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Steviol derivative, preparation method thereof and application of steviol derivative in preparation of heart protection medicine

A technique for cardioprotection and steviol, which is applied in the preparation of organic compounds, drug combinations, and carboxylates, etc., can solve problems such as lack of myocardial protection, and achieve protection from death and injury, good cardioprotective activity, and improved cardioprotective activity. Effect

Active Publication Date: 2022-03-29
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that steviol has good anti-cancer effects, including anti-diabetes and anti-cancer effects, but there are few reports on myocardial protection

Method used

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  • Steviol derivative, preparation method thereof and application of steviol derivative in preparation of heart protection medicine
  • Steviol derivative, preparation method thereof and application of steviol derivative in preparation of heart protection medicine
  • Steviol derivative, preparation method thereof and application of steviol derivative in preparation of heart protection medicine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The synthesis of embodiment 1 compound 2-22

[0043] (1) Modifying the cyclopentanol hydroxyl group and 19-COOH of steviol (compound 1) to obtain compounds 2-10 (Table 1);

[0044] ①Modification of cyclopentanol hydroxyl group: use acetic anhydride (Ac 2 O), isovaleric anhydride, propionic anhydride, butyric anhydride, 2-dimethylsuccinic anhydride, succinic anhydride, and phthalic anhydride selectively acylate the hydroxyl group on the cyclopentanol of steviol to obtain compound 2-8 , the specific method is: use acetic anhydride / isovaleric anhydride / propionic anhydride / butyric anhydride / 2-dimethylsuccinic anhydride / succinic anhydride / phthalic anhydride and steviol as reactants, pyridine (Pyr) as binding Acid agent and solvent, 4-dimethylaminopyridine (DMAP) as catalyst, reflux and stir at 100°C for 18 hours to obtain compounds 2-8 respectively.

[0045] ②Modification of 19-COOH: 19-COOH of steviol and allyl bromide (AllylBr), 4-methoxybenzyl chloride (PMBCl) and K 2 ...

Embodiment 2

[0133] A series of compounds obtained in Example 1 were carried out in a zebrafish experiment, the specific method is:

[0134] (1) Zebrafish culture and embryo collection: buy zebrafish (3-12 months old) from the National Zebrafish Resource Center, and flow them under a photoperiod of 14:10 h (light: dark) and a temperature of 28.5 ± 1°C Breeding in a breeding box, feeding with live brine shrimp twice a day; mating of zebrafish (female:male=1:1), collecting embryos, washing with Holt Buffer, and culturing in an incubator (28.5±1°C) 24h, screening by microscopic examination.

[0135] (2) Solution preparation: Dissolve a series of compounds obtained in Example 1 with dimethyl sulfoxide, and add them to the Holt Buffer solution containing DOX (the volume fraction of dimethyl sulfoxide is 0.5%) to obtain the administration group solution ; Dimethyl sulfoxide was directly dissolved in the Holt Buffer solution (dimethyl sulfoxide volume fraction is 0.5%) to obtain a blank group so...

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Abstract

The invention relates to the field of drug design and medicinal chemistry, in particular to a steviol derivative, a preparation method thereof and application of the steviol derivative in preparation of heart protection drugs. The steviol derivative is a compound shown as a formula I or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown as the formula I or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The derivative can effectively treat zebrafish morphological distortion and cardiac insufficiency caused by DOX, protects death and damage of myocardial cells by inhibiting excessive generation of active oxygen and recovering mitochondrial membrane potential, has remarkable heart protection activity, and can be used as a lead compound for treating cardiovascular diseases. Formula I.

Description

technical field [0001] The invention relates to the fields of drug design and medicinal chemistry, in particular to a steviol derivative, its preparation method and its application in the preparation of cardioprotective drugs. Background technique [0002] Cardioprotective drugs can protect the metabolism, structure and function of the heart and blood vessels, and reduce their damage in primary or secondary prevention, and are extremely important in the treatment of patients with cardiovascular disease or high risk of cardiovascular disease. Although including statins, angiotensin-converting enzyme inhibitors (ACEIs), beta-blockers (BBs), angiotensin II type 1 receptor blockers (ARBs) and aldosterone receptor blockers (AIRBs) Several groups of cardioprotective drugs, including , have been shown to be effective in reaching hard endpoints, but treatment of hypertension with these drugs reduces mortality by no more than 30%, and the residual cardiovascular risk is still quite h...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C69/24C07C69/34C07C69/40C07C69/80C07C69/757C07C67/08C07C51/367C07C62/14A61K31/22A61K31/225A61K31/235A61K31/215A61K31/19A61P9/00
CPCC07C69/145C07C69/24C07C69/34C07C69/40C07C69/80C07C69/757C07C67/08C07C51/367C07C62/14A61P9/00C07C2603/86Y02P20/55
Inventor 赵昱徐超
Owner GUANGDONG UNIV OF TECH
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