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Heteroaromatic ring compound with thiosemicarbazone structure unit and preparation method and application of compound

A technology of thiosemicarbazone and structural unit, which is applied in the directions of organic chemistry, drug combination, anti-tumor drugs, etc., can solve the problem of low inhibition effect on gastric cancer cell proliferation and so on.

Active Publication Date: 2019-06-28
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Thiosemicarbazones and their compounds refer to a class of compounds formed by condensation of multifunctional thiosemicarbazides with appropriate aldehydes or ketones. Due to their wide range of chemical and biological effects, medicinal chemists have attracted more and more attention. , which have a wide range of biological activities such as antibacterial, antiviral, antiparasitic and anticonvulsant; at the same time, due to their multifunctionality as ligands, they can produce a wide variety of coordination modes, and their C=N group Groups and N, S heteroatoms can form stable complexes with a variety of metal ions (such as Fe, Cu, Zn, etc.), and are a class of excellent metal ion chelating agents. Concern, but the inhibitory effect on the proliferation of gastric cancer cells is not high

Method used

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  • Heteroaromatic ring compound with thiosemicarbazone structure unit and preparation method and application of compound
  • Heteroaromatic ring compound with thiosemicarbazone structure unit and preparation method and application of compound
  • Heteroaromatic ring compound with thiosemicarbazone structure unit and preparation method and application of compound

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preparation example Construction

[0098] The present invention provides the preparation method of the aromatic heterocyclic compound containing the structural unit of thiosemicarbazone described in the above technical scheme, comprising the following steps:

[0099] (1) Mix the compound having the structure shown in formula II, hydrazine hydrate and solvent I, and carry out a nucleophilic addition reaction to obtain the compound having the structure shown in formula III;

[0100] (2) the compound having the structure shown in formula III, R 2 -R 3Mixing with solvent II, and carrying out condensation reaction under the action of a catalyst, to obtain the aromatic heterocyclic compound containing the structural unit of thiosemicarbazone having the structure shown in formula I;

[0101]

[0102] In the present invention, unless otherwise specified, all raw materials are commercially available products well known to those skilled in the art.

[0103] In the present invention, the compound having the structure...

Embodiment 1

[0120] (1) At a stirring speed of 650rpm, the compound (1mmol) having the structure shown in Formula II-1 and 80wt% hydrazine hydrate aqueous solution (4mmol) were successively added to methanol (AR, 5mL) at a rate of 7° C. / min The heating rate was raised to 70°C, refluxed and stirred for 5h (TLC monitored the reaction process), and after standing to cool to room temperature, the cup-shaped suction filter was used for suction filtration, and suction filtration was performed under 0.1MPa pressure for 20min to obtain 150mg of solid matter; The substance was dissolved in methanol (AR, 2 mL) in a water bath at 50°C, and then recrystallized on standing to obtain 130 mg of the compound having the structure shown in Formula III-1; the yield was 78.8%, and the purity was 95%.

[0121] The structure of formula Ⅱ-1 is The structure of formula III-1 is

[0122] The compound having the structure shown in formula III-1 is a white solid with a melting point of 144-145°C;

[0123] The a...

Embodiment 2

[0129] (1) According to the method of step (1) of Example 1, the compound with the structure shown in formula III-2 is prepared, the only difference is that the compound with the structure shown in formula II-1 is replaced with the compound with the structure shown in formula II-2 compound;

[0130] The structure of formula Ⅱ-2 is The structure of formula III-2 is

[0131] The compound having the structure shown in formula III-2 is a white solid with a melting point of 169-170°C, a yield of 72.3%, and a purity of 95%;

[0132] The analysis results are as follows: 1 H NMR (400MHz, DMSO-d6, ppm) δ9.23(s, 2H, NH, D 2 Oexchangeable), 7.65(d, J=6.6Hz, 2H, Ar-H), 7.46(d, J=8.7Hz, 2H, Ar-H), 4.86(s, 2H, -NH 2 ). 13 C NMR (100MHz, DMSO-d6, ppm) δ179.25, 138.76, 130.71, 125.54, 115.99. HR-MS (ESI), calcd.C 7 h 8 BrN 3 S, [M+Na] + m / z: 267.9520, found: 267.9523.

[0133] (2) According to the method of step (2) of Example 1, the compound having the structure shown in formula...

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Abstract

The invention relates to the technical field of medicine chemistry, in particular to a heteroaromatic ring compound with a thiosemicarbazone structure unit and a preparation method and application ofthe compound. The heteroaromatic ring compound with the thiosemicarbazone structure unit is chelated with metal ions in gastric cancer cells to form a stable complex, and accordingly the proliferationactivity of the gastric cancer cells MGC803 is inhibited. It is proved through a result of an embodiment that compared with a compound 3-AP, the heteroaromatic ring compound with the thiosemicarbazone structure unit has good proliferation inhibition activity on the gastric cancer cells MGC803.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to an aromatic heterocyclic compound containing a thiosemicarbazone structural unit and a preparation method and application thereof. Background technique [0002] Malignant tumors, especially gastric cancer, are a serious threat to human health. In addition to the development and improvement of early preventive diagnosis techniques for tumors, the development of new and efficient anti-tumor drugs is the most basic means of treating tumors. Studies have shown that transition metal ions such as FeII / III, CuI / II and ZnII play an extremely important role in the metabolic process of normal cells, and are the basic guarantee for cell growth and proliferation. Excessive metal ions will cause cytotoxicity, while insufficient may cause Leading to metabolic disorders or cell death, metal ions participate in various biochemical reactions in cells, especially play an important role...

Claims

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Application Information

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IPC IPC(8): C07D209/14C07D209/08C07D213/53C07D333/22C07D207/335C07D233/64C07D213/61C07D213/64A61P35/00
Inventor 刘宏民马立英张鑫荟马勤陶源源郑甲信
Owner ZHENGZHOU UNIV
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