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N-gallic amide-pyrimidine phenyl sulfonamide derivative as well as preparation method and application thereof

A technology of pyrimidinylbenzenesulfonamide and sulfadiazine is applied in the field of medicine and preparation, and can solve the problems of weak pharmacological activity, low drug transmembrane permeability and the like

Active Publication Date: 2014-12-10
湖南沛草堂中医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the strong hydrophilicity of gallic acid, the transmembrane permeability of the drug is low, so the pharmacological activity shown in the human body is weaker than that of its ester derivatives

Method used

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  • N-gallic amide-pyrimidine phenyl sulfonamide derivative as well as preparation method and application thereof
  • N-gallic amide-pyrimidine phenyl sulfonamide derivative as well as preparation method and application thereof
  • N-gallic amide-pyrimidine phenyl sulfonamide derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 3,4,5-Triacetylgalloylsulfadiazine

[0035] In an oil bath at 80°C, mix gallic acid with 3 times (m:V) acetic anhydride and stir for 12 hours, add 15 times the volume of distilled water and let it stand for 48 hours, filter the insoluble matter, and dry it in vacuum to obtain 3,4,5- Triacetyl gallic acid; reflux 3,4,5-triacetyl gallic acid and thionyl chloride in an oil bath at 70°C for 6 hours, and recover thionyl chloride under reduced pressure to obtain 3,4,5-triacetyl base galloyl chloride; mix 3,4,5-triacetyl galloyl chloride and sulfadiazine sodium in tetrahydrofuran, add a small amount of pyridine as a catalyst, stir in ice bath for 2 hours and room temperature for 12 hours, then add distilled water, reduce After part of the THF was evaporated under pressure, it was allowed to stand for 48 hours, and the insoluble matter was collected by filtration, dried in vacuo, and recrystallized in a methanol-THF system to obtain 3,4,5-triacetylgalloylsulfadiazine.

Embodiment 2-4

[0037] With the operation of Example 1, replace the sodium sulfadiazine in Example 1 with sulfa-methoxine, sulfa-p-methoxine, and sulfamethoxine respectively, and the rest of the operations are the same as in Example 1 to obtain 3,4,5-triacetyl Galloyl sulfa-methoxine, 3,4,5-triacetyl sulfa-methoxine, 3,4,5-triacetyl sulfa-methoxine.

Embodiment 5

[0039] 3,4,5-Trihydroxygallosulfamethazine

[0040] The same operation as in Example 1, using sulfamethazine instead of sulfamethazine in Example 1, after obtaining 3,4,5-triacetyl sulfamethazine, dissolve it in tetrahydrofuran, add hydrochloric acid at 60°C for hydrolysis After 6 hours, add distilled water, evaporate part of tetrahydrofuran under reduced pressure at 80°C, let it stand, filter the insoluble matter, dry it in vacuum, and recrystallize in methanol-tetrahydrofuran system to obtain 3,4,5-trihydroxygallosulfamethazine .

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Abstract

The invention relates to an N-gallic amide-pyrimidine phenyl sulfonamide compound as well as a preparation method and an application of the compound in preparation of medicines for resisting bacteria and promoting the growth of cartilage cells. The N-gallic amide-pyrimidine phenyl sulfonamide compound and a water soluble salt thereof have certain bacteriostatic action on staphylococcus aureus, escherichia coli, pseudomonas aeruginosa, acinetobacter, proteusbacillus vulgaris, pulmonary tuberculosis and the like in vitro, and have an obvious promotion effect on proliferation of bone cells, and synthesis of total protein and glycosaminoglycan in chondrocyte, the gene levels of proteoglycan, II collagen and SOX9 gene can also be regulated upwards, the gene level of I collagen can be inhibited, secretion and synthesis of extracellular matrix of the cartilage can be promoted, and the compound can be applied to preparation of the medicines for treating osteoarthritis.

Description

Technical field [0001] The present invention involves medicine and preparation methods and uses, and specifically involves a type of N-non-sulfinamine-pyrazide basin sulfonamide compounds and preparation methods and uses. Background technique [0002] Gallic acid (gallic acid) is also known as pentaic acid or chorine acid (chemical C7H6O5, molecular weight 170.12). It is a polyphenol -type compound existing in nature.A large number of literatures have confirmed that the extracts that do not eat child acid and contain non -meal acid have biological activity that promotes apoptosis, anti -inflammatory, anti -mutation, and antioxidant.Important role.However, due to the strong hydrophilicity of the child's acid, the transparency of the drug is low, so the pharmacological activity in the human body is weaker than the derivatives of its ester.Sulfa drugs are a general term with drugs with aminozene sulfide structures. They have good endometrium permeability, distributed in human tissue...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/42C07D239/47C07D239/52C07D241/22C07D237/20A61K31/635A61P31/04A61P19/02A61P19/08
CPCC07D237/20C07D239/42C07D239/47C07D239/52C07D241/22Y02A50/30
Inventor 林霄刘布鸣林翠梧郑立柴玲黄艳刘琴邱宏聪陈明生
Owner 湖南沛草堂中医药科技有限公司
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