2-phenyl-6-benzoyl-thiazolo[3,2-b][1,2,4]-triazole derivative and application thereof
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A benzoyl, 2-b technology, applied in the field of medicine, can solve problems such as drug resistance or pharmacokinetic defects
Inactive Publication Date: 2015-09-09
SHIJIAZHUANG UNIVERSITY
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Problems solved by technology
[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 0.1 mol of thiosemicarbazide and 100 mL of dichloromethane into a 250 mL three-necked flask, stir in an ice-water bath to dissolve, and then add 0.13 mol of pyridine. Slowly add 0.13 mol of 4-fluorobenzoyl chloride dropwise at 0-5°C, complete the dropwise addition in 20 minutes, react at 15°C for 2 hours, and 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] 0.1 mol of thiosemicarbazide, 100 mL of dichloromethane, 0.13 mol of pyridine and 0.13 mol of 4-chlorobenzoyl chloride according to the method in Example 1 to obtain 5-(4-chlorophenyl)-3-mercapto-1,2, 4-Triazole 18.3g, yield 86.7%, ESI-MS (m / z): 212.3(M+H) + .
Embodiment 3
[0026] Preparation of 5-{4-[2-(1-piperidinyl)ethoxy]phenyl}-3-mercapto-1,2,4-triazole
[0027] 0.1 mol of thiosemicarbazide, 100 mL of dichloromethane, 0.13 mol of pyridine and 0.13 mol of 4-[2-(1-piperidinyl)ethoxy]benzoyl chloride according to the method in Example 1 to obtain 5-{4- [2-(1-piperidinyl)ethoxy]phenyl}-3-mercapto-1,2,4-triazole 24.3g, yield 79.9%, ESI-MS (m / z): 305.1( M+H) + .
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Abstract
The invention discloses a 2-phenyl-6-benzoyl-thiazolo[3,2-b][1,2,4]-triazole derivative disclosed as General Formula I or pharmaceutically acceptable hydrates and salts thereof, including stereomer or tautomers of the 2-phenyl-6-benzoyl-thiazolo[3,2-b][1,2,4]-triazole derivative. In the Formula I, R1 and R2 are respectively and independently hydrogen, methyl group, halogen, hydroxy group, methoxy group, acetyl group, propionyl group, nitro group or alkoxy group. The 2-phenyl-6-benzoyl-thiazolo[3,2-b][1,2,4]-triazole derivative has an obvious inhibiting action on acetylcholinesterase, and is used for enhancing memory of patients with dementia and Alzheimer's disease. The invention also discloses a preparation method of the compounds and application of the compounds in preparing drugs for treating senile dementia.
Description
technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to 2-phenyl-6-benzoyl-thiazolo[3,2-b][1,2,4]-triazole derivatives and their preparation methods and as acetylcholine Esterase inhibitors for use in 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 mem...
Claims
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