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3H-1,2-dithio-cyclopentene-3-thioketone compound and application thereof

A technology of dithiocyclopentene and dithiolane, applied to 3H-1,2-dithiocyclopentene-3-thione compounds, and its application in the preparation of drugs for the treatment or prevention of cerebral apoplexy In this field, it can solve the problem of less therapeutic drugs and achieve the effect of inhibiting the inflammatory response and reducing the volume

Active Publication Date: 2012-12-05
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In short, compared with the high incidence and severity of stroke, there are few current therapeutic drugs

Method used

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  • 3H-1,2-dithio-cyclopentene-3-thioketone compound and application thereof
  • 3H-1,2-dithio-cyclopentene-3-thioketone compound and application thereof
  • 3H-1,2-dithio-cyclopentene-3-thioketone compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Synthesis of 5-p-hydroxyphenyl-3H-1,2-dithiole-3-thione compound (YC1-1)

[0035] Add methyl p-hydroxybenzoyl acetate (307mg, 1.89mmol), phosphorus pentasulfide (420mg, 1.9mmol), sulfur (56mg, 0.93mmol) into 20mL of toluene, heat and reflux for 5h, the reaction is complete, filter, and the filtrate is concentrated Developed by column chromatography (petroleum ether: acetone = 10:1), 134 mg of red solid was obtained with a yield of 40%. m.p.191.3~192.1℃. 1 H NMR (400MHz, DMSO-d 6 ), 10.46(s,1H,OH),7.78(d,2H,J=8.7Hz,ArH),7.68(s,1H,=CH),6.90(d,2H,J=8.7Hz,ArH).HR-MS :Calcd.For C 9 h 6 OS 3 [M+H] + :226.9654,Found:226.9645.

Embodiment 2

[0036] Example 2: Synthesis of 5-p-fluorophenyl-3H-1,2-dithiole-3-thione (YC1-2)

[0037] Using methyl p-fluorobenzoylacetate, phosphorus pentasulfide and sulfur as raw materials, the synthetic method can be found in the synthesis of YC1-1, and the yield is 34%. m.p.108.3~110.0℃. 1 HNMR (400Hz, CDCl 3 ),δ(ppm):7.66(s,2H,ArH),7.37(s,1H,=CH),7.18(s,2H,ArH). 13 C-NMR (400MHz, CDCl 3 ), δ(ppm): 215.398, 171.482, 166.623, 163.247, 135.893, 129.124, 129.007, 117.060, 116.765.HR-MS: Calcd.For C 9 h 5 FS 3 [M+H] + :228.9610,Found:228.9610.

Embodiment 3

[0038] Example 3: Synthesis of 5-(2-thienyl)-3H-1,2-dithiole-3-thione (YC1-3)

[0039] Using methyl 2-thiopheneformylacetate, phosphorus pentasulfide and sulfur as raw materials, the synthesis method can be found in the synthesis of YC1-1, and the yield is 36%. m.p.119.2~120.9℃. 1 HNMR (400Hz, CDCl 3 ),δ(ppm):7.59(s,1H,=CH),7.54(s,1H,ArH),7.32(s,1H,ArH),7.15(s,1H,ArH). 13 C-NMR (400MHz, CDCl 3 ), δ(ppm): 214.456, 165.134, 134.629, 133.866, 131.083, 129.247, 129.065.HR-MS: Calcd.ForC 7 h 7 S 4 [M+H] + :216.9269,Found:216.9268.

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Abstract

The invention relates to the field of medicaments, and in particular relates to a 3H-1,2-dithio-cyclopentene-3-thioketone compound and an application thereof. The 3H-1,2-dithio-cyclopentene-3-thioketone compound disclosed by the invention has a structure shown in a formula I or a formula II and is a compound with a completely-new structure. Proved by experiments, the 3H-1,2-dithio-cyclopentene-3-thioketone compound has a direct protection role on neurons on a cell model, and can obviously restrain excessive inflammatory responses of inflammatory cells in the cerebrum; and by using 3H-1,2-dithio-cyclopentene-3-thioketone, focal cerebral ischemia cerebral infarction volume of a mouse can be obviously reduced in an animal model. Therefore, the invention provides the 3H-1,2-dithio-cyclopentene-3-thioketone compound and the application of acceptable slat of the 3H-1,2-dithio-cyclopentene-3-thioketone compound on the pharmacy aspect to the preparation of medicaments for preventing or treating a cerebral apoplexy disease.

Description

technical field [0001] The invention belongs to the field of medicines, in particular to 3H-1,2-dithiocyclopentene-3-thione compounds and applications thereof, especially to 3H-1,2-dithiocyclopentene-3-thione compounds Application of the compound in the preparation of medicines for treating or preventing cerebral apoplexy. Background technique [0002] Stroke is the third leading cause of death worldwide and the leading cause of disability in adults. According to statistics, in the United States, 500,000 to 750,000 people suffer from stroke every year; in China, the number of stroke cases 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 among Chinese people (Liu L, et al., Stroke. 2011; 42:3651-3654). Stroke not only has a high fatality rate, but up to 75% of stroke patients will also leave sequelae such as neurobehavioral function impairment and cognitive impairment,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04C07D409/04A61K31/385A61K31/4365A61P9/10A61P7/02
CPCC07D409/04C07D409/12C07D339/04A61P7/02A61P9/10
Inventor 程坚敖桂珍贾佳
Owner SUZHOU UNIV
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