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Preparation method and application of fluorine-containing aromatic ring carboxylic acid tetramer compound

A technology of aromatic ring carboxylic acid and tetramer, which is applied in the application field of anti-neuroblastoma, can solve the problems of rare neuroblastoma, undisclosed inhibition of neuroblastoma, etc., achieve inhibition of cell activity, preparation method Simple, fat-soluble effect

Inactive Publication Date: 2020-04-07
WEIFANG MEDICAL UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In current studies, it has been reported that organotin carboxylates have inhibitory effects on a variety of tumors, but there are few reports on the effective inhibition of neuroblastoma
Hengyang Normal University reported a series of organotin carboxylate compounds. Pharmacological experiments showed that the organotin compounds have the activity of inhibiting various tumor cells including breast cancer cells, lung cancer cells and colon cancer cells. Neuroblastoma Activity

Method used

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  • Preparation method and application of fluorine-containing aromatic ring carboxylic acid tetramer compound
  • Preparation method and application of fluorine-containing aromatic ring carboxylic acid tetramer compound
  • Preparation method and application of fluorine-containing aromatic ring carboxylic acid tetramer compound

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Effect test

Embodiment 1

[0021] Preparation of fluorine-containing aromatic ring carboxylic acid tetramer compound: Add 1.0 mmol of 2-amino-4,5-difluoro-benzoic acid, 1.0 mmol of sodium ethoxide, 1.0 mmol of dibutyldichloride to a standard Schlenk tube Chloride tin, 20mL of methanol, stirred at 50°C for 5 hours, and evaporated on a rotary basis to obtain a light yellow powdery solid; recrystallized with dichloromethane-n-hexane to obtain a light yellow transparent crystal, which is the fluorine-containing aromatic ring carboxylic acid tetramer body compound; wherein, the volume ratio of dichloromethane to n-hexane is 6:1. Yield 85%, melting point 112-114°C.

[0022] Through infrared spectrum analysis and elemental analysis and X-ray single crystal diffraction, the results are as follows:

[0023] Infrared spectrum (KBr, cm -1 ): v as (C=O) 1641, 1598; v s (C-O) 1387, 1290; v as (Sn-C)606, v s (Sn-C) 502, v(Sn-O-Sn) 686, 649, v(Sn-O) 479.

[0024] Elemental Analysis: Calculated Value C 60 h 88...

Embodiment 2

[0028] Preparation of fluorine-containing aromatic ring carboxylic acid tetramer compound: add 1.0 mmol of 2-amino-4,5-difluoro-benzoic acid, 1.0 mmol of sodium ethoxide, and 1.0 mmol of dibutyltin dichloride to the flask, 40mL of methanol was stirred at 50°C for 6 hours, and then evaporated to obtain a light yellow solid; recrystallized with dichloromethane-n-hexane to obtain a light yellow transparent crystal, which was a fluorine-containing aromatic ring carboxylic acid tetramer compound; , the volume ratio of dichloromethane to n-hexane is 3:1. Yield 78%, melting point 112-114°C.

Embodiment 3

[0030] Preparation of fluorine-containing aromatic ring carboxylic acid tetramer compound: add 1.0 mmol of 2-amino-4,5-difluoro-benzoic acid, 1.0 mmol of sodium ethoxide, and 1.0 mmol of dibutyltin dichloride to the flask, 60mL of methanol was stirred at 50°C for 5 hours, and then evaporated to obtain a light yellow solid; recrystallized with dichloromethane-n-hexane to obtain a light yellow transparent crystal, which was a fluorine-containing aromatic ring carboxylic acid tetramer compound; , the volume ratio of dichloromethane to n-hexane is 4:1. Yield 82%, melting point 112-114°C.

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Abstract

The invention discloses a fluorine-containing aromatic ring carboxylic acid tetramer compound, and a preparation method and an application thereof. The preparation method comprises the following steps: adding 1.0 mmol of 2-amino-4,5-difluorobenzoic acid, 1.0 mmol of sodium ethoxide, 1.0 mmol of dibutyltin dichloride and 20-60 mL of methanol into a reaction container, performing stirring at 50 DEGC for 5 hours, and carrying out rotary evaporation to obtain a faint yellow powdery solid; and recrystallizing the faint yellow powdery solid with dichloromethane-n-hexane to obtain a faint yellow transparent crystal that is the fluorine-containing aromatic ring carboxylic acid tetramer compound, wherein a volume ratio of dichloromethane to n-hexane is 3:1 to 6:1. The fluorine-containing aromaticring carboxylic acid tetramer compound has anti-neuroblastoma activity. In the formula, n-Bu represents an n-butyl group.

Description

technical field [0001] The invention relates to a novel fluorine-containing aromatic ring carboxylic acid tetramer compound, its preparation method, and the application of the compound in the preparation of anticancer drugs, especially the application of antineuroblastoma. Background technique [0002] Neuroblastoma (Neuroblastoma, NB) is a neuroendocrine tumor that can originate from any neural crest of the sympathetic nervous system, and its main metastasis routes are lymphatic and hematogenous. About 35% of patients with localized lesions have regional lymph node infiltration, and hematogenous metastasis mainly occurs in bone marrow, bone, liver and skin, and there may be brain and lung metastasis in the terminal stage or recurrence. The disease mostly occurs in children under the age of 10, accounting for about 8-10% of childhood tumors, and the annual incidence rate is about 1 / 100,000, which is only lower than leukemia and central nervous system tumors. Neuroblastoma ha...

Claims

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Application Information

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IPC IPC(8): C07F7/22A61P35/00
CPCA61P35/00C07F7/2224
Inventor 宋伟国李法辉甲宗青吴晓刚
Owner WEIFANG MEDICAL UNIV
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