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An anti-caries and anti-bacterial thiazole compound and its preparation method

A technology of compounds and compound structural formulas, applied in the field of medicine, can solve problems such as difficulty in maintaining long-acting and effective antibacterial effects, and achieve the effect of reducing growth vitality

Inactive Publication Date: 2020-07-03
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If there is only antibacterial effect and no inhibitory effect on biofilm, it is difficult to maintain long-term and effective antibacterial effect, and therefore it is very easy to produce bacterial resistance

Method used

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  • An anti-caries and anti-bacterial thiazole compound and its preparation method
  • An anti-caries and anti-bacterial thiazole compound and its preparation method
  • An anti-caries and anti-bacterial thiazole compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The preparation of embodiment 1 formula (I) compound

[0057] The synthetic route is:

[0058]

[0059] Reagents and reaction conditions used in the synthetic route: (a) EDCI, DMAP, anhydrous N,N-dimethylformamide, room temperature; (b) HCl / ethyl acetate saturated solution, room temperature, 15min; (c) carbonic acid Potassium, dioxane / water (V:V=1:1), room temperature, 30min.

[0060] Concrete preparation process comprises the following steps:

[0061] (1) Preparation of (3-((5-nitrothiazol-2-yl)carbamoyl)phenyl)carbamate tert-butyl ester (intermediate 1)

[0062] Dissolve 2-amino-5-nitrothiazole (1mmol) and 3-(Boc-amino)benzoic acid (1.2mmol) in 12mL of anhydrous N,N-dimethylformamide, then add EDCI (2mmol) and DMAP (2mmol), reacted at room temperature for 12h, added 30mL of ethyl acetate to the reaction solution for dilution, washed twice with 1mol / L HCl aqueous solution (2×30mL), washed twice with saturated sodium bicarbonate solution (1 × 30 mL), and then w...

Embodiment 2

[0067] Embodiment 2. Antibacterial activity experiment of formula (I) compound

[0068] 1. Preparation of Streptococcus mutans UA159 strain (S.mutans UA159) and formula (I) compound

[0069] The Streptococcus mutans UA159 strain used in the present invention is a type strain, and the reference genome number in the NCBI database (http: / / www.ncbi.nlm.nih.gov / ) is NC_004350. The Streptococcus mutans UA246 strain used in the present invention is a clinical strain isolated from the oral cavity of a caries patient. The most suitable culture medium is preferably BrainHeart Infusion medium (Brain infusion solids 12.5g / L, Beef heart infusion solids 5.0g / L, Proteose peptone 10.0g / L, Glucose 2.0g / L, Sodium chloride 5.0 g / L, Di-sodium phosphate 2.5g / L, pH 7.4±0.2), static culture at 37°C, the most suitable condition for anaerobic culture.

[0070] (1) The medium for cultivating Streptococcus mutans is Brain Heart Infusion medium (brand OXOID, product number CM1135). The main component...

Embodiment 3

[0085] Embodiment 3. The effect experiment of formula (I) compound on oral cavity normal bacteria

[0086] The experimental procedure was the same as in Example 2, and the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of the compound on normal oral bacteria L.delbrueckii CICC 6032, V.denticariosi KQ-ETV-9, and V.rogosae WZH3n were tested. The results are shown in Table 2.

[0087] Table 2. Antibacterial and bactericidal activity results (unit μg / mL) of the compound of formula (I) to normal oral bacteria

[0088]

[0089] It can be seen from Table 2 that the compound of formula (I) has no effect on normal oral bacteria, which is even smaller than the positive control drug chlorhexidine.

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Abstract

The invention provides an anti-caries antibacterial thiazole compound and a preparation method thereof. The thiazole compound is of a structure of formula (I) as shown in the specification. The compound is small in molecular weight and simple in structure, antibacterial tests show that the compound has the characteristics of being food in inhibition, good in killing effect, and the like, the compound is capable of remarkably inhibition formation of streptococcus mutan biological membranes, degrading growth activity of mature streptococcus mutan biological membranes and in addition inhibiting acid generation of streptococcus mutan and has the potential of being developed as a medicine for effectively preventing and treating caries.

Description

technical field [0001] The invention relates to the field of medicine, in particular to an anti-caries and anti-bacterial thiazole compound and a preparation method thereof. Background technique [0002] Dental caries is a common chronic infectious disease that occurs in dental hard tissues. Through a series of processes such as bacterial biofilm accumulation, metabolic acid production, and local demineralization of dental tissue, tooth tissue defects eventually occur. Streptococcus mutans (abbreviated as Streptococcus mutans) is the main cariogenic bacteria recognized today. On the basis of physical adsorption, it produces adhesion to the tooth surface through surface virulence factors (such as acid production and acid resistance, in vitro adhesion, and synthesis of extracellular polysaccharides). Attachment, and finally continue to aggregate to form a cariogenic biofilm. Since the interior of the biofilm tissue provides a relatively stable living environment for the growt...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/46A61K31/426A61P1/02A61P31/04
CPCA61P1/02A61P31/04C07D277/46
Inventor 李荀尹志成
Owner SHANDONG UNIV
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