2‑Phenyl‑6‑benzoyl‑thiazolo[3,2‑b][1,2,4]‑triazole derivatives and their applications

A technology of benzoyl and thiazolo, which is applied in the field of medicine and can solve problems such as drug resistance or pharmacokinetic defects

Inactive Publication Date: 2017-06-23
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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  • 2‑Phenyl‑6‑benzoyl‑thiazolo[3,2‑b][1,2,4]‑triazole derivatives and their applications
  • 2‑Phenyl‑6‑benzoyl‑thiazolo[3,2‑b][1,2,4]‑triazole derivatives and their applications
  • 2‑Phenyl‑6‑benzoyl‑thiazolo[3,2‑b][1,2,4]‑triazole derivatives and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0021] In a 250 mL three-necked flask, add 0.1 mol of thiosemicarbazide and 100 mL of dichloromethane, stir and dissolve in an ice-water bath, and then add 0.13 mol of pyridine. 0.13mol of 4-fluorobenzoyl chloride was slowly added dropwise at 0-5 °C, the dropwise addition was completed in 20 min, and the reaction was performed at 15 °C for 2 h to complete the reaction. A large amount of white solid appeared in the system, which was filtered. The obtained white solid was dissolved in 80 mL of sodium hydroxide solution with a mass fraction of 5%, heated to reflux for 2 h, lowered to room temperature, and adjusted to pH 5-6 with a mass fraction of 3.65% of dilute hydrochloric acid, a large amount of light yellow solid was precipitated, filtered , recrystallized to give 5-(4-fluorophenyl)-3-mercapto-1,2,4-triazole 17.2 g, 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 were obtained 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 of Example 1, 5-{4- [2-(1-Piperidinyl)ethoxy]phenyl}-3-mercapto-1,2,4-triazole 24.3 g, yield 79.9%, ESI-MS (m / z): 305.1 ( M+H) + .

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Abstract

The invention discloses 2-phenyl-6-benzoyl-thiazolo[3,2-b][1,2,4]-triazole derivatives of general formula I or pharmaceutically acceptable hydrates thereof , salts, including stereoisomers or tautomers thereof, R1 and R2 in formula I are independently hydrogen, methyl, halogen, hydroxyl, methoxy, acetyl, propionyl, nitro or alkane Oxygen. The 2-phenyl-6-benzoyl-thiazolo[3,2-b][1,2,4]-triazole derivatives of the present invention have obvious inhibitory effect on acetylcholinesterase, and are used to enhance Memory in patients with dementia and Alzheimer's disease. 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, and in particular relates to 2-phenyl-6-benzoyl-thiazolo[3,2-b][1,2,4]-triazole derivatives and a preparation method thereof and 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 with this disease show marked declines 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 can be used to improve memory in Alzheimer's disease patients. By inhibiting acetylcholinesterase, the compounds increase levels of the neurotransmitter acetylcholine in the brain, thereby enhancing memory. [0004] Exi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04A61K31/429A61K31/454A61P25/28
CPCC07D513/04
Inventor 刘斯婕雷霓张宝华史兰香郭瑞霞
Owner SHIJIAZHUANG UNIVERSITY
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