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A kind of benzoic acid thioester compound and its application
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A technology of benzoic acid thioester and compound, which is applied in the field of benzoic acid thioester compounds, can solve the problems of inability to pass through the blood-brain barrier, large molecular weight, and difficulty in large-scale preparation, so as to prevent and treat neurodegenerative diseases and improve cognitive function. Knowledge, high activity effect
Active Publication Date: 2017-07-25
ZHEJIANG UNIV
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However, NGF is a protein composed of more than 100 amino acids; due to reasons such as large molecular weight and strong polarity, it cannot pass through the blood-brain barrier, and it is difficult to prepare on a large scale, which limits its actual clinical application.
At present, no better treatment method has been found other than direct administration of drugs in brain surgery
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[0045] Dissolve n-hexanethiol (1.18g, 10.0mmol) in dry 100ml of dichloromethane, add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (3.83g, 20.0mmol ), 2,3-dihydroxybenzoic acid (1.54g, 10.0mmol), react overnight at room temperature. TLC (n-hexane / ethyl acetate=6 / 1) detected the reaction, filtered, evaporated the solvent under reduced pressure, and silica gel column chromatography (developing solvent: petroleum ether / ethyl acetate=50 / 1) gave 252 mg of a colorless liquid, Yield 10%.
[0046] 1 H NMR (500MHz, CDCl 3 ): δ11.26(s, 1H), 7.42(d, 1H, J=8.0Hz), 7.10(d, 1H, J=8.0Hz), 6.81(t, 1H, J=8.0Hz), 5.69(s ,1H),3.07(t,2H,J=7.0Hz),1.68(m,2H),1.44(m,2H),1.33-1.31(m,4H),0.90(t,3H,J=7.0Hz) .HRMS(ESI)m / z calcd for C 13 h 19 o 3 S + [M+H] + 255.1049, Found 255.1048.
[0047] The structural formula of this compound is:
[0080] Identification of biological activity: In the animal model of Alzheimer's disease, studies have found that NGF can prevent or reduce the degeneration of neurons, prevent the progression of AD to a certain extent, and have the effects of promoting nerve growth and neuroprotection. Because PC12 cells have the general characteristics of nerve cells, PC12 cells will stop dividing under the action of NGF, grow protrusions, and transform into neuron-like cells. Therefore, the compound that can cause PC12 cells to transform into neuron-like cells has application value in the prevention and treatment of senile dementia.
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Abstract
The invention discloses a thiobenzoate compound and a use thereof. The thiobenzoate compound has a general structural formula (I). In the formula (I), R represents C1-C30 alkyl, R1-R5 represent hydrogen, hydroxyl, ester group, amino group or amido group, and at least two adjacent substituents of R1-R5 are hydroxyl groups. The invention also provides a use of the thiobenzoate compound in preparation of drugs and foods for preventing and treating neurodegenerative diseases and improving perceiving and learning memory capability. The thiobenzoate compound with a novel structure form has substantial nerve growth factor-like activity and high activity and can be used in preparation of drugs and foods for preventing and treating neurodegenerative diseases and improving perceiving and learning memory capability.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a benzoic acid thioester compound and its application in the preparation of foods and medicines for preventing and treating neurodegenerative diseases and improving cognition, learning and memory. Background technique [0002] With the rapid development of economy and society, the great improvement of human living standards and medical and health care, the prolongation of human life, the gradual acceleration of the aging process, and the increasingly serious phenomenon of social aging. With the acceleration of the aging process, the prevalence of senile dementia has also increased significantly, and it has become the fourth leading cause of death in adults, second only to heart disease, cancer, and stroke, and has become a serious threat to the health of the elderly. Obstinate disease. According to statistics, the prevalence rate of people over 65 years old...
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