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Rare earth complex with brominated oxybicuculline as a ligand, its synthesis method and application

A synthesis method and compound technology, applied in the field of rare earth complexes and their synthesis

Active Publication Date: 2021-04-06
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on rare earth complexes and their synthetic methods using bromo-oxidized bicuculline (abbreviated as Br-DCO) obtained by introducing a bromine atom on the A ring C3 of DCO as a ligand.

Method used

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  • Rare earth complex with brominated oxybicuculline as a ligand, its synthesis method and application
  • Rare earth complex with brominated oxybicuculline as a ligand, its synthesis method and application
  • Rare earth complex with brominated oxybicuculline as a ligand, its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1: the synthesis of brominated oxidized bicuculline i.e. Br-DCO

[0059] Synthesized according to the aforementioned synthetic route, specifically comprising the following steps:

[0060] 1) Synthesis of compound (2):

[0061] Dissolve 72g of 3,4-dimethoxyphenylacetic acid in 600mL of glacial acetic acid, stir at room temperature for 1h, then add 7.2g of bromine in glacial acetic acid (60mL), continue to react for 2h, then add 200mL of ice water, white A precipitate was formed, filtered, and the filter cake was recrystallized with methanol to obtain 96 g of compound (2), with a yield of about 95%.

[0062] Compound (2) is a white solid, ESI-MS m / z 273.02[(2)-H] - , 13 C-NMR (500MHz, DMSO) δ: 41.0816 (C-2), 56.2538 (C-5), 56.4330 (C-6), 114.9042 (C-9), 115.7982 (C-3), 115.9616 (C-8 ), 127.4302(C-10), 148.5825(C-4), 148.9687(C-8), 172.0429(C-1), 1 H-NMR (500MHz, DMSO) δ: 3.6021 (2H, S, H-2), 3.7120 (3H, S, H-5), 3.7346 (3H, S, H-6), 6.9880 (1H, S, H -3), ...

Embodiment 2

[0093] Embodiment 2: the synthesis of Br-DCO

[0094] Repeat Example 1, the difference is:

[0095] In steps 3)-5), the first organic solvent involved is changed to ethanol;

[0096] In step 4), reducing agent is changed into lithium borohydride;

[0097] In step 5), adjust the pH=8 of the system, and use chloroform as the extractant instead;

[0098] In step 6), adjust the pH of the system to 10, change the amount of palladium acetate to 3% of the mass of compound (6), change the second organic solvent to DMAC, and use dichloromethane as the extractant;

[0099] In step 7), adjust the pH=9 of the system;

[0100] In step 8), the first organic solvent involved is changed to ethyl acetate, and the extractant is changed to ethyl acetate;

[0101] In step 9), the amount of manganese acetate (Ⅲ) is changed to 5 times of the mass of compound (9), and the eluent when eluted on the silica gel column is composed of dichloromethane and methanol in a volume ratio of 25-30:1 mixed s...

Embodiment 3

[0103] Embodiment 3: the synthesis of Br-DCO

[0104] Repeat Example 1, the difference is:

[0105] In step 3), the first organic solvent involved is changed to n-butanol;

[0106] In step 4), the first organic solvent involved is changed to n-propanol, and the reducing agent is changed to potassium borohydride;

[0107] In step 5), the first organic solvent involved is changed to methanol to adjust the pH of the system to 10;

[0108] In step 6), adjust the pH of the system to 10, change the amount of palladium acetate to 2% of the mass of compound (6), change the second organic solvent to DMAC, and use ethyl acetate as the extractant;

[0109] In step 7), adjust the pH of the system to 8.5;

[0110] In step 8), the first organic solvent involved is changed to methanol, and the extractant is changed to dichloromethane;

[0111] In step 9), the amount of manganese acetate (Ⅲ) is changed to 4 times of the mass of compound (9), and the eluent when eluted on the silica gel co...

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Abstract

The invention discloses a kind of rare earth complex with bromo-oxidized bicuculline as a ligand, its synthesis method and application. The rare earth complex is obtained by dissolving bicuculline and a rare earth metal salt in a solvent system and performing a coordination reaction under heating conditions; wherein, the rare earth metal salt is LaCl 3 ·6H 2 O or CeCl 3 ·6H 2 O; the solvent system is a combination of chloroform and one selected from methanol or ethanol, wherein the volume ratio of chloroform to methanol or ethanol is 2:1-3.5:1. The results of in vitro tests show that the bromo-oxidized bicuculline-lanthanum rare earth complex T-24 tumor cell line has anti-proliferation activity and has potential medicinal value.

Description

technical field [0001] The invention relates to the field of metal coordination compounds, in particular to a rare earth complex with bromo-oxidized bicuculline as a ligand and a synthesis method and application thereof. Background technique [0002] Bicuculline is mainly derived from Dicentra spectabilis (Dicentra spectabilis), a plant of Papaveraceae, and Stephania dicentrinifera, aliased as Tong Ke Ning or Shangui Cine. Some researchers have isolated biologically active aporphine, isoquinoline and bisisoquinoline alkaloids from O.leucoxylon by means of separation. These compounds contain bicuculline, which has anti-tumor, analgesic and sedative properties. role and antibacterial biological activity. S-bicuculline can be isolated from Lindera megaphylla (Lauraceae), and anti-tumor research on it has found that it has significant anti-tumor activity against human hepatoma HuH-7. In the in vitro activity study of S-bicuculline on twenty-one human tumor cells from seven dif...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/00A61P35/00
CPCA61P35/00C07B2200/13C07F5/003
Inventor 梁宏顾运琼陈振锋刘延成黄克斌
Owner GUANGXI NORMAL UNIV
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