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Method for preparing guggulsterone

A technology of ancient stesterone and ancient stesterone, which is applied in the field of organic chemical synthesis/pharmaceutical synthesis, can solve the problems such as yield discount of E-gusterone, and achieve the effect of high yield and short steps

Active Publication Date: 2022-01-28
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the yield of E-goldosterone is greatly reduced

Method used

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  • Method for preparing guggulsterone
  • Method for preparing guggulsterone
  • Method for preparing guggulsterone

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preparation example Construction

[0018] In a specific embodiment, the preparation method of gugusterone includes the following four steps. In the first step, the compound shown in formula 4 is generated from the compound shown in formula 3 (3-position etherification protection step); Step 2, the compound shown in Formula 5 is generated from the compound shown in Formula 4 (the 17-position side chain construction step); the 3rd step, the compound shown in Formula 6 is generated from the compound shown in Formula 5 (3-position deprotection step); and finally The important fourth step is to generate the compound shown in Formula 1 from the compound shown in Formula 6 (the step of introducing the 16-position carbonyl in one step).

[0019]

[0020] Most importantly, step 4 (compound 6 → 1), where trace amounts of oxides or salts of transition metals cobalt, manganese or copper, such as MnO 2 , a good response effect can be obtained. It is speculated that, on the one hand, the transition metal cobalt, manganes...

Embodiment 1

[0027] Preparation of compound 4:

[0028] Under nitrogen protection, add 100g of compound 1 (4-AD), 110g of triethyl orthoformate, and 30g of absolute ethanol into the reaction flask, stir, cool down to 0-10°C, add 3g of p-toluenesulfonic acid, and monitor the completion of the reaction. Add 50 g of water and stir for 0.5 hours, add 8% sodium carbonate solution to adjust the pH to 8-9, stir for 2 hours, filter, and dry the filter cake to obtain 101 g of compound 4 with a yield of 92.1%.

[0029] Preparation of compound 6:

[0030] Under the protection of nitrogen, add 130g of ethyltriphenylphosphine bromide and 1000g of anhydrous tetrahydrofuran to the reaction bottle, add 60g of ethyltriphenylphosphine bromide under stirring, raise the temperature to 50-60°C for 2 hours, and add 22g of compound dropwise 4 (dissolved in 50g tetrahydrofuran), after the dropwise addition, control the temperature at 55-60°C and react for 20 hours until the reaction is complete. Cool down and a...

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Abstract

The invention relates to a method for preparing guggulsterone, wherein guggulsterone is prepared from a compound as shown in a formula 6 through a one-step method. The method specifically comprises the following steps: dissolving the compound as shown in the formula 6 in an organic solvent, adding a free radical initiator benzoyl peroxide and a catalyst, introducing air, and carrying out an oxidation reaction to obtain the guggulsterone, wherein the organic solvent contains ketone of C3-C6, and the catalyst comprises N-hydroxyphthalimide and oxides or salts of transition metal cobalt, manganese or copper. According to the invention, the target compound, namely guggulsterone, is obtained by directly introducing 16-site carbon group through air oxidation in a more effective manner, so that the steps are shorter, the yield is higher, and the method is more environment-friendly.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis / drug synthesis, and specifically relates to a method for preparing gugusterone. Background technique [0002] Gugusterone is also known as bisabolone, oxykusterone, chanosterone, sterosterone, or gestodene. Gugusterone has two isomers shown in Chemical Formulas 1 and 2 below. Chemical formula 1 is E-4,17(20)-pregnane-3,16-dione, also known as E-gugusterone. Chemical formula 2 is Z-4,17(20)-pregnane-3,16-dione, also known as Z-gugusterone. [0003] [0004] Numerous studies have shown that the biological activity of gugusterones is at least in part due to their role as farnesoid X receptor (FXR) ligands. Both isomers 1 and 2 were found to selectively regulate the expression of FXR gene, especially positively regulate the expression of cytochrome Cyp7A1, thereby inducing the catabolism of cholesterol in bile acids and reducing cholesterol levels. In the past, ancient steste...

Claims

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Application Information

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IPC IPC(8): C07J13/00B01J31/22B01J31/32
CPCC07J13/007B01J31/2217B01J31/32B01J2231/70Y02P20/584
Inventor 蒋红平龙能吟唐小海谢来宾
Owner HUNAN KEREY BIOTECH