps:

[0066] 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;

[0067]

[0068] R in said formula a 1 , R 2 The groups are the same as in formula I.

[0069] 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 a-2).

[0070]

[0071] In the present invention, the first amino compound is specifically according to R 3 The type of group...

Embodiment 1

[0103] Embodiment 1: Preparation of F1

[0104] 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 to obtain a brownish-yellow precipitate, collected the brownish-yellow precipitate to obtain a crude product, separated by silica gel column chromatography, and the reagents used were petroleum ether-ethyl acetate, petroleum ether and acetic acid The volume ratio of ethyl ester is 2:1, R f 0.11, the product F163.5 mg was obtained, and the yield was 47.31%.

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

[0106] 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).

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

Embodiment 2

[0110] Embodiment 2: the preparation of F2

[0111] 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%.

[0112] The H NMR spectrum, carbon spectrum and mass spectrum data of the product are:

[0113] 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).

[0114] 13 C-NMR (400MHz, DMSO-D6) ...

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Abstract

The invention relates to the technical field of medicine synthesis, and provides a formononetin derivative as well as a preparation method and application thereof. The invention provides the derivative taking formononetin as a mother nucleus based on natural plant estrogen with anti-osteoporosis activity. The derivative has inhibitory activity on osteoclasts, can promote bone marrow mesenchymal stem cells to be differentiated into osteoblasts, and activates the bone forming ability of the osteoblasts; the expression of osteoblast related genes can be promoted, so that the balance of osteoclast and osteogenesis is improved; the level of bone mineral density in individuals with abnormal bone mineral density can be increased, the bone volume fraction in individuals with abnormal bone volume fraction can be increased, and the ratio of bone surface area to bone volume in individuals with abnormal ratio of bone surface area to bone volume can be adjusted; and the derivative has a wide application prospect in preparation of medicines for preventing or treating diseases or symptoms caused by osteoblast abnormality.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a formononetin derivative and its preparation method and application. Background technique [0002] Osteoporosis (osteoporosis) is a systemic bone disease in which bone density and bone quality decrease due to various reasons, bone microstructure is destroyed, bone fragility increases, and fractures are prone to occur. Osteoporosis is divided into primary and secondary two categories. Primary osteoporosis is more common in the elderly and postmenopausal women. The etiology of idiopathic osteoporosis is still unknown. Secondary osteoporosis is caused by other diseases or drugs. Normal bone metabolism is in the balance of bone formation (osteoblast) and bone loss (osteoclast). The two complement and cooperate and play an important role in the development and formation of bones. Aging, estrogen reduction and drug interference lead to decreased activity of osteoblasts and in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36C07D405/04C07D407/04C07D498/04A61P19/10
CPCC07D311/36C07D405/04C07D407/04C07D498/04A61P19/10
Inventor 罗晓东王兆杰赵云丽闫晓君代智何英杰
Owner YUNNAN UNIV
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