3-acylamino-N-arylbenzamide compound and application thereof

An aryl benzamide and amide-based technology, applied in the field of medicine, can solve problems such as sequelae, achieve good therapeutic effects, inhibit the level of epileptic seizures, and prolong the effect of seizure latency

Pending Publication Date: 2021-11-30
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therapies such as surgical resection of lesions can only be effective for some patients, and there is a high possibility of sequelae

Method used

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  • 3-acylamino-N-arylbenzamide compound and application thereof
  • 3-acylamino-N-arylbenzamide compound and application thereof
  • 3-acylamino-N-arylbenzamide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0147] Example 1 3-(3-(furan-2-carboxamido)benzamido)methyl phenylacetate

[0148]

[0149] Step A: Add 3-nitrobenzaldehyde (2) (3.02 g, 20 mmol) into a 100 ml one-necked bottle, and add 20 ml of methanol to dissolve it. The reaction solution was cooled to below 0°C, and sodium borohydride (2.27g, 60mmol) was added in batches, and reacted at 0°C for 10min after the addition was complete. After the reaction, the methanol was removed under reduced pressure, the residue was added with water and extracted three times with 20ml ethyl acetate, the organic phase was washed three times with 10mL saturated brine, the organic phase was dried with anhydrous sodium sulfate and the ethyl acetate was removed under reduced pressure to obtain a colorless The oily 3-nitrobenzyl alcohol (3) is directly subjected to the next reaction.

[0150] Step B: Add the 3-nitrobenzyl alcohol (3) obtained in Step A into a 100ml one-necked bottle, and add 30ml of dichloromethane to dissolve it. The reac...

Embodiment 2

[0157] Example 2 Methyl 3-(3-(thiophene-2-carboxamido)benzamido)phenylacetate

[0158]

[0159] Compound 1b NMR data 1 HNMR (400MHz, DMSO-d 6 )δ10.45(s,1H),10.30(s,1H),8.25(s,1H),8.08(s,1H),8.00(d,J=8.0Hz,1H),7.89(d,J=4.8 Hz, 1H), 7.70(m, 3H), 7.52(t, J=8.0Hz, 1H), 7.31(t, J=7.6Hz, 1H), 7.25(t, J=3.2Hz, 1H), 7.01( d,J=7.6Hz,1H),3.69(s,2H),3.63(s,3H); 13 CNMR (100MHz, DMSO-d 6 )δ171.5,165.5,160.0,139.9,139.2,138.9,135.6,134.8,132.1,129.3,128.7,128.6,128.2,124.7,123.3,122.7,121.1,119.9,118.9,51.7,zIMS.4: =395[M+H + ].

Embodiment 3

[0160] Example 3 Methyl 3-(3-(5-chlorothiophene-2-carboxamido)benzamido)phenylacetate

[0161]

[0162] Compound 1c NMR data 1 HNMR (600MHz, DMSO-d 6 )δ10.50(s,1H),10.28(s,1H),8.21(s,1H),7.96(s,2H),7.69(s,3H),7.50(s,1H),7.28(m,2H ),7.00(s,1H),3.64(m,5H); 13 CNMR (150MHz, DMSO-d 6 )δ172.01,165.86,159.47,139.69,139.38,139.08,136.11,135.25,134.69,129.82,129.26,129.12,128.84,125.24,123.78,123.41,121.62,120.39,119.46,52.20,40.84;ESI-MS:m / z =430[M+H + ].

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PUM

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Abstract

The invention provides a 3-acylamino-N-arylbenzamide compound and a pharmaceutically acceptable salt and application thereof. Experiments prove that the compound provided by the invention can remarkably prolong the epileptic seizure latent time induced by pentylenetetrazole and reduce the epileptic seizure grade and death rate; and the epileptic seizure threshold value induced by the maximum electroshock can be obviously increased, and the death rate is reduced. The raw materials required for synthesis of the compound are easy to obtain, the operation is simple and convenient, the process amplification is strong, the compound is suitable for industrial production, and a new medicine is provided for epilepsy treatment. The structures of the general formulas I, II, III, IV and V are respectively shown in the specification.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a 3-amido-N-aryl benzamide compound and its pharmaceutically acceptable salt and medical application, especially the application in antiepileptic drugs. Background technique [0002] Epilepsy (epilepsy) is a common clinical nervous system disease, and its incidence rate is about 1%. At present, there are about 70 million epilepsy patients in the world, and there are more than 10 million epilepsy patients in China. Epilepsy is characterized by epileptic seizures caused by abnormally synchronized discharge of neurons in the brain. If the seizures are not controlled, it will cause serious harm to the patient's quality of life and even life safety. [0003] Drugs are currently used clinically to control epileptic seizures. Traditional antiepileptic drugs mainly act on ion channels on neurons or γ-aminobutyric acid receptors to reduce the excitability in the brain, but about one...

Claims

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Application Information

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IPC IPC(8): C07D307/68C07D333/38C07D409/06C07D405/06C07D333/34A61P25/08
CPCC07D307/68C07D333/38C07D409/06C07D405/06C07D333/34A61P25/08
Inventor 崔孙良徐束恒陈忠汪仪徐层林
Owner ZHEJIANG UNIV
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