Compounds containing phenothiazinyl and 1,3,4-thiadiazolyl mannich bases and their preparation methods and applications

A phenothiazine-based and thiadiazolyl-based technology, applied in the field of chemical synthesis, can solve the problems of short reaction time, long reaction time, and low yield, and achieve the effects of short reaction time, simple post-treatment, and high yield

Active Publication Date: 2016-04-06
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, according to the existing literature, most of the Mannich reactions have defects such as long reaction time, low yield, and the use of complex catalysts. In order to overcome the above disadvantages, my research group finally obtained a reaction The method of synthesizing Mannich base with shorter time, higher yield and without any catalyst, finally carried out the antibacterial experiment research on this series of novel compounds, the results show that these compounds have the physiological function of inhibiting the growth of Gram active

Method used

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  • Compounds containing phenothiazinyl and 1,3,4-thiadiazolyl mannich bases and their preparation methods and applications
  • Compounds containing phenothiazinyl and 1,3,4-thiadiazolyl mannich bases and their preparation methods and applications
  • Compounds containing phenothiazinyl and 1,3,4-thiadiazolyl mannich bases and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1) Add 0.001 mol of phenothiazine, 0.002 mol of formaldehyde solution with a mass concentration of 37% to 40% (manufacturer: Tianjin Best Chemical Co., Ltd.) and 0.001 mol of 2-amino-1 into a dry three-necked flask, 3,4-thiadiazole, then add 10 mL of ethanol with a mass concentration of 95%, and stir and react at room temperature for 5 hours. At this time, when TLC monitors that the raw material point of phenothiazine disappears, the reaction solution is obtained; The developer is a mixture of ethyl acetate and petroleum ether, and the volume ratio of ethyl acetate and petroleum ether is 1:5;

[0038] 2) Evaporate the solvent in the reaction solution, and the residue in the three-necked flask is the crude product, which is recrystallized with absolute ethanol to obtain 2-(N-methylphenothiazine)amino-1 in the form of white powder, 3,4-Thiadiazole, 76% yield.

[0039] IR (KBr pellet method, ν / cm -1 ): 3487, 3088, 1648, 1601, 1447, 1327, 763.

[0040] 1 HNMR (CDCl 3 ,...

Embodiment 2

[0042]1) Add 0.001 mol of phenothiazine, 0.003 mol of formaldehyde solution with a mass concentration of 37% to 40% (manufacturer: Tianjin Best Chemical Co., Ltd.) and 0.001 mol of 2-amino-5- Methyl-1,3,4-thiadiazole, then add 10 mL of ethanol with a mass concentration of 95%, and stir and react at room temperature for 6 hours. At this time, when TLC monitors that the raw material point of phenothiazine disappears, the reaction solution is obtained ; Wherein, the developer of TLC is mixed by ethyl acetate and sherwood oil, and the volume ratio of ethyl acetate and sherwood oil is 1:5;

[0043] 2) Evaporate the solvent in the reaction solution, and the residue in the three-necked flask is the crude product, which is recrystallized with absolute ethanol to obtain 2-methyl-5-(N-methylphenothiazine in the form of white powder ) amino-1,3,4-thiadiazole with a yield of 90%.

[0044] IR (KBr pellet method, ν / cm -1 ): 3487, 3085, 2972, 2871, 1650, 1602, 1449, 1333, 768.

[0045] 1...

Embodiment 3

[0047] 1) Add 0.001 mol of phenothiazine, 0.003 mol of formaldehyde solution with a mass concentration of 37% to 40% (manufacturer: Tianjin Best Chemical Co., Ltd.) and 0.002 mol of 2-amino-5- Ethyl-1,3,4-thiadiazole, and then add 11 mL of ethanol with a mass fraction of 95%, and stir and react at room temperature for 6 hours. At this time, when TLC monitors that the raw material point of phenothiazine disappears, the reaction solution ; Wherein, the developer of TLC is mixed by ethyl acetate and sherwood oil, and the volume ratio of ethyl acetate and sherwood oil is 1:5;

[0048] 2) Evaporate the solvent in the reaction solution, and the residue in the three-necked flask is the crude product, which is recrystallized with absolute ethanol to obtain 2-ethyl-5-(N-methylphenothiazine ) amino-1,3,4-thiadiazole with a yield of 80%.

[0049] IR (KBr pellet method, ν / cm -1 ): 3489, 3090, 2970, 2928, 2873, 2855, 1650, 1603, 1449, 1330, 766.

[0050] 1 HNMR (CDCl 3 , 400M, TMS int...

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Abstract

The invention discloses a Mannich alkali compounds containing phenothiazine group and 1,3,4-thiadiazole group as well as a preparation method and an application thereof. The preparation method comprises the following steps of: stirring and reacting a phenothiazine, formaldehyde solution and 1,3,4-thiadiazole derivatives used as raw materials in the presence of ethyl alcohol used as a solvent at a room temperature; then steaming out the solvent in the obtained reaction solution, and recrystallizing the remainder, namely, a crude product, in a reactor, so as to obtain Mannich alkalis containing phenothiazine group and 1,3,4-thiadiazole group. The preparation method disclosed by the invention is simple in operation steps, convenient in aftertreatment, and high in yield; moreover, the compounds can be applied to preparation for anti-gram bacteria medicines.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to Mannich base compounds containing phenothiazine groups and 1,3,4-thiadiazolyl groups, their preparation methods and applications. Background technique [0002] Phenothiazine compounds are heterocyclic compounds containing N and S atoms, which can be used in a wide range of applications, such as biomedicine, polymerization inhibitors, antioxidants in lubricants, conductive polymer materials, and dyes. Among them, since phenothiazine and its derivatives have high pharmacological activity and biological activity, the drug application of phenothiazine compounds has become a research hotspot for scientific researchers. [0003] 1,3,4-Thiadiazoles are an important class of heterocyclic compounds, which are widely used in industry, agriculture and medicine. In terms of medicine, it has antibacterial, anticonvulsant, anti-depression, anti-stress, lower blood pressure and ant...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12A61K31/5415A61P31/04
CPCY02A50/30
Inventor 尹大伟王捷刘玉婷刘蓓蓓张晓莉吕博
Owner SHAANXI UNIV OF SCI & TECH
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