Novel estrogen analogue as well as preparation method and application thereof

An estrogen and analog technology, applied in the field of new estrogen analogs, can solve the problem of not involving specific drug molecules for the treatment of azoospermia, and achieve the effect of good drug effect

Inactive Publication Date: 2021-08-27
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the design and synthesis of estrogen analogues has become a research hotspot for scientists, especially for pharmacologists, but so far there is still no drug molecule that can specifically treat azoospermia

Method used

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  • Novel estrogen analogue as well as preparation method and application thereof
  • Novel estrogen analogue as well as preparation method and application thereof
  • Novel estrogen analogue as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0034] The preparation steps of the novel estrogen analogs are as follows: Add the weighed arylamine compound 1, substituted acetylene 2 and metal catalyst M m x n , add the corresponding solvent, in the air atmosphere, stir the reaction at a temperature of 60-120°C for 1h-48h, cool to room temperature, add ethyl acetate to dilute, wash with saturated brine, dry the organic phase with anhydrous magnesium sulfate, column layer Analysis and isolation of estrogen analogue 3.

[0035] Wherein, the arylamine compound 1 is selected from one of the following:

[0036]

Embodiment 1

[0039] Synthesis of N-benzyl-4-methoxy-2-(1-phenylvinyl)aniline:

[0040]

[0041] Add raw material 1a (0.20mmol), MnI 2 (0.04mmol), 2h (0.4mmol) and toluene (2.0mL), stirred at 100°C for 24h, cooled to room temperature, diluted with ethyl acetate (5mL), washed with saturated brine (5mL), and the organic phase was washed with anhydrous Dried over magnesium sulfate, spin-dried and then column chromatographed with eluent (ethyl acetate:n-hexane=1:100), the product 3h was obtained as 40 mg of white solid, with a yield of 63%. 1 H NMR (400MHz, CDCl 3 ): δ7.39–7.28(m,5H), 7.23–7.17(m,3H), 7.05–7.01(m,2H), 6.80–6.76(m,2H), 6.58(d,J=8.4Hz,1H ), 5.79(d, J=1.2Hz, 1H), 5.36(d, J=1.2Hz, 1H), 4.16(s, 2H), 3.77(s, 1H), 3.74(s, 3H); 13 C NMR (100MHz, CDCl 3 ): δ151.6, 147.0, 139.6, 139.6, 139.6, 128.7, 128.6, 128.4, 128.2, 127.2, 126.9, 126.7, 116.8, 116.5, 114.1, 112.2, 55.8, 48.9.

Embodiment 2

[0043] Synthesis of N-benzyl-2-(1-(2-fluorophenyl)vinyl)-4-methoxyaniline:

[0044]

[0045] Add raw material 1a (0.20mmol), MnCl 2 (0.02mmol), 2i (0.4mmol) and toluene (2.0mL), stirred at 100°C for 24h, cooled to room temperature, diluted with ethyl acetate (5mL), washed with saturated brine (5mL), and the organic phase was washed with anhydrous Dried over magnesium sulfate, spin-dried and then column chromatographed with eluent (ethyl acetate:n-hexane=1:100), the product 3i was obtained as 48 mg of white solid, with a yield of 72%. 1 H NMR (400MHz, CDCl 3 ): δ7.30–7.02(m,9H), 6.79–6.71(m,2H), 6.56(d,J=8.8Hz,1H), 5.87(t,J=1.2Hz,1H), 5.63(t, J=1.2Hz, 1H), 4.21(s, 2H), 3.94(s, 1H), 3.73(s, 3H); 13 C NMR (100MHz, CDCl 3): δ161.7, 159.2, 151.5, 141.4, 139.6, 139.3, 130.5(d, JC-F=3.1Hz), 129.3(d, JC-F=8.4Hz), 129.0, 128.5, 127.1, 127.0, 124.1(d, JC-F=3.7Hz), 121.4(d, JC-F=6.9Hz), 116.4, 116.3, 116.0, 113.9, 112.2, 55.8, 48.9; HRMS(ESI) m / z Calcd for C 22 h 20 FNO[M+H] +...

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PUM

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Abstract

The invention provides a novel estrogen analogue as well as a preparation method and application thereof, and the preparation method comprises the following steps: sequentially adding weighed arylamine compounds, substituted acetylene and a metal catalyst MmXn into a reaction flask, adding a corresponding solvent, reacting in an air atmosphere at the temperature of 60-120 DEG C, stirring for 1-48 hours, cooling to room temperature, adding ethyl acetate for dilution, washing with a saturated saline solution, drying an organic phase with anhydrous magnesium sulfate, and carrying out column chromatography separation to obtain the estrogen analogue. The estrogen analogue is efficiently and rapidly synthesized by adopting a cheap metal catalysis technology; the novel estrogen analogue has an obvious spermatogenesis promoting effect on azoospermia rats, and has the potential of being developed into a specific azoospermia treatment medicine.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and specifically relates to a novel estrogen analogue, a preparation method and application thereof. Background technique [0002] In recent years, the infertility rate caused by factors such as food safety, environmental pollution, drug side effects and increased life pressure has increased year by year. According to the report of the World Health Organization, the incidence of infertility among couples of normal childbearing age is nearly 15%, and the male factor accounts for about 50%, and the proportion shows an increasing trend year by year. According to statistics, the quality of human semen has declined significantly over the past half century, and the density of sperm has dropped by half. Among them, the quality of semen in my country has decreased by 1% every year. As the quantity and quality of human sperm decrease year by year, the proportion of male infertility will become higher...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/84C07C213/08A61P15/08
CPCC07C217/84A61P15/08
Inventor 孙斐杨锦飞吴小龙林登峰
Owner NANTONG UNIVERSITY
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