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Curcuminoid condensed aromatic amine Schiff base derivative, as well as preparation method and application thereof in preparation of antibacterial medicaments

A technology of aromatic amine Schiff base and curcuminoids, which is applied in the field of synthesizing curcuminoid condensed 3, 5-diarylamine Schiff base derivatives, can solve the problems of low bioavailability and poor water solubility of curcumin, and achieve Good antibacterial effect, long antibacterial effective time, improved bioavailability and antibacterial activity

Inactive Publication Date: 2013-06-19
TANGSHAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This new chemical can be made by reacting certain substances together at specific sites within them or combining different types of atoms that make up these materials into complex structures called catechins. These specialized forms are used for making medicines like vancomycin because they have strong bacteriostats against staphlybacillis (Streptomyces), streptococcidium spp., pseudomonas aeruginosa, etc.. They also enhance their ability to fight off other harmful microorganisms such as Escherichia coli O157 cells without causing any damage from being exposed during treatment.

Problems solved by technology

This patented describes different ways to modify cisplatin structures to increase its ability to dissolve certain molecules like calcium ion into solution when administered topically without causing side reactions. These modifications include modifying specific parts of the platinarium skeleton called tertyrins, adding other types of chelating agents onto these sites, changing the type of metal atom involved in each step, replacing atoms within the framework of the original structure, forming new ones based on changes made during manufacturing processes, etc., resulting in improved properties including better blood stability and reduced unwanted side effects associated therewith.

Method used

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  • Curcuminoid condensed aromatic amine Schiff base derivative, as well as preparation method and application thereof in preparation of antibacterial medicaments
  • Curcuminoid condensed aromatic amine Schiff base derivative, as well as preparation method and application thereof in preparation of antibacterial medicaments

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Example 1: Curcuminoid derivatives 1,7-bis(4-dimethylaminophenyl)-3,5-bis(4-fluorophenylimino)-1,6-heptadiene (DAEF) synthesis.

[0017] Add 2 mmol of 4-fluoroaniline in a three-necked flask, dissolve in 5 mL of absolute ethanol, then add catalytic amount of formic acid and anhydrous aluminum chloride, and slowly add 1 mmol of the above product curcumin analog DAEO and 12 mL of anhydrous aluminum chloride dropwise under stirring. Mixed solution of water and ethanol, heated to reflux reaction, nitrogen protection, reacted for 15 hours, and thin-layer chromatography detected the reaction. After the reaction, the organic phase was extracted, concentrated, and separated by silica gel thin-layer chromatography (petroleum ether: ethyl acetate = 2:1), a yellow solid product was obtained with a yield of 12.4%. And through FTIR, MALDI-TOP, 1 HNMR and other methods confirmed the structure of the compound. IR(KBr) ν: 3046, 2982, 2841, 1645, 1633, 1500-1600, 1355, 1233cm -1 Ma...

Embodiment 2

[0018] Embodiment 2: curcuminoid derivative 1,7-bis(4-dimethylaminophenyl)-3,5-bis(4-chlorophenylimino)-1,6-heptadiene (DAECl) synthesis.

[0019] Add 2mmol of 4-chloroaniline in a three-necked flask, dissolve in 5mL of absolute ethanol, then add catalytic amount of formic acid and anhydrous aluminum trichloride, and slowly add 1mmol of the above-mentioned product curcumin analog DAEO and 15mL of anhydrous aluminum chloride dropwise under stirring. Mixed solution of water and ethanol, heated to reflux reaction, nitrogen protection, reacted for 8 hours, and thin-layer chromatography detected the reaction. After the reaction, the organic phase was extracted, concentrated, and separated by silica gel thin-layer chromatography (petroleum ether: ethyl acetate = 3:1), a yellow solid product was obtained with a yield of 22.7%. And through FTIR, MALDI-TOP, 1 HNMR and other methods confirmed the structure of the compound. IR(KBr) ν: 3036, 2979, 2839, 1642, 1631, 1490-1580, 1350, 733...

Embodiment 3

[0020] Example 3: Curcuminoid derivative 1,7-bis(4-dimethylaminophenyl)-3,5-bis(4-bromophenylimino)-1,6-heptadiene (DAEBr) synthesis.

[0021] Add 2 mmol of 4-bromoaniline in a three-necked flask, dissolve in 5 mL of absolute ethanol, then add catalytic amount of formic acid and anhydrous aluminum chloride, and slowly add 1 mmol of the above product curcumin analog DAEO and 15 mL of anhydrous aluminum chloride dropwise under stirring. The mixed solution of water and ethanol was heated to reflux for reaction, protected by nitrogen, and reacted for 3 hours. Thin-layer chromatography detected the reaction. After the reaction, the organic phase was extracted and separated by silica gel thin-layer chromatography (petroleum ether: ethyl acetate=4: 1), to obtain a tan solid product with a yield of 34.7%. And through FTIR, MALDI-TOP, 1 HNMR and other methods confirmed the structure of the compound. IR(KBr) ν: 3032, 2966, 2834, 1640, 1627, 1488-1575, 1346, 623cm -1 Mass Spectrum M...

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Abstract

The invention relates to a curcuminoid condensed aromatic amine Schiff base derivative and application thereof in preparation of antibacterial medicaments, belonging to the technical field of synthesized curcuminoid condensed 3, 5-diaromatic amine Schiff base derivatives and applications thereof. According to the technical scheme, the structure formula is shown in the description, wherein R is halogen on benzene ring para-position: fluorine, chlorine, bromine, and iodine. The curcuminoid condensed aromatic amine Schiff base derivative is used for preparing the antibacterial medicaments and used for resisting staphylococcus aureus and streptococcus. The curcuminoid condensed aromatic amine Schiff base derivative disclosed by the invention has an obvious inhibiting effect on the Staphylococcus aureus and the streptococcus; and compared with curcumin wich is a parent body, the curcuminoid condensed aromatic amine Schiff base derivative has the advantages that the antibacterial effect is better, the antibacterial effective time is longer, and the bioavailability and the antibacterial activity are improved.

Description

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Claims

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Application Information

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Owner TANGSHAN NORMAL UNIV
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