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5h‑[1,2,4]triazolo[5,1‑b][1,3]thiazide derivatives and their application
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A technology of triazoles and derivatives, applied in the field of medicine, can solve problems such as drug resistance or pharmacokinetic defects
Inactive Publication Date: 2017-04-12
SHIJIAZHUANG UNIVERSITY
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[0004]Existing acetylcholinesterase inhibitors such as tacrine, stigmine, galantamine, etc., still have drug resistance or pharmacokinetic defects
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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. Slowly add 20.6 g (0.13 mol) of 4-fluorobenzoyl chloride dropwise at 0-5°C, and the dropwise addition is completed in 20 minutes, and react at 15°C for 2 hours to end the reaction. 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) + .
[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 present invention discloses 5H-[1,2,4]triazolo[5,1-b][1,3]thiazine derivatives of general formula I or pharmaceutically acceptable hydrates and salts thereof, including Its stereoisomers or tautomers, wherein R1 and R2 in formula I are independently hydrogen, methyl, halogen, hydroxyl, methoxy, acetyl, propionyl, nitro or alkoxy. The 5H-[1,2,4]triazolo[5,1-b][1,3]thiazine derivatives of the present invention have obvious inhibitory effect on acetylcholinesterase, and are used to strengthen the Memory in Alzheimer's patients. The invention also relates to a preparation method of the compound and its application in the preparation of a medicine 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...
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