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Hirsutine analogue and application thereof in preparation of anti-hypertensive drugs

A technique for rhynchophylline and antihypertensive, which is applied to the structure, preparation, and preparation of rhynchophylline analogs of Chinese herb Uncaria chinensis, can solve the problems of low safety, speed up and the like, and achieve significant Antihypertensive effect

Inactive Publication Date: 2015-10-14
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the quick-acting antihypertensive drugs commonly used in clinical practice, such as nifedipine, mostly have side effects of accelerating heart rate and low safety.

Method used

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  • Hirsutine analogue and application thereof in preparation of anti-hypertensive drugs
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  • Hirsutine analogue and application thereof in preparation of anti-hypertensive drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Preparation of rhynchophylline analogues of formula (1) structure

[0030] 1. Preparation of N-tert-butyloxycarbonyl-S-propargyl-cysteine ​​(SPRC-Boc)

[0031]

[0032] Take S-propargyl-cysteine ​​(1.59g, 10mmol) and dissolve in the mixed solution (50ml / 50ml) of tetrahydrofuran and water, add (Boc) 2 O (3.27g, 15mmol) and triethylamine (2.79ml, 20mmol), stirred at room temperature for 12 hours, TLC monitored the reaction, potassium permanganate chromogen developed color, after the reaction was complete, the tetrahydrofuran was decompressed, and then the remaining reaction solution Diethyl ether was extracted three times, the aqueous layer was adjusted to Ph=2 with 1N HCl, extracted three times with ethyl acetate, the organic phase was combined, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter and spin dry to obtain a brown oily substance that is directly used as a reaction material;

[0033] 2. Preparation of compound (2)

[0034] ...

Embodiment 2

[0040] Embodiment 2 pharmacological action experiment

[0041] The rhynchophylline analog shown in structure (1) reduces the blood pressure and the heart rate level experiment of SHR rat:

[0042] Thirty-two 16-week-old inbred SHR rats were divided into four groups, 8 in each group, administered according to the following scheme, and the changes in blood pressure of the rats within 1 hour after administration were recorded:

[0043](1) SHR control group: SHR rats were given ethanol solution (400 microliters per kilogram of body weight) through the tail vein;

[0044] (2) 5mg / kg group: SHR rats were given ethanol solution of rhynchophylline analogues as shown in the above structure (1) through the tail vein (400 microliters per kilogram of body weight, containing 5 mg of analogues per 400 microliters) ;

[0045] (3) 10mg / kg group: SHR rats were given the ethanol solution of rhynchophylline analogues as shown in the above structure (1) through the tail vein (400 microliters pe...

Embodiment 3

[0049] Example 3 In Vitro Vascular Ring Experiment

[0050] The SD rats were anesthetized by intraperitoneal injection of chloral hydrate (20 mg / kg) and killed by neck dislocation. The thorax was cut open, and the complete thoracic aorta was taken out and placed in PSS nutrient solution with oxygen to strip the connective tissue and fat outside the blood vessel. The blood vessel was made into a 3mm vascular ring, which was placed in 37-degree oxygenated PSS nutrient solution, and connected to the tension transducer of the SUMC-PC biological signal processor (Shanghai Jialong Jiaoyi Factory) through a stainless steel triangle hook. Record the vasoconstriction tension, stimulate the blood vessels with norepinephrine and relax them with acetylcholine to prove the integrity of the vascular endothelium, then wash and change the fluid, stimulate the vasoconstriction with phenylephrine to reach a plateau, then add Y482 in order from low to high concentration, and draw the volume Effe...

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Abstract

The invention belongs to the field of traditional Chinese medicine production and relates to a traditional Chinese medicine uncaria extract, namely hirsutine analogue compound with the structure represented by formula (1) and application of the hirsutine analogue compound in the preparation of anti-hypertensive drugs. An experiment proves that the hirsutine analogue compound has remarkable pharmacological actions of resisting hypertension and vascular dilation. A spontaneously hypertensive rat (SHR) experiment proves that the blood pressure and the heart rate of an SHR are obviously decreased after 30 minutes of administration, and the blood pressure of the spontaneously hypertensive rat can be rapidly and effectively decreased; an in-vitro vascular ring vasomotion experiment proves that by virtue of an extremely low dose of the hirsutine analogue compound, the vascular ring contraction caused by phenylephrine can be remarkably dilated. The hirsutine analogue compound can be used as a raw material of a pharmaceutical preparation, is further used for preparing drugs for treating hypertension and is particularly used for preparing vascular dilation drugs for treating hypertensive emergencies.

Description

technical field [0001] The invention belongs to the field of traditional Chinese medicine pharmacy, and relates to the structure, preparation and application of rhynchophylline analogues of Uncaria uncaria extracts from traditional Chinese medicines in the preparation of antihypertensive drugs. Background technique [0002] Hypertensive emergency refers to patients with primary or secondary hypertension, under the action of certain inducements, the blood pressure suddenly and significantly increases (generally exceeding 180 / 120mmH g ), a severe life-threatening clinical syndrome accompanied by progressive acute damage to important target organ functions such as the heart, brain, and kidneys. Hypertensive emergencies include hypertensive encephalopathy, intracranial hemorrhage, cerebral infarction, acute heart failure, pulmonary edema, acute coronary syndrome, aortic dissection, eclampsia, etc. Malignant hypertension, hypertensive crisis, etc. all belong to this category. C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14A61P9/12A61P9/08A61P9/10
CPCY02P20/55C07D471/14
Inventor 朱依谆朱恺杨素娜古险峰朱依纯
Owner FUDAN UNIV
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