Hydrogen sulfide donor type compound containing 1,2-dithiole-3-thioketone structure and blood fat reducing application thereof

A technology of dithiocyclopentene and compound, applied in the field of biomedicine, can solve problems such as reduction, and achieve the effects of reducing TG and TC, significantly resisting lipid peroxidation, and improving antioxidant capacity

Inactive Publication Date: 2018-11-23
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Studies have shown that the content of hydrogen sulfide in patients with hyperlipidemia, hypertension and hyperglycemia is significantly reduced, and exogenous supplementation of hydrogen sulfide has positive significance for improving the above-mentioned various neovascular-related pathological processes. In addition, the existing hydrogen sulfide supply Body shape drugs are often used to treat diseases such as inflammation, oxidative stress and cancer, but there are few reports on the treatment of cardiovascular and cerebrovascular diseases such as hyperlipidemia

Method used

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  • Hydrogen sulfide donor type compound containing 1,2-dithiole-3-thioketone structure and blood fat reducing application thereof
  • Hydrogen sulfide donor type compound containing 1,2-dithiole-3-thioketone structure and blood fat reducing application thereof
  • Hydrogen sulfide donor type compound containing 1,2-dithiole-3-thioketone structure and blood fat reducing application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 5-[4-(1,2-Dithiocyclopentene-3-thione-5-yl)phenoxy)]pentanoic acid ethyl ester (ethyl5-(4-(3-thioxo-3H-1,2 -dithiol-5-yl)phenoxy)pentanoate, 1) synthesis:

[0041]

[0042] 5-(4-hydroxyphenyl)-1,2-dithiocyclopentene-3-thione (0.50g, 2.21mmol), potassium carbonate (0.92g, 6.65mmol), potassium iodide (0.20g, 1.20mmol ) was dissolved in N,N-dimethylformamide (30mL), ethyl 5-bromopentanoate (0.70g, 3.32mmol) was added, and heated to reflux for 4h. After the reaction was completed, it was suction filtered, extracted, and concentrated. Column chromatography separation (developing solvent: petroleum ether / ethyl acetate = 8 / 1) to obtain the target product 5-[4-(1,2-dithiocyclopentene-3-thione-5-yl)phenoxy )] Ethyl valerate, 0.5 g of a yellow solid with a special smell, the yield is 63.8%, m.p.84.0°C-86.0°C.

[0043] ESI-MS: Calcd. For C 16 h 18 o 3 S 3 [M+Na] + :377.0,Found:377.0

[0044] NMR spectrogram data: 1 H NMR (400MHz, DMSO-d 6 )δ: 7.88~7.84(m, 2H, ArH), 7....

Embodiment 2

[0047] Acute lipid-lowering animal experiment of compound 1.

[0048]The pharmacodynamics of compound 1 of the present invention is achieved by the hypolipidemic effect of compound 1 on the acute hyperlipidemia model in mice induced by Triton WR-1339.

[0049] The specific operation steps are as follows:

[0050] 1. Experimental materials

[0051] Materials: Triton WR-1339 (Sigma, USA), fenofibrate (Wuhan Hongrui Reagent Co., Ltd.), compound 1 (self-made in the laboratory).

[0052] Animals: Kunming mice (20.0±2.0g).

[0053] 2. Experimental methods and results

[0054] Mouse model of acute hyperlipidemia

[0055] The mice were fed adaptively for 3 days, and randomly divided into 4 groups (normal group, model group, compound 1 group and fenofibrate group) with 10 mice in each group: ① blank group, given 0.5% CMC-Na solution by intragastric administration; ② model group group, 0.5% CMC-Na solution was administered by intragastric administration; ③ compound 1 group, intraga...

Embodiment 3

[0063] Chronic lipid-lowering animal experiment of compound 1.

[0064] The pharmacodynamics of the compound 1 of the present invention is realized by the hypolipidemic effect of the compound 1 on the mouse chronic hyperlipidemia model induced by high-fat feed feeding.

[0065] The specific operation steps are as follows:

[0066] 1. Experimental materials

[0067] Materials: high-fat feed (self-made in the laboratory), fenofibrate (Wuhan Hongrui Reagent Co., Ltd.), compound 1 (self-made in the laboratory).

[0068] Animals: Kunming mice (20.0±2.0g).

[0069] 2. Experimental methods and results

[0070] Mouse Model of Chronic Hyperlipidemia

[0071] After the mice were fed for 3 days to adapt to the environment, 12 mice were randomly selected as the normal group and 36 mice as the high-fat diet group. The normal group was given normal diet and the high-fat diet group was fed with high-fat diet. After the mice were fed for 5 weeks, the orbital blood was collected to measur...

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Abstract

The invention discloses a hydrogen sulfide donor type compound containing a 1,2-dithiole-3-thioketone structure and blood fat reducing application thereof, and belongs to the technical field of biological medicines. The compound is similar with Fibrates drugs in structure, can reduce level of triglyceride and cholesterol, and has the effect of being broad in spectrum and reducing blood fat. Besides, the compound can slowly release hydrogen sulfide to bring multiple cardiovascular protection effects such as oxidative stress resistance, oxidation resistance improvement and the anti-inflammationeffect into play.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, relates to a hydrogen sulfide donor type aryloxyalkanoic acid and its ester compounds, in particular to a class of hydrogen sulfide donor type compounds containing 1,2-dithiocyclopentene-3-thione structure and Its hypolipidemic application. Background technique [0002] Cardiovascular and cerebrovascular diseases have become the main diseases that endanger human health, and dyslipidemia is closely related to the high incidence of cardiovascular and cerebrovascular diseases. Dyslipidemia, also known as hyperlipidemia, is a variety of causes of lipid metabolism disorders that lead to elevated plasma total cholesterol (TC), triglycerides (TG), low-density lipoprotein cholesterol (LDL-C) and (or) High-density lipoprotein cholesterol (HDL-C) is too low. Clinically, hyperlipidemia is simply divided into the following four categories: ① hypercholesterolemia: pure TC level increases; ② hypertriglyc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04A61P3/06A61P29/00A61P39/06
CPCA61P3/06A61P29/00A61P39/06C07D339/04
Inventor 边晓丽陈子章谢允东许艳红邵丽花王秋棠
Owner XI AN JIAOTONG UNIV
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