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A novel thiazole compound xqh-3-6 against Streptococcus mutans and its application

A technology of streptococcus mutans and compounds, applied in the field of thiazole compounds and new thiazole compounds, to achieve small molecular weight, good killing effect and strong inhibitory effect

Inactive Publication Date: 2019-01-18
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, fluoride is widely used in the clinical treatment of dental caries, but leads to the selective growth of fluoride-resistant strains

Method used

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  • A novel thiazole compound xqh-3-6 against Streptococcus mutans and its application
  • A novel thiazole compound xqh-3-6 against Streptococcus mutans and its application
  • A novel thiazole compound xqh-3-6 against Streptococcus mutans and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of compound XQH-3-6

[0024] The synthetic route of compound XQH-3-6 is shown in the following reaction formula:

[0025]

[0026] Wherein: (a) 1-hydroxybenzotriazole (HOBT), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI), triethylamine, room temperature; ( b) ethyl acetate saturated hydrogen chloride solution, room temperature; or trifluoroacetic acid / dichloromethane; (d) triphosgene, anhydrous ethyl acetate, 0°C to reflux; (e) triethylamine, anhydrous tetrahydrofuran, 0°C to room temperature.

[0027] If the solvent involved in the reaction process needs to be dried, it is dried according to a commonly used standard drying method. Specific reaction process:

[0028] (1) Preparation of intermediate 4-tert-butyl-((5-nitrothiazol-2-yl)carbamoyl-1-carboxylic acid (1).

[0029] Dissolve 1-Boc-4-piperidinecarboxylic acid (1eq) in N, N dimethylformamide, then add HOBt (1.2eq) and EDCI (1.2eq) respectively, add triethyl...

Embodiment 2

[0035] Embodiment 2: the preparation of Streptococcus mutans

[0036] (1) The medium for cultivating Streptococcus mutans is Brain Heart Infusion medium (brand OXOID, product number CM1135). The main components of the medium are Brain infusion solids 12.5g / L, Beef heartinfusion solids 5.0g / L , Proteose peptone 10.0g / L, Glucose 2.0g / L, Sodiumchloride 5.0g / L, Di-sodium phosphate2.5g / L, pH 7.4±0.2. If solid medium is required, add 1.5% agar powder. Sterilize with damp heat at 115°C for 30 minutes, and cool down for use.

[0037] (2) The culture medium for Streptococcus mutans biofilm is brain heart infusion-sucrose medium. The preparation method is that the sucrose is made into 20% stock solution and sterilized by filtering with a 0.22 μm sterile filter, and the final concentration of 1% sucrose is added to the brain-heart infusion medium.

[0038] (3) Streptococcus mutans type strain UA159 and clinical strain UA246 were inoculated on the solid medium of brain heart infusion a...

Embodiment 3

[0042] Example 3: Activity detection of compound XQH-2-92 on streptococcus mutans planktonic cells

[0043] (1) Prepare Streptococcus mutans liquid and compound XQH-3-6 according to the method described in embodiment 2, will cultivate logarithmic phase (OD 600 =0.8~1.0) Streptococcus mutans UA159 and UA246 bacterium liquid were diluted with brain heart infusion liquid medium to a final concentration of 5×10 5 cfu / ml for use.

[0044] (2) The detection of the minimum inhibitory concentration of compound XQH-3-6 on planktonic cells of Streptococcus mutans UA159 and UA246 was carried out by micro broth dilution method. The final concentration of Streptococcus mutans in each well of a sterile 96-well plate was 5×10 5 cfu / ml, add the stock solution of compound XQH-3-6 prepared according to the above method to the first well and adjust to a final concentration of 256 mg / L, mix well, then pipette 150 μl to the second well, mix well and then pipette 150 μl To the 3rd well, serially...

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Abstract

The invention discloses a novel thiazole compound capable of inhibiting streptococcus mutans. The compound number is XQH-3-6, the molecular formula is C16H16ClN5O4S, the molecular weight is 409.85, and the Chinese name is N1-(3-chlorphenyl-N4-(5-nitrothiazole-2-yl))piperidine-1,4-dicarboxamide. Experiments show that the compound presents the good antibacterial activity and fungicidal activity on type strains and clinical strains of the streptococcus mutans in a floating state. Meanwhile, when the final concentration of the compound XQH-3-6 in a culture medium reaches 4 mg / L, the inhibition ratio of streptococcus mutans biological membrane reaches 97% or above. The compound is small in molecular weight and simple in structure, inhibition experiments prove that the compound has the advantages of being high in inhibition, good in killing effect and the like, growth of main pathogen-streptococcus mutans buoyant cells of caries and formation of a biological membrane can be significantly inhibited, the potential of preventing the caries is achieved, and the compound can serve as a novel targeted candidate drug for preventing the caries.

Description

technical field [0001] The invention relates to a thiazole compound, in particular to a novel thiazole compound XQH-3-6 resistant to Streptococcus mutans and its application. The compound can inhibit the growth of periodontal bacteria in the oral cavity, can be used to prevent and treat dental caries, and belongs to the technical field of preparation of medicines for prevention and treatment of oral diseases. Background technique [0002] Dental caries, commonly known as tooth decay, is a common chronic disease in the oral cavity. Caries develops slowly and causes irreversible damage to dental hard tissues. It is widely distributed and has a high incidence rate. It not only brings pain to individuals, but also causes a huge waste of medical resources. It has become a global problem that threatens human oral health. , the World Health Organization (WHO) listed it as one of the three major non-communicable diseases (cardiovascular disease, cancer and dental caries) that human...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12A61K31/454A61P1/02A61P31/02A01N47/38A01P1/00A61K8/49A61Q11/00A61Q17/00
CPCA01N47/38A61K8/4926A61Q11/00A61Q17/005C07D417/12
Inventor 李荀胡玮吴一波王川东丁坤王艳李星陆地刘孝涛
Owner SHANDONG UNIV
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