Hydrogen sulfide donor, preparation method and applications thereof

A hydrogen sulfide and donor technology, applied in the field of medicine, can solve the problems of easy oxidative deterioration, volatile, uncontrollable dosage, etc., and achieve the effects of reducing endoplasmic reticulum stress, increasing survival rate, and activating signaling pathways

Active Publication Date: 2020-02-11
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 ar...

Method used

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  • Hydrogen sulfide donor, preparation method and applications thereof
  • Hydrogen sulfide donor, preparation method and applications thereof
  • Hydrogen sulfide donor, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
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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 hydrogen sulfide donor, a preparation method and applications thereof, and belongs to the technical field of medicines, wherein the hydrogen sulfide donor is chemically named S-(4-fluorobenzyl)-N-(3,4,5-trimethoxybenzoyl)-L-cysteine methyl ester, and has a chemical structural formula represented by a formula (I). According to the invention, the hydrogen sulfide donor (MTC) can effectively treat cerebral arterial thrombosis diseases by activating a PI3K/AKT pathway, inhibiting a mitochondrial apoptosis signal pathway, reducing endoplasmic reticulum stress, activatingan ERK-MEK signal pathway, increasing the survival rate of nerve cells or protecting various treatment targets of nerve cell 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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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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