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Oxidized iso-aporphine alkaloid derivative, synthetic method and application

A technology of alkaloid derivatives and oxidized isoaporphine, applied in the field of medicine, can solve the problems that have not been seen before, and achieve the effects of good medicinal value and significant in vitro anti-tumor activity

Inactive Publication Date: 2013-06-05
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no related 4,6-bis-(2-pyridyl)-5,6-dihydro-4H-1,5-diaza-benzo[de]cyclopentane [b ]-8-anthrone and related reports on its synthesis method and application

Method used

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  • Oxidized iso-aporphine alkaloid derivative, synthetic method and application
  • Oxidized iso-aporphine alkaloid derivative, synthetic method and application
  • Oxidized iso-aporphine alkaloid derivative, synthetic method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0043] Embodiment 1: Synthesis of 1-nitrogen-5-bromoxabenzanthrone

[0044] 1) Synthesis of intermediate 1 (4-bromophenethylamine):

[0045] Dissolve 0.2mol of lithium aluminum hydride in 200mL of anhydrous ether, and dissolve 0.2mol of 4-bromophenylacetonitrile in 50mL of anhydrous ether. Slowly add the anhydrous ether solution of 4-bromophenylacetonitrile dropwise. After the addition is complete, stir and react at room temperature for 6 hours, neutralize with saturated sodium sulfate solution until no bubbles are generated, filter the reaction solution with suction, wash the filter residue with chloroform, and depressurize The solvent was distilled off to obtain intermediate 1 (colorless and slightly viscous 4-bromophenethylamine liquid), with a yield of 40%;

[0046] 2) Synthesis of Intermediate 2:

[0047] Mix and dissolve 0.1 mol of phthalic anhydride and 0.1 mol of intermediate 1 in 200 mL of ethanol, reflux at 90°C for 8 hours, cool the reaction solution to room tempe...

Embodiment 2

[0059] Get 0.01mol of 1-nitrogen-5-bromoxabenzanthrone (prepared according to the method described in Example 1) and dissolve it in 25mL of n-pentanol, add 0.025mol of 2-(aminomethyl)pyridine, at 180°C Reflux reaction under the conditions until complete (TLC tracking detection, about 72h), cooling, a large amount of reddish-brown solids precipitated during the reaction, suction filtration, the filter residue was washed with ethanol and ether successively, and dried to obtain the crude product of the target product; the crude product of the target product was obtained with Chloroform (according to the amount of 60 milliliters of chloroform per gram of the target product crude product to calculate the amount of chloroform) after dissolving, go to silica gel column chromatography, elute with a mixed solvent composed of chloroform and methanol with a volume ratio of 50:1, and the eluent is evaporated to dryness solvent to obtain a reddish-brown solid product with a yield of about 9...

Embodiment 3

[0071] Take 0.01mol of 1-nitrogen-5-bromoxabenzanthrone and dissolve it in 50mL of n-pentanol, add 0.04mol of 2-(aminomethyl)pyridine, and reflux the reaction at 170°C until complete (TLC tracking detection , about 48h), cooling, the reaction process has a large amount of reddish-brown solid to separate out, suction filtration, filter residue is washed with ether, ethanol successively, dry, obtains target product crude product; The amount of chloroform is used to calculate the amount of chloroform) after dissolving, go to silica gel column chromatography, elute with a mixed solvent composed of chloroform and methanol with a volume ratio of 60:1, and the eluent is evaporated to dryness to obtain reddish-brown oxidized isoaporphine The yield of alkaloid derivative PPCA is about 80%.

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Abstract

The invention discloses a new oxidized iso-aporphine alkaloid derivative-4,6-dis-(2-pyridyl)-5,6-dihydro-4H-1,5-diaza-benzo[de]cyclopentane[b]-8-anthranone(PPCA for short), a synthetic method and an application. The PPCA synthetic method comprises the following steps: weighting 1-nitrogen-5-bromobenzanthrone and 2-(aminomethyl)pyridine, taking 1-nitrogen-5-bromobenzanthrone for dissolving in n-amyl alcohol, adding the weighted 2-(aminomethyl)pyridine and performing backflow reaction at the temperature of 140-180 DEG C, cooling, performing pumping filtration, washing the filter residue, and drying to obtain the oxidized iso-aporphine alkaloid derivative. The invention investigates the oxidized iso-aporphine alkaloid derivative has inhibition activity on the propagation of various human tumor cell strains such as HepG2, MGC80-3, SK-OV-3 and T-24, the result shows that the oxidized iso-aporphine alkaloid derivative has obvious external antineoplastic activity and has good latent medicinal value. A structural formula of PPCA is shown in a following formula.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an oxidized isoaporphine alkaloid derivative and a synthesis method and application thereof. Background technique [0002] Natural alkaloids are a series of natural product compounds with good potential medicinal value, which widely exist in various families and genera of traditional Chinese medicine plants; so far, more than a dozen oxidized isoaporphine-type natural alkaloids have been discovered And separated out, such as bat kryptonine, bat kryptonine, bat kryphanine, bat kefinoline and so on. [0003] Because the content of oxidized isoaporphine in natural plants is relatively low, for the consideration of improving efficiency and resource protection, domestic and foreign researchers are developing organic synthesis methods of oxidized isoaporphine. As early as 1953, King et al. first synthesized the mother nucleus of the oxidized isoaporphine alkaloid, that is, 1-azabenza...

Claims

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Application Information

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IPC IPC(8): C07D471/06A61K31/4748A61P35/00
Inventor 陈振锋梁宏刘延成覃其品
Owner GUANGXI NORMAL UNIV
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