Quinoline thiocarbamide-pyridine organic compound and preparation method and application thereof

A kind of technology of quinoline thiosemicarbazide and organic compound, which is applied in the field of quinoline thiosemicarbazide-pyridine organic compound and preparation thereof, and can solve the problems of no synthesis method and application of quinoline thiosemicarbazide-pyridine organic compound and the like , to optimize biological properties, improve multi-targeting, and enhance inhibitory effects

Active Publication Date: 2018-09-11
HENAN UNIV OF URBAN CONSTR
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In current research, there is no relevant report on the synthesis method and application of quinoline thiosemicarbazone-pyridine organic compound

Method used

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  • Quinoline thiocarbamide-pyridine organic compound and preparation method and application thereof
  • Quinoline thiocarbamide-pyridine organic compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation steps of quinoline thiosemicarbazone-pyridine organic compound are as follows:

[0024] (1) Weigh 2-aminopyridine (7.6 g, 0.08 mol) into a single-necked flask, add carbon disulfide (9.6 mL, 0.16 mol), triethylamine (24 mL, 0.16 mol), heat and stir the mixture in a water bath until clear , stirred at room temperature for 24 h. Treatment: Take the mixture in the flask and filter, and after obtaining the filter residue, use a small amount of methanol to completely dissolve it to reach a hot saturated solution. Then, slowly add a small amount of saturated methanol solution containing a large amount of product into a large amount of ether solution, and the yellow product quickly reappears in the ether solution. Intermediate product A crystallized out. Yield: 53%.

[0025] (2) Weigh the obtained yellow product A (12 g) into a round bottom flask, add methanol (25 mL) and methyl iodide (3 mL), and stir at room temperature for 1 h to obtain a reddish-brown reac...

Embodiment 2

[0031] The preparation steps of quinoline thiosemicarbazone-pyridine organic compound are as follows:

[0032] (1) Weigh 2-aminopyridine (7.6 g, 0.08 mol) into a single-necked flask, add carbon disulfide (4.8 mL, 0.08 mol), triethylamine (12 mL, 0.08 mol), heat and stir the mixture in a water bath until clear , stirred at room temperature for 12 h. Treatment: Take the mixture in the flask and filter, and after obtaining the filter residue, use a small amount of methanol to completely dissolve it to reach a hot saturated solution. Then, slowly add a small amount of saturated methanol solution containing a large amount of product into a large amount of ether solution, and the yellow product quickly reappears in the ether solution. Intermediate product A crystallized out. Yield: 44%.

[0033](2) Weigh the obtained yellow product A (10 g) into a round bottom flask, add methanol (20 mL), methyl iodide (2.5 mL), and stir at room temperature for 1 h to obtain a reddish-brown reacti...

Embodiment 3

[0037] The preparation steps of quinoline thiosemicarbazone-pyridine organic compound are as follows:

[0038] (1) Weigh 2-aminopyridine (7.6 g, 0.08 mol) into a single-necked flask, add carbon disulfide (7.2 mL, 0.12 mol), triethylamine (18 mL, 0.12 mol), heat and stir the mixture in a water bath until clear , stirred at room temperature for 18 h. Treatment: Take the mixture in the flask and filter, and add the filter residue to ether solution, stir and wash at room temperature for 10-20 min, filter, and dry the filter residue in air to obtain intermediate product A. Yield: 85%.

[0039] (2) Weigh the obtained yellow product A (10 g) into a round bottom flask, add methanol (35 mL) and methyl iodide (3 mL), and stir at room temperature for 1.5 h to obtain a reddish-brown reaction solution. Treatment: Slowly pour the reaction solution into about 600 mL of warm water, and white flocs precipitate out. After standing for 1.5 days, pale yellow needle-like crystals precipitate out...

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Abstract

The invention discloses a quinoline thiocarbamide-pyridine organic compound and preparation method and application thereof, wherein the structural formula is shown in the description, the thiosemicarbazide is combined with the quinoline group, so that the novel compound has multiple advantages of thiophanate, quinoline and pyridine pharmacophore, and possesses different types of pharmacodynamic groups and diverse structural characteristics, is beneficial to reducing the toxic and side effects of single functional group in the field of biological activity, and the compounds is endowed with multiple biological targets, the water solubility of the organic compound is optimized and the uptake ability of the focus tissue is improved. The thiourea, the nitrogen heterocyclic group pyridine and the quinoline are combined into an organic compound molecule, thereby being favorable for constructing the metal organic complex with different structural characteristics from the metal center, and further optimizing the biological performance thereof.

Description

technical field [0001] The invention relates to the field of preparation of thiosemicarbazide-based compounds, in particular to a quinoline thiosemicarbazone-pyridine organic compound and its preparation method and application. Background technique [0002] The thiocarbonyl group of thiosemicarbazide has high chemical activity and low acute toxicity to mammals. Thiosemicarbazide derivatives have good pharmacological and biological activities, and have anti-malignant, antibacterial, and anti-leukemia properties, so they have attracted the attention of medical and chemical researchers. The nature of the substituents of the derivatives has a significant impact on their biological activity, and the thiourea group can improve the water solubility of the compounds. Thiosemicarbazides have the same coordination atoms as biological compounds such as amino acids, peptides, proteins, enzymes, and ribonucleic acids. Their coordination with metal ions through nitrogen atoms and sulfur ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A61P35/00
CPCA61P35/00C07D401/12
Inventor 胡继勇赵金安廖春丽张军帅陈树芳毛瑞娜晋锦锦
Owner HENAN UNIV OF URBAN CONSTR
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