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1-benzhydryl-4-methyl piperazine type compound, and preparation method and application thereof

A compound and composition technology, applied in the field of medicine, can solve the problems of neuroprotective agents such as weak clinical efficacy, failure to show expected effect, and limitation of clinical application, so as to reduce brain tissue cell apoptosis and improve neurobehavioral function , the effect of increasing integrity

Active Publication Date: 2017-06-20
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the past, some drugs and small molecule compounds were developed for different links in the cascade reaction induced by cerebral ischemia. Although the results of preclinical basic research were effective, they did not show the expected effect when entering clinical trials.
The clinical efficacy of some neuroprotective agents is not strong, and they also have relatively large toxic and side effects, which limits clinical application

Method used

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  • 1-benzhydryl-4-methyl piperazine type compound, and preparation method and application thereof
  • 1-benzhydryl-4-methyl piperazine type compound, and preparation method and application thereof
  • 1-benzhydryl-4-methyl piperazine type compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: Preparation of 1-benzhydryl-4-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)piperazine (I-1), its structural formula as follows:

[0048]

[0049] Step 1) 1-Benzhydryl-4-(prop-2-yn-1-yl)piperazine

[0050] Put 0.50g (2.0mmol) of 1-benzhydrylpiperazine, 0.55 (4.0mmol) of potassium carbonate and 5mL of N,N-dimethylformamide (DMF) into a 50mL eggplant-shaped bottle, slowly drop Add 0.28g (2.4mmol) propyne bromide, stir for 0.5h, move to room temperature and react for 12h, quench the reaction solution with water, extract 3 times with ethyl acetate, combine the organic phases, wash 2 times with saturated sodium chloride solution, no Dry over sodium sulfate, filter, and concentrate under reduced pressure. The residue is subjected to column chromatography (petroleum ether: ethyl acetate = 5:1) to obtain a white solid weighing 0.31 g, yield: 54%.

[0051] 1H NMR (300MHz, DMSO-d6) δ7.43–7.41(m,4H),7.31–7.26(m,4H),7.19–7.15(m,2H),4.24(s,1H),3.25(s,2H ),3.17(s,1H),2....

Embodiment 2

[0059] Example 2: Preparation of 1-benzhydryl-4-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)piperazine (I-1).

[0060] In step 1), the molar ratio of 1-benzhydrylpiperazine to 3-bromopropyne and potassium carbonate is 1:1:1; the concentration of 1-benzhydrylpiperazine is 0.1mol / L.

[0061] In step 2), the molar ratio of aniline sodium nitrite to sodium azide is 1:1:1, and the reaction concentration of compound III is 0.5 mol / L; 4 mol / L aqueous hydrochloric acid is used.

[0062] In step 3), the molar ratio of compound III, compound V, sodium ascorbate and copper sulfate is 3:3:1:1, 0.1mol / L; the reaction solvent is methanol and water with a volume ratio of 3:1.

Embodiment 3

[0063] Embodiment 3: Preparation of 1-benzhydryl-4-((1-(3-methylphenyl)-1H-1,2,3-triazol-4-yl)methyl)piperazine (I -2), its structural formula is as follows:

[0064]

[0065] Synthetic steps refer to Example 1, the difference is that the reactant substituent needs to be changed according to the substituent of the target compound;

[0066] MS(ESI)m / z:calculated for C27H29N5[M+H]+:423.2,found:424.2

[0067] 1H NMR (300MHz, DMSO-d6) δ8.65(s,1H),7.76–7.72(m,1H),7.68–7.66(m,1H),7.46–7.37(m,6H),7.28–7.23(m ,5H),7.19–7.12(m,3H),4.24(s,1H),3.65(s,2H),2.48–2.41(m,4H),2.38(s,3H),2.32–2.18(m,4H );

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Abstract

The invention discloses a compound of a structure shown by a formula I and a pharmaceutically acceptable salt or solvent compound thereof, wherein R1, R2, R3 and R4 are respectively and independently selected from H, F, Cl, Br, CN, CF3, OH, NO2, NH2, substituted or non-substituted C1 to C6 alkyls, substituted or non-substituted C1 to C6 alkoxy, substituted or non-substituted C1 to C6 alkyl acyls or substituted or non-substituted C1 to C6 alkyl amido groups. The invention also discloses a preparation method of the pharmaceutically acceptable salt or solvent compound of the compound of the structure shown by the formula I and application of the compound to the preparation of medicines for preventing and treating cerebral arterial thrombosis. The formula I is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a preparation method and application of 1-benzhydryl-4-methylpiperazine compounds. Background technique [0002] Stroke is a sudden-onset cerebral blood circulation disorder disease, and it is currently the second most lethal disease in the world. Its etiology is mainly caused by various factors causing intracerebral artery stenosis, occlusion or rupture, resulting in acute cerebral blood circulation disorder, clinically manifested as symptoms and signs of transient or permanent neurological dysfunction. Stroke mainly includes ischemic stroke and hemorrhagic stroke, and the incidence of ischemic stroke accounts for about 60% to 70% of the total number of stroke patients. It is the current medical research to control the mortality rate of stroke and improve the quality of life. problem to be solved. [0003] At present, the commonly used clinical treatment strategy i...

Claims

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Application Information

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IPC IPC(8): C07D249/06A61K31/496A61P9/10A61P25/00
CPCC07D249/06
Inventor 姚红红张惠斌吴芳芳韩丽张晓田
Owner SOUTHEAST UNIV
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