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Preparation method of smallanthus sonchifolitus diterpene acid compound and compound obtained by using preparation method

A technology of agonist diterpene acids and compounds, applied in the field of chemical synthesis

Active Publication Date: 2014-06-25
珍奥集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no report about the synthetic method of these four compounds

Method used

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  • Preparation method of smallanthus sonchifolitus diterpene acid compound and compound obtained by using preparation method
  • Preparation method of smallanthus sonchifolitus diterpene acid compound and compound obtained by using preparation method
  • Preparation method of smallanthus sonchifolitus diterpene acid compound and compound obtained by using preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] Example 1: (2Z,6Z,10Z)-12-Hydroxy-6-(hydroxymethyl)-10-methyl-2-(4-methylpent-3-enyl)dodeca - Preparation of 2,6,10-trienecarboxylic acid (Compound A)

[0107] The synthetic route of compound A is as follows:

[0108]

[0109]

[0110] Synthesis of Compound IX-a

[0111]

[0112] Add methylmagnesium iodide (166mL, 500mmol) into 400mL of anhydrous ether, and cool to 0°C in an ice-salt bath. To this solution was slowly added dropwise a solution of cyclopropylmethyl ketone (42 g, 500 mmol) in anhydrous ether (100 mL). During the dropwise addition, the temperature should not be higher than 5°C. After the dropwise addition was completed, stirring was continued at room temperature for 2 hours. Slowly pour this reaction solution into a solution of dilute sulfuric acid (200mL concentrated sulfuric acid, 500mL water) cooled to 0°C in advance. Stir at room temperature for an additional 1 hour. The aqueous phase obtained by liquid separation was extracted with eth...

Embodiment 2

[0147] Example 2: (2Z,6Z,10Z)-12-Hydroxy-6-(hydroxymethyl)-10-methyl-2-(4-methyl-3-methylenepentenyl)dodeca-2 , Synthesis of 6,10-trienecarboxylic acid (Compound C)

[0148] The synthetic route of compound C is as follows:

[0149]

[0150] Synthesis of Compound IV-b

[0151]

[0152] 2,3-Dimethyl-1-butene (8.3g, 98.16mmol) and paraformaldehyde (2.46g, 81.8mmol) were successively added to 170mL of anhydrous dichloromethane, cooled to 0°C in an ice bath. To this solution was slowly added dropwise Me 2AlCl in n-hexane (100 mL, 90 mmol, 0.9 M). After the dropwise addition was completed, stirring was continued overnight at room temperature. Pour 5mL NaH into the reaction solution under ice bath 2 PO 4 solution, precipitated, and 10% hydrochloric acid was added dropwise until the precipitate was completely dissolved. The organic phase was separated, the aqueous phase was extracted with dichloromethane (2x200 mL), the combined organic phases were dried over anhydrous so...

Embodiment 3

[0161] Example 3: (R,2Z,6Z)-10-Hydroxy-6-(hydroxymethyl)-10-methyl-2-(4-methylpent-3-enyl)dodeca-2,6, Synthesis of 11-trienecarboxylic acid (compound B)

[0162] The synthetic route of compound B is as follows:

[0163]

[0164] Synthesis of Compound XII-b

[0165]

[0166] 4-Dimethylaminopyridine (50 g, 410 mmol) and acetic anhydride (80 mL) were sequentially added to a solution of (-)-linalool (46 g, 300 mmol) in 800 mL of acetonitrile. The reaction solution was heated to reflux, and continued to reflux overnight with stirring. After the reaction solution was cooled, 1.5 L of ethyl acetate was added for dilution, washed with 0.1N HCl solution (1 L) and saturated brine (1 L) successively, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and purified by column chromatography (200-300 mesh normal phase column chromatography silica gel, mobile phase petroleum ether: ethyl acetate = 10:1) to obtain XII-b, 44g, a colorless oil...

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PUM

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Abstract

The invention discloses a preparation method of a smallanthus sonchifolitus diterpene acid compound and a compound obtained by using the preparation method. The smallanthus sonchifolitus diterpene acid is prepared by reacting a compound as shown in the specification with an acidifying agent, and by performing a series of oxidation reaction, reduction reaction and hydrolysis reaction. The smallanthus sonchifolitus diterpene acid compound and a midbody compound thereof can be prepared by using the method disclosed by the invention, in-vitro experience shows that a compound A has good inhibition activity for alpha-glucosidase, the activity degree is equivalent to that of a diabetes therapeutic medicine glucobay, and the compound can be applied to preparation of anti-diabetic medicines.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to the chemical preparation of agonist diterpene acid compounds (and pharmaceutically acceptable salts thereof) and the compounds obtained by the method. Background technique [0002] Yagong (Smallanthus sonchifolitus (Proepp. & Endl.) H. Robinson, formerly known as Polymnia sonchifolia), Asteraceae (Asteraceae), tubular flower subfamily (Heliantheae) plants, native to the Andes at an altitude of 880-3500 meters, from Venezuela Eyes to northeastern Argentina. Yagong planting has spread all over other continents. It was originally planted in a small area in several states of the United States, and then sold in supermarkets as a special vegetable in New Zealand. In the 1980s, Yagong was introduced from New Zealand to Japan in Asia, and then introduced It has been introduced to Italy, Germany, France, Czech Republic, South Korea, Brazil, Russia and other countries, and has b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/42C07C51/09A61K31/191A61P3/10C07C69/73C07C69/16C07D303/16C07C33/02C07F9/40
CPCC07C29/147C07C33/02C07C51/09C07C59/42C07C67/08C07C67/29C07C67/343C07C69/145C07C69/16C07C69/73C07C69/738C07D303/16C07F9/4015
Inventor 陈玉琦董锋曾峥吴靓武广龙于宝辉
Owner 珍奥集团股份有限公司
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