Diarylmethylene disulfide compound as well as preparation method and application thereof

A technology for compounds and preparations, applied in the field of diarylmethylene disulfide compounds and their preparation, can solve the problems of limited treatment means and great harm of cerebral apoplexy, etc.

Active Publication Date: 2017-11-07
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, in view of the great harm of stroke and the extremely limited current treatment methods, the development of new drugs for the prevention and / or treatment of stroke has always been the focus of extensive attention of frontier scholars in this field, which is of great significance

Method used

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  • Diarylmethylene disulfide compound as well as preparation method and application thereof
  • Diarylmethylene disulfide compound as well as preparation method and application thereof
  • Diarylmethylene disulfide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 1,2-bis[(3,5,6-trimethylpyrazin-2-yl)methyl]disulfide (LYY-Ι 1 )

[0056] 1-bromotetramethylpyrazine (0.210g, 0.97mmol), thiourea (0.111g, 1.45mmol), sodium carbonate (0.154g, 1.45mmol), manganese dioxide (0.084g, 0.97mmol) were added to a 100mL reaction flask , then add wet-PEG200 (20mL) (PEG200:H 2 O=10:1), heated to 40°C, and stirred for 3h. Cool to room temperature, add water (20mL), extract with ethyl acetate (20mL) three times, wash with water (50mL) three times, dry over anhydrous magnesium sulfate, filter with suction, column chromatography [eluent petroleum ether: ethyl acetate (v :v)=10:1], a yellow solid was obtained. Yield 45%. Mp: 73~75℃.

[0057] 1 H NMR (400MHz, CDCl 3 ), δ (ppm): 3.99 (s, 4H, CH 2 ),2.54(s,6H,CH 3 ),2.49(s,12H,CH 3 ).

[0058] 13 C-NMR (600MHz, CDCl 3 ), δ(ppm): 150.17, 148.94, 148.64, 146.61, 42.67, 21.62, 21.40, 21.09.

[0059] HR-MS:[M+H] + , Calcd: 335.1364, Found: 335.1360.

Embodiment 2

[0060] Example 2 1,2-dibenzyl disulfide (LYY-Ι 2 )

[0061] Reference compound LYY-Ι 1 The synthesis method is prepared from benzyl bromide and thiourea to obtain a white solid. Yield 57%. Mp: 64~68℃.

[0062] 1 H NMR (400MHz, CDCl 3 ,δ(ppm):7.35-7.32(m,2H,ArH),7.32-7.28(m,4H,ArH),7.24(dd,J=5.8,4.3Hz,4H,ArH),3.60(s,4H, CH 2 ).

[0063] 13 C-NMR (600MHz, CDCl 3 ), δ(ppm): 137.60, 129.65, 128.72, 127.66, 43.03.

[0064] HR-MS:[M+H] + , Calcd: 247.0615, Found: 247.0611.

Embodiment 3

[0065] Example 3 4,4'-Disulfanediyl bis(methylene)dibenzoate methyl ester (LYY-I 3 )

[0066] Reference compound LYY-Ι 1 The synthesis method is prepared from 4-(bromomethyl)methyl benzoate and thiourea to obtain a white solid. Yield 51%. Mp: 81~85℃.

[0067] 1H NMR (400MHz, CDCl 3 ), δ (ppm): 8.01–7.97 (m, 4H, ArH), 7.28 (d, J = 8.3Hz, 4H, ArH), 3.92 (s, 6H, OCH 3 ),3.62(s,4H,CH 2 ).

[0068] 13C-NMR (600MHz, CDCl 3 ), δ(ppm): 166.80, 142.61, 129.86, 129.41, 129.35, 52.21, 42.91.

[0069] HR-MS:[M+H] + , Calcd: 363.0725, Found: 363.0724.

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Abstract

The invention relates to the technical field of medicines and in particular relates to a diarylmethylene disulfide compound as well as a preparation method and application thereof. An experiment result shows that on a cell model, the diarylmethylene disulfide compound provided by the invention has an effect of inhibiting neurotoxicity caused by excessive glutamic acid and an effect of inhibiting neurotoxicity caused by hydrogen peroxide; the diarylmethylene disulfide compound also has a platelet aggregation resisting effect and can be used for reducing a cerebral infarct area in a mouse MCAO (Middle Cerebral Artery Occlusion) model. The results show that the diarylmethylene disulfide compound provided by the invention can have prevention and / or treatment effects on cerebral stroke.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to diaryl methylene disulfide compounds and their preparation methods and applications. Background technique [0002] "Stroke" (cerebral stroke) is also known as "stroke" and "cerebrovascular accident" (cerebralvascularaccident, CVA). It is an acute cerebrovascular disease, which is a group of diseases that cause brain tissue damage due to sudden rupture of blood vessels in the brain or blockage of blood vessels that prevent blood from flowing into the brain. [0003] Worldwide, stroke is the third leading cause of death and the leading cause of disability in adults. According to statistics, 500,000 to 750,000 people in the United States develop the disease every year. In China, the incidence of cerebral apoplexy reaches 2.5 million / year, and the death toll reaches 1.6 million / year. Stroke has surpassed myocardial infarction and has become the leading cause of death for Chinese...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/12C07C319/24C07C321/20C07C323/56C07C323/07C07D213/65A61K31/497A61K31/105A61K31/235A61K31/24A61K31/444A61P7/02A61P9/10A61P39/06A61P25/00
CPCC07C321/20C07C323/07C07C323/56C07D213/65C07D241/12
Inventor 敖桂珍程坚李玉姚
Owner SUZHOU UNIV
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