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Application of (z)-2-imino-5-(3,5-dimethoxybenzyl)-1-methylimidazolidine-4-one in the preparation of cardiovascular drugs

A technology of dimethoxybenzyl and methylimidazolidine, which is applied in the application field of medicine

Active Publication Date: 2018-01-19
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of the above situation, the object of the present invention is to provide a kind of imidazolidine compound containing multiple substituents in the preparation of cardiovascular drugs, so as to solve the defects of existing drugs

Method used

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  • Application of (z)-2-imino-5-(3,5-dimethoxybenzyl)-1-methylimidazolidine-4-one in the preparation of cardiovascular drugs
  • Application of (z)-2-imino-5-(3,5-dimethoxybenzyl)-1-methylimidazolidine-4-one in the preparation of cardiovascular drugs
  • Application of (z)-2-imino-5-(3,5-dimethoxybenzyl)-1-methylimidazolidine-4-one in the preparation of cardiovascular drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Preparation of (Z)-2-imino-5-(3,5-dimethoxybenzylidene)-1-methylimidazolidin-4-one (compound IV5).

[0022]

[0023] 3,5-Dimethoxybenzaldehyde (0.83g, 5mmol), creatinine (0.57g, 5mmol), molten sodium acetate (2.05g, 25mmol) and glacial acetic acid (7mL) were stirred under reflux for 10h, cooled After reaching room temperature, 5 mL of water was added, suction filtered, washed with water, and recrystallized with DMF and water to obtain 1.09 g of dark yellow-brown crystals (Compound IV5), with a yield of 84.2%. The physical and chemical identification results are as follows:

[0024] mp: 222~223°C;

[0025] IR (KBr, cm -1 ): 3287, 2999, 2842, 1703, 1660, 1588, 1558, 1505, 1458;

[0026] 1 H-NMR (400MHz, DMSO-d 6 ): δ (ppm) 3.17 (s, 3H, CH 3 ), 3.79 (s, 6H,CH 3 ), 6.139 (s, 1H, =CH), 6.216 (s, 1H, Ar), 7.58 (s, 2H, ArH);

[0027] HR-MS: C 13 h 15 N 3 o 3 Theoretical value: 261.1113, actual value: 261.1111.

Embodiment 2

[0028] Example 2: The protective effect of compound IV5 on primary cardiomyocytes cultured in vitro against glucose-hypoxia / reperfusion injury.

[0029] Rat primary cardiomyocytes were cultured for 72 hours, and randomly divided into non-glucose hypoxia / reoxygenation control group ( figure 1 denoted as "normal" in the group), non-glucose hypoxia / reoxygenation + IV5 group ( figure 1 expressed as "IV5" in , where the doses of IV5 were 0.1, 1, and 10 μM), the glucose-deficient hypoxia / re-oxygenation group ( figure 2 denoted as "OGD / R") and glucose hypoxia / reoxygenation+IV5 group ( figure 2 Expressed as "OGD / R+IV5", where the dosage of IV5 is 0.1, 1, 10 μM respectively). Treat with hypoxia and glucose for 3 hours, then replace the medium with normal glucose and reoxygenate for 12 hours, use the LDH method to detect the degree of cell damage, and calculate the leakage rate of lactate dehydrogenase (LDH) according to the following formula (%) = A 培养液 / (A 培养液 +A 细胞均浆液 ) × 100%...

Embodiment 3

[0032] Example 3: Protective effect of compound IV5 on myocardial ischemia / reperfusion injury in rats.

[0033] Male SD rats were randomly divided into control group (sham operation group, image 3 Indicated as "CON"), model group, high-, medium-, and low-dose IV5 groups (the dosage of IV5 was 4 mg / kg, 2 mg / kg, and 1 mg / kg, respectively), 10 rats in each group. Myocardial ischemia model in rats was made by ligating the left anterior descending coronary artery. After 30 minutes of ischemia, the rats were reperfused. Immediately after reperfusion, IV5 was injected into the common jugular vein with different doses and equal volumes. The effect of IV5 on left ventricular infarct volume was observed by TTC staining.

[0034] image 3 shows the effect of compound IV5 on reducing the infarct volume of rat left ventricle (mean±SD, n=10; compared with model group, **p<0.01). It can be known that compound IV5 has a protective effect on myocardial ischemia / reperfusion injury in rats.

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Abstract

The invention discloses the application of (Z)-2-imino-5-(3,5-dimethoxybenzylidene)-1-methylimidazolidin-4-ketone in preparing cardiovascular medicine. Specifically, the compounds of the present invention have significant protective effects on myocardial ischemia / reperfusion injury, can significantly reduce the volume of left ventricular infarction in rats with myocardial ischemia, and are suitable for preparation for the prevention and / or treatment of cardiovascular diseases (especially ischemic cardiomyopathy, myocardial ischemia / reperfusion injury and other conditions).

Description

technical field [0001] The invention relates to the field of medicine, and relates to the preparation of (Z)-2-imino-5-(3,5-dimethoxybenzyl)-1-methylimidazolidin-4-one for preventing and / or Or the application in the medicine of treating cardiovascular disease. Background technique [0002] In recent years. With the advancement of shock treatment and the establishment and promotion of methods such as arterial bypass surgery, thrombolytic therapy, percutaneous transluminal coronary angioplasty, extracorporeal circulation in cardiac surgery, cardiopulmonary cerebral resuscitation, replantation of severed limbs, and organ transplantation, the Many tissues and organs can be reperfused with blood after ischemia. In most cases, reperfusion after ischemia can restore tissue and organ functions, repair damaged structures, and improve the patient's condition. But sometimes reperfusion after ischemia not only fails to restore the function of tissues and organs, but aggravates the dy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/4168A61P9/00A61P9/10
Inventor 张慧灵敖桂珍赵雯洁王琛
Owner SUZHOU UNIV
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