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A hydrogen sulfide donor and its preparation method and use

A technology of hydrogen sulfide and donor, which is applied in the field of medicine, can solve the problems of being easily oxidized and deteriorated, uncontrollable dosage, easy to volatilize, etc., and achieve the effect of reducing endoplasmic reticulum stress

Active Publication Date: 2021-06-29
GUANGZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

They release endogenous hydrogen sulfide through cystathionine-β-synthase (CBS) to exert a protective effect on ischemic stroke, but they have a short t1 / 2 in vivo and are volatile, making it uncontrollable to administer amount, and due to the presence of amino groups in the compound structure, it is easily oxidized and deteriorated in the air

Method used

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  • A hydrogen sulfide donor and its preparation method and use
  • A hydrogen sulfide donor and its preparation method and use
  • A hydrogen sulfide donor and its preparation method and use

Examples

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Embodiment 1

[0050] The present embodiment is the donor (MTC) of hydrogen sulfide according to the present invention, and its structural formula is as shown in formula (I):

[0051]

[0052] The preparation method of the donor (MTC) of above-mentioned hydrogen sulfide, comprises the steps:

[0053] (1) Dissolve 1mmol of the compound shown in formula (II) in 40mmol of thionyl chloride (SOCl 2 ), reflux the reaction (rf) at 70°C until complete, track the reaction to the end by thin-layer chromatography, spin down the solvent under reduced pressure, and obtain the compound shown in the intermediate product formula (Ⅲ);

[0054] (2) Dissolve 1mmol of the compound represented by formula (III) described in step (1) in 45mmol of dichloromethane (DCM), then add 2mmol of triethylamine (TEA) and stir the reaction for 10min under ice-bath conditions, then add 1mmol of the compound shown in formula (Ⅳ), continue to stir until the end of the reaction, spin the solvent to dryness under reduced press...

Embodiment 2

[0060] The present embodiment is the donor (MTC) of hydrogen sulfide according to the present invention, and its structural formula is as shown in formula (I):

[0061]

[0062] The preparation method of the donor (MTC) of above-mentioned hydrogen sulfide, comprises the steps:

[0063] (1) Dissolve 1 mmol of the compound shown in formula (II) in 45 mmol of thionyl chloride (SOCl 2 ), reflux the reaction (rf) at 80°C until complete, track the reaction to the end by thin-layer chromatography, spin the solvent under reduced pressure, and obtain the compound shown in the intermediate product formula (Ⅲ);

[0064] (2) Dissolve 1mmol of the compound shown in formula (III) described in step (1) in 50mmol of dichloromethane (DCM), then add 3mmol of triethylamine (TEA) and stir the reaction for 30min under ice-bath conditions, then add 1mmol of the compound shown in formula (Ⅳ), continue to stir until the end of the reaction, spin the solvent to dryness under reduced pressure, and ...

Embodiment 3

[0068] The present embodiment is the donor (MTC) of hydrogen sulfide according to the present invention, and its structural formula is as shown in formula (I):

[0069]

[0070] The preparation method of the donor (MTC) of above-mentioned hydrogen sulfide, comprises the steps:

[0071] (1) Dissolve 1 mmol of the compound shown in formula (II) in 43 mmol of thionyl chloride (SOCl 2 ), reflux the reaction (rf) at 75°C until complete, track the reaction to the end by thin-layer chromatography, spin the solvent under reduced pressure, and obtain the compound shown in the intermediate product formula (Ⅲ);

[0072] (2) Dissolve 1mmol of the compound shown in formula (III) described in step (1) in 48mmol of dichloromethane (DCM), then add 2.5mmol of triethylamine (TEA) and stir the reaction for 20min under ice-bath conditions, then Add the compound represented by the formula 1mmol (IV), continue to stir until the reaction is completed, spin the solvent under reduced pressure, and...

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Abstract

The invention relates to a donor of hydrogen sulfide and its preparation method and application, belonging to the technical field of medicine. The donor of hydrogen sulfide provided by the present invention has a chemical name of S-(4-fluorobenzyl)-N-(3,4,5-trimethoxybenzoyl)-L-cysteine ​​methyl ester, The chemical structural formula is shown in formula (I); the hydrogen sulfide donor (MTC) provided by the present invention can effectively treat the disease of ischemic stroke by activating the PI3K / AKT pathway, inhibiting the mitochondrial apoptosis signaling pathway, and reducing the internal To achieve the purpose of effective treatment of ischemic stroke, there are various therapeutic targets such as cytoplasmic reticulum stress, activation of ERK-MEK signaling pathway, increase of survival rate of nerve cells or protection of neurons from ischemic injury.

Description

technical field [0001] The invention relates to a donor of hydrogen sulfide and its preparation method and application, belonging to the technical field of medicine. Background technique [0002] Cerebral infarction, also known as ischemic stroke, is caused by various causes of local brain tissue blood supply disturbance, resulting in ischemic brain damage, activating a series of cascade reactions in cells, including various signaling pathways, and eventually Cause irreversible brain tissue damage. At present, the most effective method for the clinical treatment of stroke is to quickly unblock its reperfusion, that is, ischemia-reperfusion. / reperfusion injury. At present, there are beta-receptor blockers, calcium ion antagonists, statins, RAS blockers, etc. in the clinical treatment of cerebral ischemia, but the therapeutic target is relatively single, and side effects such as gastrointestinal bleeding. Some antioxidant drugs, hormones, and specific calcium channel bloc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/25C07C319/20A61P9/10A61P25/00A61K31/216
CPCA61P9/10A61P25/00C07C323/25
Inventor 陈鲲樊静程魁张中伟胡滨雁陈韵帆胡佳钦秦嘉裕李海鹏
Owner GUANGZHOU UNIVERSITY
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