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Piplartine analogue, and preparation method and application thereof

A technology of piperamide and analogs, which is applied to the application field of substituted piperamide compounds and their preparation, and the preparation of antitumor drugs, can solve the problem of enhancing the antitumor activity and selectivity of compounds, and the ineffectiveness of piperamide activities. higher question

Inactive Publication Date: 2014-02-26
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These reported Piperamide analogs are relatively inactive, so it is necessary to carry out further structural modifications to enhance the antitumor activity and selectivity of the compound, reduce toxicity, and develop antitumor drugs with new mechanisms of action.

Method used

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  • Piplartine analogue, and preparation method and application thereof
  • Piplartine analogue, and preparation method and application thereof
  • Piplartine analogue, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076]Example 1: Synthesis of 3-chloro-5,6-dihydro-2(1H)-pyridone

[0077]

[0078] Dissolve 25.0 g of 2-piperidone in 250 ml of chloroform, cool to 0°C, add 158.0 g of phosphorus pentachloride, stir for 15 minutes, then heat to reflux for 3 hours. After cooling, the reaction solution was slowly poured into 500 ml of ice water, the aqueous layer was extracted three times with 50 ml of dichloromethane, the combined organic phases were washed with saturated brine, dried, and the solvent was evaporated to obtain a yellow oily liquid.

[0079] Dissolve 4.0 g of the product from the previous step in 12 ml of DMF, add 3.6 g of anhydrous lithium carbonate, and react at 120 degrees for 7 hours. After cooling, it was poured into ice water, extracted three times with 50 ml of dichloromethane, washed with saturated brine, dried, concentrated, and the residue was purified by column chromatography to obtain 1.1 g of the product with a yield of 35.1%.

[0080] 1 H-NMR (CDCl 3 ):7.11-7...

Embodiment 2

[0081] Example 2: Preparation of 3-morpholino-5,6-dihydro-2(1H)-pyridone

[0082]

[0083] Dissolve 1.3 g of 3-chloro-5,6-dihydro-2(1H)-pyridone and 0.9 g of morpholine in 5 ml of DMF, add 1.5 g of anhydrous lithium carbonate, raise the temperature to 130°C, and react for 3 hours. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography to obtain 0.6 g of white solid, with a yield of 30.2%.

[0084] 1 H-NMR (CDCl 3 ):6.15(s,1H),5.56(t,1H),3.82-3.85(m,4H),3.30-3.36(m,2H),2.87-2.90(m,4H),2.33-2.40(m,2H ).

Embodiment 3

[0085] Embodiment 3: Preparation of (E)-2-methyl-3-(3,4,5-trimethoxyphenyl)acrylic acid

[0086]

[0087] 2.0 grams of 3,4,5-trimethoxybenzaldehyde, 5.9 grams of 2-methylmalonic acid, 0.2 grams of piperidine and 20 milliliters of anhydrous pyridine were added to the flask, and refluxed for 24 hours. The solvent was evaporated under reduced pressure, the residue was dissolved in 50 ml of water, extracted three times with 20 ml of ethyl acetate, washed with water, dried, and the residue was purified by column chromatography to obtain 1.7 g of a white solid with a yield of 66.1%.

[0088] 1 H-NMR (CDCl 3 ):7.77(s,1H),6.69(s,2H),3.10(s,9H),2.19(s,3H).

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PUM

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Abstract

The invention relates to the technical field of medicines. Piplartine is alkaloid extracted from perennial herbaceous vine piper longum of piperaceae. The invention provides a Piplartine analogue, which comprises a cis-trans-isomer, and any arbitrary mixture in those forms or medicinal salt thereof, and the structural formula of the Piplartine analogue is shown in a general formula (I). The invention also provides a preparation method of substituted Piplartine compounds, and an application thereof in preparation of an antitumor medicament.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a class of substituted piperamide compounds, a preparation method thereof, and an application in the preparation of antitumor drugs. Background technique [0002] Piplartine is an alkaloid extracted from Piplartine, a perennial herbaceous vine of the Piperaceae family, Piplartine. Its chemical structure is as follows: [0003] [0004] Pharmacological tests have shown that Piperamide has multiple biological activities, such as being used for the treatment of nervous system diseases, the treatment of cardiovascular and cerebrovascular diseases, and antifungal, antidepressant and antitumor effects. WO2008147483 and WO2009038684 respectively describe the effects of Piperamide and its analogues in the treatment of progressive multiple demyelinating diseases of the central nervous system such as progressive multifocal leukoencephalopathy and neurological tissue-related diseases ca...

Claims

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Application Information

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IPC IPC(8): C07D211/86C07D401/06A61K31/4412A61K31/5377A61K31/4439A61P35/00A61P35/02A61P31/10A61P7/02A61P25/24A61P25/22A61P25/04A61P25/00A61P9/00
CPCC07D211/86C07D401/06
Inventor 缪震元张万年吴岳林盛春泉姚建忠庄春林
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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