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Peganumine A alkaloid structure simplifier and application thereof

A technology of simplified substances and alkaloids, applied in the field of medicine, can solve the problems of further improvement of anti-tumor activity, limited source of alkaloids, difficulties in separation and extraction, etc., and achieve simple chemical synthesis routes, easy to realize synthetic methods, and easy to obtain synthetic raw materials Effect

Active Publication Date: 2021-06-25
AIR FORCE MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this alkaloid has scientific problems such as limited sources, difficult separation and extraction, poor water solubility, high difficulty in total synthesis, and further improvement of antitumor activity (Org Lett 2014, 16, 4028-4031; J Am Chem Soc 2016, 138, 11148-11151 ), which limits its development into a drug, and needs to optimize its structure to further improve its anti-tumor activity and druggability

Method used

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  • Peganumine A alkaloid structure simplifier and application thereof
  • Peganumine A alkaloid structure simplifier and application thereof
  • Peganumine A alkaloid structure simplifier and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of compound I-1

[0039]

[0040] The first step, the preparation of intermediate 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylic acid (compound 3)

[0041] According to the method reported in the literature (Organic Letters, 2014, 16, 4194-4197), in 50 ml of water, add tryptamine, compound 1 (1.0 g, 6.24 mM) and glyoxylic acid, compound 2 (0.47 g, 6.3 mM ), stirring and reacting at room temperature for 2 hours, a white precipitate was obtained, which was filtered by suction and dried in vacuo to obtain compound 3, 1.05 g of a white solid, with a yield of 77.8%.

[0042] The second step, the preparation of intermediate 6,7-dimethoxy-3,4-dihydroisoquinoline (compound 5)

[0043]

[0044] In 2 ml DMSO, add 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, compound 4 (0.1 g, 0.52 mM) and 2-iodobenzoic acid (IBX, 0.15 g, 0.52 mM), react in DMSO at room temperature for 1 hour. After the reaction was complete, add saturated NaCl to wash with water, extra...

Embodiment 2

[0049] It was prepared according to the method steps of Example 1, the raw material of the first step was changed to compound 6, and the second and third steps were prepared according to the method of Example 1.

[0050]

[0051] Compound I-2 was obtained as a white solid 28 mg, with a yield of 27%.

Embodiment 3

[0053] It was prepared according to the method steps of Example 1, the raw material of the first step was changed to compound 8, and the second and third steps were prepared according to the method of Example 1.

[0054]

[0055] Compound I-3 was obtained as a white solid 45 mg with a yield of 45%.

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Abstract

The invention discloses a Peganumine A alkaloid structure simplifier, a stereoisomer or a pharmaceutical salt thereof. The structure is shown in the following general formula: each substituent group is defined in the specification. The simplified structure of the Peganumine A alkaloid provided by the invention has a relatively obvious proliferation inhibition effect on liver cancer HepG2, lung cancer A549 and intestinal cancer HCT116, and the anti-tumor activity of part of compounds is higher than the anti-liver cancer HepG2 activity of Peganumine A reported in literatures.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a Peganumine A alkaloid structure simplification and a salt thereof, a preparation method and an application. Background technique [0002] Peganumine A is a β-carboline alkaloid. According to the literature Org Lett 2014,16,4028-4031, Peganumine A has broad-spectrum anti-tumor activity, such as the IC of leukemia cell HL-60, breast cancer cell MCF-7, prostate cancer cell PC-3 and liver cancer cell HepG2 50 5.8, 8.5, 40.2 and 55.4 μM, respectively. However, this alkaloid has scientific problems such as limited sources, difficult separation and extraction, poor water solubility, high difficulty in total synthesis, and further improvement of antitumor activity (Org Lett 2014, 16, 4028-4031; J Am Chem Soc 2016, 138, 11148-11151 ), which limits its development into a drug, and it is necessary to optimize its structure to further improve its anti-tumor activity and drug...

Claims

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Application Information

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IPC IPC(8): C07D471/22A61P35/00
CPCC07D471/22A61P35/00
Inventor 王胜正兰杼煊周翼鹏赵鹏帅张基泉崔敏萱贺优优卓振建
Owner AIR FORCE MEDICAL UNIV
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