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Preparation and application of 2-(4-substituted phenyl)-3-formamide benzofuranene cyanide compound

A technology of benzofurenyl cyanides and compounds, which is applied in the field of benzofurenyl cyanides and their preparation, and can solve the problems of lack of small molecule drugs, etc.

Active Publication Date: 2019-04-05
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is still a lack of small molecule drugs that use the sortase Sortase A as an inhibitory target in this field

Method used

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  • Preparation and application of 2-(4-substituted phenyl)-3-formamide benzofuranene cyanide compound
  • Preparation and application of 2-(4-substituted phenyl)-3-formamide benzofuranene cyanide compound
  • Preparation and application of 2-(4-substituted phenyl)-3-formamide benzofuranene cyanide compound

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Experimental program
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preparation example Construction

[0073] Preparation of Benzofuryl Cyanides

[0074] The present invention also provides the preparation method of above-mentioned benzofuralene cyanide compound, and its schematic route comprises the steps:

[0075]

[0076] (a) get 1 molar equivalent of 2-hydroxybenzaldehyde and 1 molar equivalent of triphenyl (4-methylbenzyl) phosphine chloride in acetonitrile to reflux for 12 hours to obtain (E)-2-(4-methyl styryl) phenol.

[0077] (b) get 1 molar equivalent of (E)-2-(4-methylstyryl) phenol and 6 molar equivalents of potassium carbonate and 6 molar equivalents of iodine in tetrahydrofuran at room temperature for 1 hour to obtain 2-(4 -methylphenyl)benzofuran.

[0078] (c) Take 1 molar equivalent of 2-(4-methylphenyl)benzofuran, 8 molar equivalents of phosphorus oxychloride and 8 molar equivalents of N.N-dimethylformamide in 1,2-dichloroethane Heated under reflux in alkanes for 12 hours to obtain 2-(4-methylphenyl)benzofuran-3-aldehyde.

[0079] (d) Take 1 molar equiva...

Embodiment 1

[0111] Synthesis of E-2-(4-methylstyryl)phenol (Ⅰ)

[0112] Dissolve compound XII (100g, 248.2mmol) and 2-hydroxybenzaldehyde in 350mL of acetonitrile, stir at room temperature and slowly add DBU (91.3mL, 595.7mmol) dropwise, after the dropwise addition, heat and stir under reflux for 12h to complete the reaction, and cool to Concentrate the reaction solution at room temperature, neutralize with dilute hydrochloric acid to neutrality, add 200mL of water and extract 3 times with ethyl acetate, combine the organic phases, wash with 200mL saturated brine, dry over anhydrous sodium sulfate, concentrate the organic layer, and separate by silica gel chromatography Purified white solid powder I (31.8 g, yield=61%). 1 H NMR (400MHz, DMSO-d 6 )9.67(s,1H),7.52(d,J=7.43Hz,1H),7.40(d,J=7.83Hz,2H),7.32(d,J=16.82Hz,1H),7.09-7.17(m, 3H), 7.01-7.08(m, 1H), 6.83(d, J=7.83Hz, 1H), 6.77(t, J=7.43Hz, 1H), 2.27(s, 3H)

Embodiment 2

[0114] Synthesis of 2-(4-methylphenyl)benzofuran(Ⅱ)

[0115] Compound I (5.4g, 25.7mmol) and anhydrous K 2 CO 3 (21.2g, 154.2mmol) was dissolved in 150mL of tetrahydrofuran, and after stirring at room temperature for 1 hour, elemental iodine powder (39.4g, 154.2 mmol) was added in one go. A saturated aqueous solution of sodium sulfite was used to remove unreacted iodine, extracted three times with ethyl acetate, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated organic layer, separated and purified by silica gel column chromatography to obtain white powder compound II ( 5.03 g, yield=94%). 1 H NMR (400MHz, DMSO-d 6 )7.78(d, J=8.22Hz, 2H), 7.57(d, J=8.61Hz, 1H), 7.60(d, J=7.43Hz, 1H), 7.32(s, 1H), 7.28(d, J= 8.22 Hz, 2H), 7.24 (dd, J = 1.17, 6.26 Hz, 1H), 7.19-7.22 (m, 1H), 2.32 (s, 3H).

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Abstract

The invention provides a preparation and application of a 2-(4-substituted phenyl)-3-formamide benzofuranene cyanide compound. The benzofuranene cyanide compound shown in formula I has a structure shown in the following formula I, wherein the definition of all groups is as described in the description. The compound of the invention adopts Sortase A enzyme as an inhibition target and can be used for preparing drugs for treating and preventing staphylococcus aureus infection. (Shown in the description).

Description

technical field [0001] The present invention relates to a compound in the technical field of medicine and chemical industry and its preparation, in particular to a benzofuralene cyanide compound and its preparation method and application. Background technique [0002] Staphylococcus aureus is a major commensal human pathogen that can cause a wide range of human diseases, causing moderate soft tissue infections and even more severe infections such as endocarditis, pneumonia, septic shock, necrotizing fasciitis, Osteomyelitis and blood infection etc. Staphylococcus aureus has received much attention from the scientific community due to the continuous increase and spread of its multidrug resistant (MDR) strains, such as vancomycin-resistant Staphylococcus aureus (VRSA) and methicillin-resistant Staphylococcus aureus Staphylococcus aureus (MRSA), a condition that leads to increased morbidity and mortality among patients, presents a serious challenge for clinical treatment. [...

Claims

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Application Information

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IPC IPC(8): C07D307/84A61K31/343A61P31/04
CPCA61P31/04C07D307/84Y02A50/30
Inventor 傅磊胡杨姜发琴张勇张东东
Owner SHANGHAI JIAO TONG UNIV
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