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Application of 2-[(4-tert-butylthiazol-2-yl]imino]thiazoline-4-one in pharmacy

A technology of tert-butylthiazole and imino, which is applied in the application field of thiazole compounds, can solve the serious problems of dental caries prevention, and can inhibit the formation of planktonic cells and biofilms of Streptococcus mutans, with broad application prospects and inhibitory strong effect

Inactive Publication Date: 2018-10-23
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the large and long-term use of fluoride, Streptococcus mutans has begun to develop fluoride resistance (Hoelscher and Hudson, 1996), which makes the situation of caries prevention more severe

Method used

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  • Application of 2-[(4-tert-butylthiazol-2-yl]imino]thiazoline-4-one in pharmacy
  • Application of 2-[(4-tert-butylthiazol-2-yl]imino]thiazoline-4-one in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1: Preparation of 2-[(4-tert-butylthiazol-2-yl)imino]thiazolin-4-one

[0016] 4.36g (25mmol) 4-tert-butylthiazol-2-amine, 30ml dichloromethane, stir to dissolve, add 3.45g (25mmol) anhydrous potassium carbonate, stir at room temperature for 30min, drop 2ml (25mmol) chloroacetyl chloride, Reaction 1.5h. The reaction solution was poured into ice water, extracted with dichloromethane, washed with saturated sodium carbonate aqueous solution, combined organic phases, dried over anhydrous sodium sulfate, precipitated, and recrystallized from ethanol to obtain 5.50 g of white solid 1, yield 87.7%, m.p.113-115 ℃.

[0017] 2.30g (9mmol) of compound 1, 1.31g (13.5mmol) of potassium thiocyanate, dissolved in 30ml of ethanol, heated to reflux for 2.5h; cooled, precipitated solid, suction filtered, dried to obtain 2.10g of yellow solid 2 which is 2-[( 4-tert-butylthiazol-2-yl)imino]thiazolin-4-one, yield 90.0%, m.p.200~202°C.

[0018] 1 H NMR (CDCl 3 , 400MHz) δ: 1.33(s...

Embodiment 2

[0021] Embodiment 2: the cultivation of Streptococcus mutans

[0022] (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 it needs to be configured into a solid, 15g / L of agar powder needs to be added. Sterilize at 115°C for 30 minutes and cool down for use.

[0023] (2) The medium for cultivating Streptococcus mutans biofilm is brain heart infusion-sucrose medium, that is, sucrose with a final concentration of 1% is added to the brain heart infusion medium. Sucrose needs to be made into 20% stock solution in advance and sterilized by filtering with a 0.22 μm sterile filter.

[0024] (3) Streptococcus mutans type strain UA159 and Streptococcus mutans strain UA246 isolated from the oral cavity of den...

Embodiment 3

[0027] Embodiment 3: 2-[(4-tert-butylthiazol-2-yl) imino] thiazolin-4-one compound detects the activity of streptococcus mutans planktonic cells

[0028] (1) Prepare 2-[(4-tert-butylthiazol-2-yl)imino]thiazolin-4-one according to the method described in Example 1, accurately weigh the compound with an analytical balance, and add DMSO to Dissolve it, and then filter and sterilize it with a sterile filter with a pore size of 0.22 μm to make a stock solution with a final concentration of 1024 mg / L, and store it at -20°C until use;

[0029] Prepare Streptococcus mutans UA159 and UA246 bacterium liquid according to the method described in embodiment 2, it is cultivated to logarithmic phase and makes Streptococcus mutans bacterium liquid OD 600nm=0.8~1.0, diluted with brain heart infusion medium to a final concentration of 5×10 5 cfu / ml for use.

[0030] (2) The minimum inhibitory concentration of 2-[(4-tert-butylthiazol-2-yl)imino]thiazolin-4-one compound on the planktonic cells ...

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Abstract

The invention discloses an application of 2-[(4-tert-butylthiazol-2-yl]imino]thiazoline-4-one in preparation of drugs for inhibiting and killing streptococcus mutans type strains or in preparation ofdrugs for inhibiting formation of a streptococcus mutans type strain biofilm. Experiments prove that the compound shows good bacteriostatic and bactericidal activities against the streptococcus mutanstype strains in a floating state, and the inhibition rate of the compound to the streptococcus mutans biofilm reaches 99% or more when the final concentration of the compound in a culture medium reaches 4 mg / L. The compound can be used as a novel lead compound for preventing dental caries, and has broad application prospects in preparation of oral streptococcus mutans biofilm inhibitors.

Description

technical field [0001] The present invention relates to the application of a kind of thiazole compound, relate in particular to a kind of 2-[(4-tert-butylthiazol-2-yl) imino] thiazolin-4-one in the preparation inhibition and killing streptococcus mutans (Streptococcus mutans ) applications in drugs. Background technique [0002] Dental caries, commonly known as caries and tooth decay, is characterized by the demineralization of enamel and dentin and the decomposition of organic matter. It is a worldwide chronic disease induced by bacteria and is especially common in adolescents and children. Due to its high incidence and wide prevalence, dental caries has become one of the major oral diseases that seriously endanger human health (Pitts, 2004). Under normal circumstances, the microorganisms in the oral cavity are in a relatively stable physiological balance on the tooth surface, once this balance is broken, dental caries will be induced (Selwitz et al., 2007). Streptococcus...

Claims

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Application Information

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IPC IPC(8): A61K31/427A61P31/04A61P1/02
CPCA61K31/427A61P1/02A61P31/04
Inventor 张尚立宋超马剑峰
Owner SHANDONG UNIV
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