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5H-[1, 2, 4] triazole [5, 1-b] [1, 3] thiazide derivative and application

A technology of triazole and thiazide, applied in the field of medicine, can solve problems such as drug resistance or pharmacokinetic defects

Inactive Publication Date: 2015-09-23
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]Existing acetylcholinesterase inhibitors such as tacrine, stigmine, galantamine, etc., still have drug resistance or pharmacokinetic defects

Method used

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  • 5H-[1, 2, 4] triazole [5, 1-b] [1, 3] thiazide derivative and application
  • 5H-[1, 2, 4] triazole [5, 1-b] [1, 3] thiazide derivative and application
  • 5H-[1, 2, 4] triazole [5, 1-b] [1, 3] thiazide derivative and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of 5-(4-fluorophenyl)-3-mercapto-1,2,4-triazole

[0021] Add 9.1 g (0.1 mol) of thiosemicarbazide and 100 mL of dichloromethane into a 250 mL three-necked flask, stir and dissolve in an ice-water bath, and then add 10.3 g (0.13 mol) of pyridine. 20.6g (0.13mol) of 4-fluorobenzoyl chloride was slowly added dropwise at 0-5°C, and the dropwise addition was completed within 20 minutes. After 2 hours of reaction at 15°C, the reaction was terminated. A large amount of white solid appeared in the system and was filtered. Dissolve the obtained white solid in 80 mL of 5% sodium hydroxide solution by mass fraction, heat to reflux for 2 hours, cool down to room temperature, adjust the pH to 5-6 with dilute hydrochloric acid with a mass fraction of 3.65%, a large amount of light yellow solid precipitates, filter , recrystallized to obtain 17.2 g of 5-(4-fluorophenyl)-3-mercapto-1,2,4-triazole, yield 88.2%, ESI-MS (m / z): 196.2(M +H) + .

Embodiment 2

[0023] Preparation of 5-(4-chlorophenyl)-3-mercapto-1,2,4-triazole

[0024] Thiosemicarbazide 9.1g (0.1 mol), dichloromethane 100 mL, pyridine 10.3g (0.13 mol) and 4-chlorobenzoyl chloride 22.75g (0.13mol) According to the method of Example 1, 5-(4-chloro Phenyl)-3-mercapto-1,2,4-triazole 18.3g, yield 86.7%, ESI-MS (m / z): 212.3(M+H) + .

Embodiment 3

[0026] 2-(4-fluorophenyl)-7-(4chlorophenyl)-5H-[1,2,4]triazolo[5,1-b][1,3]thiazine (L1) preparation

[0027] Add 1.95g (0.01mol) of 5-(4-fluorophenyl)-3-mercapto-1,2,4-triazole and 2.47g (0.01mol) of 4'-chloro-3-bromopropiophenone in 50 mL of acetic acid was dissolved and refluxed for 3 hours. After the reaction was monitored by TLC, it was cooled to room temperature. The reaction solution gradually precipitated solids. After suction filtration, washing with water, and ethanol recrystallization, 2.15 g of white crystals were obtained, with a yield of 62.73%. 1 H-NMR (300MHz, DMSO), δ (ppm): 3.61 (H, d), 6.40 (H, t), 7.30 (2H, d, J =8.4Hz), 7.34(2H, d, J =8.4Hz), 7.44(2H, d, J =8.4Hz), 7.77(2H, d, J =8.4Hz); ESI-MS (m / z): 344.1 (M+H) + .

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Abstract

The invention discloses a 5H-[1, 2, 4] triazole [5, 1-b] [1, 3] thiazide derivative with a general formula I, or a pharmaceutically acceptable aquo-complex and salts of the derivative; the derivative comprises a stereisomer or a tautomer, wherein R1 and R2 in the formula I are respectively independent hydrogen, methyl, halogen, hydroxyl, methoxyl, acetyl, propiono, nitro or alkoxy. The 5H-[1, 2, 4] triazole [5, 1-b] [1, 3] thiazide derivative has an obvious inhibiting effect on acetylcholin esterase, and is used for improving the memory of a patient suffering from dementia and Alzheimer's disease. The invention also relates to a preparation method of the compound and an application in preparation of a drug for treating Senile Dementia.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to 5H-[1,2,4]triazolo[5,1-b][1,3]thiazine derivatives and their preparation methods and as acetylcholinesterase inhibitors , an application for improving memory in patients with dementia and Alzheimer's disease. Background technique [0002] Alzheimer's disease is associated with the degeneration of cholinergic neurons in the basal forebrain. As a result of said degeneration, patients suffering from this disease exhibit marked attenuations in acetylcholine synthesis, choline acetyltransferase activity, acetylcholinesterase activity, and choline absorption. [0003] Acetylcholinesterase inhibitors are known to be effective in increasing cholinergic activity and thus may be used to improve memory in Alzheimer's disease patients. By inhibiting acetylcholinesterase, the compound increases levels of the neurotransmitter acetylcholine in the brain, thereby enhancing memory. [0004] T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04A61K31/542A61P25/28
CPCC07D513/04
Inventor 刘斯婕张宝华雷霓何敬宇史兰香郭瑞霞
Owner SHIJIAZHUANG UNIVERSITY
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