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16alpha-methyl-3-hydroxyl-19-norpregnane-1, 3, 5-triene-20-ketone and preparation method thereof

A technology of norpregnantine and methyl group is applied in the field of organic compounds and their preparation, can solve the problems of low reaction yield, high price of estrone, harsh reaction conditions and the like, and achieves good stereoselectivity, high yield, Inexpensive effect

Inactive Publication Date: 2009-09-23
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are relatively few literature reports on the introduction of a methyl group at the 16-position of estrogen compounds. Only Burn et al. used 17-cyanoestrol methyl ether or 16α, 17α-methyleneestrol methyl ether as raw materials, After multi-step reaction with Grignard reagent (Burn D., Petrow V., J Chem Soc., 1962, 364), or after metal lithium-liquid ammonia reduction and Jones reagent oxidation (Burn D., Davies M.T., Petrow V., Steroids, 1964, 3(5), 583) to obtain 16α-methylestrol ether compound
The raw materials used in the two pathways need to be obtained through multi-step synthesis of estrone compounds such as estrone, and the price of estrone is relatively high, and the reaction yield with Grignard reagent in the methylation process of method one low, while the second method utilizes cyclopropane reduction and reoxidation method, the reaction conditions are harsh, and the oxidant that is not conducive to the environment is used

Method used

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  • 16alpha-methyl-3-hydroxyl-19-norpregnane-1, 3, 5-triene-20-ketone and preparation method thereof
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  • 16alpha-methyl-3-hydroxyl-19-norpregnane-1, 3, 5-triene-20-ketone and preparation method thereof

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Embodiment

[0020] Example: Method for preparing 16α-methyl-3-hydroxy-19-norpregna-1,3,5-trien-20-one

[0021] The first step of methylation

[0022] Under the protection of nitrogen, put 35.6g 3-acetoxy-pregn-5,16-dien-20-one, 1g cuprous bromide, 42.2g trimethylaluminum solution and 13g trimethylchlorosilane into 200g dry in tetrahydrofuran and stirred at room temperature for 2 hours. Add 50g of water and stir until no bubbles come out. Another 100 g of water was added. Extract twice with 180 g of dichloromethane, combine the organic phases, wash twice with 150 g of saturated brine, dry over anhydrous sodium sulfate, and filter. The filtrate was rotary evaporated to dryness and recrystallized from ethyl acetate to obtain 32.0 g of 16α-methyl-3-acetoxy-pregn-5-en-20-one with a yield of 86%. 1 HNMR (500Hz, CDCl 3 ): δ0.66(s, 3H), 0.95(d, 3H, J=6.9Hz), 1.02(s, 3H), 2.04(s, 3H), 2.12(s, 3H), 4.61(m, 1H) , 5.38(d, 1H, J=2.8Hz); 13 CNMR (100MHz, CDCl 3 ): δ209.3, 170.5, 139.6, 122.3, 7...

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Abstract

The invention relates to 16alpha-methyl-3-hydroxyl-19-norpregnane-1, 3, 5-triene-20-ketone and a preparation method thereof. In the invention, degraded product of natural diosgenine petunidin 3-acetoxyl group-pregnane-5, 16-diene-20-ketone is used as the raw material, the raw material is methylated by aluminum methide before hydrolization, 1-dehydrogenation and A aromaticcyclizationofparaflins to prepare 16alpha-methyl estrone steroid compound 16alpha-methyl-3-hydroxyl-19-norpregnane-1, 3, 5-triene-20-ketone. The compound has activity suppression effect for breast cancer cellbeads MDA-MB-231, and the preparation method is characterized by easily available raw material and high yield.

Description

technical field [0001] The invention relates to 16α-methyl-3-hydroxyl-19-norpregna-1,3,5-trien-20-one and a preparation method thereof, belonging to the technical field of organic compounds and their preparation. Background technique [0002] Estrogens have important uses in the fields of anti-osteoporosis and anti-mammary gland tumors. Therefore, it is necessary to design and synthesize new estrogens, or optimize the structure of existing estrogens, or explore environmentally friendly estrogens. Pathways are of great importance in the pharmaceutical industry. Studies have shown that the introduction of α-methyl at the 16-position of steroids can significantly improve its curative effect. For example, the most famous and arguably the most effective example is the modification of 9α-fluoro-1-dehydrocortiazole to 16α- Methyl 9α-fluoro-1-dehydrocortiazole. However, there are relatively few literature reports on the introduction of a methyl group at the 16-position of estrogen...

Claims

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Application Information

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IPC IPC(8): C07J7/00A61K31/57A61P35/00
Inventor 汤杰马皎杨帆仇文卫罗剑刘明耀王晋萍
Owner EAST CHINA NORMAL UNIV
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