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Novel gas signal molecule donator and preparation method and use thereof

A compound and selected technology, applied in the field of medicine, can solve problems such as fatal cardiovascular events, achieve good safety and tolerance, and high pharmacological activity

Inactive Publication Date: 2014-04-23
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Fortunately, after a lot of experiments, the inventor introduced hydrogen sulfide releasing groups into the structure of some compounds, and synthesized a series of compounds with brand new structures. The experimental results show that these compounds may have significant anti-inflammatory and anti-inflammatory properties. / or anti-tumor effect, or no obvious gastrointestinal damage, or both; in addition, new selective non-steroidal anti-inflammatory drugs such as celecoxib have less gastrointestinal damage , but fatal cardiovascular events

Method used

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  • Novel gas signal molecule donator and preparation method and use thereof
  • Novel gas signal molecule donator and preparation method and use thereof
  • Novel gas signal molecule donator and preparation method and use thereof

Examples

Experimental program
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Effect test

Embodiment 2

[0059] Example 2: E-2-(4-methoxyphenyl)-3-(4-methanesulfonylphenyl)-acrylic acid 4-(3H-1,2-dithio-hole-3- Synthesis of Thione-5-yl)-Phenyl Ester (YLXYⅡ-1)

[0060] Will 6a (0.203g, 0.61mmol), ADT-OH (0.152g, 0.67mmol) and BOP (0.323g, 0.73mmol) were added to 15mL of dry THF, then triethylamine (0.35mL, 2.44mmol) was added, stirred at room temperature 12h, then add 15mL ethyl acetate to dilute, then use 1 mol.L -1 Hydrochloric acid solution (3×15mL), saturated NaHCO 3 solution (3×15mL) and saturated brine (3×15mL), and the organic phase was washed with anhydrous MgSO 4 Drying, evaporation to dryness, column chromatography [petroleum ether (60-90):ethyl acetate=6:1 (v / v)], a red solid was obtained with a yield of 85.6%, mp: 72.1~73.1°C.

[0061] 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 8.08 (s, 1H, =CH), 8.00(m, 3H, ArH), 7.83 (m, 3H, ArH), 7.42 (m, 3H, ArH & =CH), 7.28 (d , 2H, J = 8.7 Hz, ArH), 7.00 (d, 2H, J = 7.8 Hz, ArH), 3.77 (s, 3H, CH 3 ), 3.22 (s, 3H, CH 3 ).

...

Embodiment 3

[0065] Example 3: E-2-(2,4-dichlorophenyl)-3-(4-methylsulfonylphenyl)-acrylic acid 4-(3H-1,2-dithio-hole-3 Synthesis of -thione-5-yl)-phenyl ester (YLXYⅡ-2)

[0066] According to the synthetic method of YLXYⅡ-1, ADT-OH and 6b Preparation, red solid, yield 86.9%, mp: 179.1~180.1℃.

[0067] 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 8.28 (s, 1H, =CH), 8.00 (d, 2H, J = 7.7 Hz, ArH), 7.90(m, 4H, ArH), 7.51 (d, 1H, J = 7.1 Hz, ArH), 7.40 (m, 4H, ArH), 6.87(s, 2H, ArH), 6.65(s, 1H, =CH), 3.22 (s, 3H, CH 3 ).

[0068] IR(KBr, cm -1 ): 1739.8 (C=O), 1490.9, 1521.8, 1637.6, 1595.1 (C=C), 1151.5 (C=S).

[0069] HR-MS: Calcd. For C 25 h 16 Cl 2 o 4 S 4 577.9309, Found: 577.9308.

Embodiment 4

[0070] Example 4: E-2-(2-chlorophenyl)-3-(4-methylsulfonylphenyl)-acrylic acid 4-(3H-1,2-dithio-hole-3-thione -5-yl)-phenyl ester (YLXYⅡ- 3 )Synthesis

[0071] According to the synthetic method of YLXYⅡ-1, ADT-OH and 6c Preparation, red solid, yield 81.5%, mp: 176.4-177.4°C.

[0072] 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 8.25 (s, 1H, =CH), 8.01 (d, 2H, J = 8.7 Hz, ArH), 7.83 (m, 3H, ArH & =CH), 7.67 (d, 1H, J = 8.1 Hz, ArH), 7.50 (m, 1H, ArH), 7.42(m, 4H, ArH), 7.37 (d, 2H, J = 2.0 Hz, ArH), 3.22 (s, 3H, CH 3 ).

[0073] 13 C NMR (400MHz, CDCl 3 ), δ(ppm): 220.887, 177.937, 169.575, 158.848, 147.066, 146.892, 143.851, 141.339, 138.985, 138.507, 136.970, 136.844, 136.227, 136.141, 135.213, 134.522, 134.258, 133.484, 132.519, 128.340, 48.500.

[0074]IR(KBr, cm -1 ): 1734.0 (C=O), 1654.9, 1635.6, 1598.9, 1489.0 (C=C), 1151.5 (C=S).

[0075] HR-MS: Calcd. For C 25 h 17 ClO 4 S 4 545.9669, Found: 545.9661.

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Abstract

The invention discloses a novel gas signal molecule donator and a preparation method and medical use thereof, in particular to a compound with new structure and the preparation method and medical use of the compound. The compound is a compound with a general formula YLXYII or the salt of the compound, comprises the portion related with hydrogen sulfide and is often combined with compounds in covalence mode or forms the salt. Pharmacological results show that the compound has remarkable anti-inflammatory effect and tumor resistance without remarkable damage to gastrointestinal tract, so that the compound can be used for preparing and treating various diseases such as inflammation, cardiovascular diseases, and diseases related with tumor. In addition, the preparation method for preparing the compound is further provided.

Description

technical field [0001] The present invention relates to the field of medicine, in particular to several hydrogen sulfide donor compounds and pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions containing these compounds and their medical uses, especially in the preparation of anti-inflammatory, anti- Applications in tumor and anti-cardiovascular disease drugs. Background technique [0002] There are complex and diverse signaling pathways in organisms and cells. Among them, gas signal molecules have attracted widespread attention in the scientific community due to their unique characteristics such as continuous production, rapid transmission, and rapid diffusion. The discovery of gas signal molecules has enabled biomedical research. Entered a new page. The first two gas signal molecules discovered were nitric oxide (NO) and carbon monoxide (CO). The former has been found to have a wide range of biological effects such as dilati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D339/02A61K31/385A61P29/00A61P9/10A61P9/12A61P9/04A61P9/00A61P19/02A61P19/08A61P37/02A61P11/06A61P11/08A61P17/06A61P17/02A61P17/00A61P1/00A61P1/06A61P1/04A61P25/06A61P3/10A61P21/04A61P1/02A61P13/12A61P37/08A61P11/00A61P1/16A61P25/28A61P25/16A61P25/00
Inventor 绪广林盛晶晶郑文杰潘黎黎敖桂珍成静邱婷史方超
Owner NANJING NORMAL UNIVERSITY
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