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Anti-ameba protozoon disease compounds of 8-Epigroshiemin and synthesis thereof

A technology of amoeba and synthetic method, applied in organic chemistry, anti-infective drugs, drug combination, etc., can solve the problems of low content, no further report on activity, and difficult synthesis

Inactive Publication Date: 2009-05-13
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(BarbettiP, Casinovi C G, Santurbano B, et al. A grosheimin epimer from Crepis virens. Coll Czec Chem. Commun, 1979, 44: 3123-3127) Since the content of this compound in plants is small and its synthesis is difficult, so about this Compound activity not further reported
At present, there is no report on the synthesis of this compound

Method used

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  • Anti-ameba protozoon disease compounds of 8-Epigroshiemin and synthesis thereof
  • Anti-ameba protozoon disease compounds of 8-Epigroshiemin and synthesis thereof
  • Anti-ameba protozoon disease compounds of 8-Epigroshiemin and synthesis thereof

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Embodiment

[0025] The synthetic method of the anti-amoeba compound Epigrosheimin [(—)-8-Epigrosheimin provided by the invention comprises the steps:

[0026]

[0027] The specific synthesis steps are described in detail as follows:

[0028] 1. The synthesis of the raw material 2-methyl-3-methoxymethyl-5-isopropenyl-cyclopentanecarbaldehyde (5-Isopropenyl-3-methoxymethoxy-2-methyl-cyclopentanecarbaldehyde) used in the reaction is the method with reference to the literature Synthesized with a yield of 50%. (Lee E, Yoon C H. Stereoselective favorskii rearrangement of carvone chlorohydrin: Expedient synthesis of (+)-dihydrone petalactone and (+)-iridomyrmecin. JChem Soc, Chem Commun, 1994: 479-481).

[0029] 2. Synthesis of Intermediate 1:

[0030]2-Methyl-3-methoxymethyl-5-isopropenyl-cyclopentanecarbaldehyde (300mg, 1.4mmol) and trimethylsilyl enol of γ-butyrolactone at -78°C A solution of boron trifluoride (0.27 mL, 2.1 mmol) in dichloromethane (2.0 mL) was added dropwise to a solut...

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Abstract

The invention relates to a synthetic method for an 8-Epigroshiemin compound against amoeba protozoiasis. The synthetic method comprises the following steps: catalyzing 5-Isopropenyl-3-methoxymethoxy-2-methyl-cyclopentanecarbaldehyde obtained by synthesis of carvone and trimethyl enol silicon ether of 1, 4-butyrolactone by Lewis acid to obtain an intermediate to further obtain intermediate diol; oxidizing the intermediate diol to form a lactonic ring, and hydrolyzing and acidifying the lactonic ring under alkaline condition; activating carbonyl by using Vilsmeier reagent, reducing and oxidizing the lactonic ring to obtain aldehyde, and catalyzing the aldehyde by the Lewis acid to obtain a ring-closed product three-dimensionally and specifically; and then introducing methane into the lactonic ring to obtain the target compound through protection removal and selective oxidization. The method synthesizes the compound with higher yield; and activity tests show that the compound has stronger resistance to amoeba protozoiasis activity, and can be used as a specific medicine for treating the amoeba protozoiasis.

Description

technical field [0001] The present invention relates to the chemical synthesis of natural sesquiterpene lactone active substances in plants, in particular to the synthesis method of an anti-amoeba compound 8-Epigroshiemin, specifically enantioselective synthesis Synthetic method of natural sesquiterpene lactone-epigrosheimin [(—)-8-Epigrosheimin with anti-amoeba activity. Starting from readily available raw materials in the market, optically pure natural products are obtained. The compound can be used as a bactericidal and anti-amoeba drug or its precursor. Background technique [0002] Amoeba can parasitize in human or animal tissue. The protozoan mostly parasitizes the intestines and livers of humans and animals, and rarely parasitizes the lungs, brain, and spleen, and invades the body in the form of trophozoites, thereby causing amoebic dysentery (expressed as acute and chronic amoebic dysentery) ) or parenteral infection (ie amebic liver abscess). Amebic enteropathy ...

Claims

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Application Information

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IPC IPC(8): C07D307/93C07D307/58A61P33/02
Inventor 徐效华杨海申乔晓晓谢龙观
Owner NANKAI UNIV
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