3,4,5-trihydroxy gallic acrylamide benzene sulfonamide derivatives as well as preparation method and application thereof

A technology of galloamide and benzenesulfonamide, which is applied in the preparation of sulfonamides, drug combinations, and pharmaceutical formulations, and can solve the problems of low transmembrane permeability and weak pharmacological activity of drugs

Active Publication Date: 2014-12-10
GUANGXI UNIV
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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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  • 3,4,5-trihydroxy gallic acrylamide benzene sulfonamide derivatives as well as preparation method and application thereof
  • 3,4,5-trihydroxy gallic acrylamide benzene sulfonamide derivatives as well as preparation method and application thereof
  • 3,4,5-trihydroxy gallic acrylamide benzene sulfonamide derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 3,4,5-Trihydroxygallosulfamethoxazole

[0027] 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 removing part of THF by pressure evaporation, let it stand for 48 hours, filter the insoluble matter, wash with 1M / L hydrochloric acid, then wash with distilled water, filter, dry in vacuum, and recrystallize in methanol-THF system to obtain 3,4,5-tri...

Embodiment 2-5

[0029] With the operation of embodiment 1, replace the sulfamethoxazole in the embodiment 1 with sulfathiazole sodium, sulfachloropyridazine sodium, sulfachlorpyrazine sodium, sulfamidine respectively, obtain 3,4,5-trihydroxy gallosulfonamide Sodium thiazole, 3,4,5-trihydroxygalloylsulfachloropyridazine, 3,4,5-trihydroxygalloylsulfachlorpyrazine and 3,4,5-trihydroxygallosulfonamide.

Embodiment 6-10

[0031] Take an appropriate amount of 3,4,5-trihydroxygalloylsulfamethoxazole, 3,4,5-trihydroxygalloylsulfathiazole, sulfachloropyridazine sodium, sulfachloropyrazine sodium and 3,4,5-tris Hydroxygallosulfamidine is respectively dissolved in 0.1M / L aqueous solution of sodium hydroxide or potassium hydroxide to prepare a certain concentration of sodium or potassium salt of the above-mentioned p-galloamide benzenesulfonamide compound.

[0032]

[0033] In the above-mentioned Examples 1-5, in order to confirm the structure of gallic acid derivatives, the inventors analyzed the hydrogen spectra, carbon spectra, and mass spectra of the derivatives, and confirmed that the characterization data of the structural compounds are shown in Table 1 below:

[0034] Table 1 Structure and spectral data of 3,4,5-trihydroxygallanamide benzenesulfonamide compound

[0035]

[0036] Two, the antibacterial effect embodiment of 3,4,5-trihydroxy gallamide benzene sulfonamide compound

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Abstract

The invention relates to 3,4,5-trihydroxy gallic acrylamide benzene sulfonamide compounds as well as a preparation method and an application of the compounds in preparation of medicines for resisting bacteria and promoting the growth of cartilage cells. Most of compounds in the compounds 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 compounds can be applied to preparation of medicines for treating osteoarthritis.

Description

technical field [0001] The present invention relates to medicine, preparation method and application, in particular to gallic acid compounds, preparation method and application. Background technique [0002] Gallic acid, also known as gallic acid or gallic acid (chemical formula C7H6O5, molecular weight 170.12), is a polyphenolic compound that exists in nature and is widely found in plants such as gall, grapes, sumac, and tea. A large number of documents have confirmed that gallic acid and its extracts have the biological activities of promoting apoptosis, anti-inflammation, anti-mutation, and anti-oxidation. In addition, there are also reports in the literature that it can promote the formation of chondrocytes in the treatment of joint diseases. important role. 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. Sul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/22C07D237/20C07D277/52C07D261/16C07C303/40C07C311/64A61K31/635A61K31/63A61P31/04A61P19/08A61P19/02
CPCC07C311/64C07D237/20C07D241/22C07D261/16C07D277/52Y02A50/30
Inventor 林翠梧林霄刘布鸣郑立罗轩黄艳陈海兰彭小玉
Owner GUANGXI UNIV
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