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Benzofuran compound, preparation method and applications thereof

A technology of benzofuran and compound, applied in the field of benzofuran compound and its preparation, 2, can solve the problem of bacterial drug resistance and so on

Inactive Publication Date: 2016-02-17
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional antibacterial drugs mostly aim at killing bacteria, which is also the main factor leading to bacterial resistance

Method used

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  • Benzofuran compound, preparation method and applications thereof
  • Benzofuran compound, preparation method and applications thereof
  • Benzofuran compound, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Synthesis of Triphenyl-(4-Methylbenzyl)phosphine Chloride

[0049] 4-Methylbenzyl chloride (50g, 356mmol) and triphenylphosphine (93.3g, 356mmol) were dissolved in 200mL of acetonitrile, heated to reflux for 6 hours, a white solid was formed, cooled to room temperature, filtered, and the residue was washed with 30mL After washing with ether three times, the residue was collected and vacuum-dried to obtain a white powder of triphenyl-(4-methylbenzyl)phosphine chloride (102 g, yield: 70%). 1HNMR (400MHz, DMSO-d 6 ), 8.00(d, J=7.04Hz, 1H), 7.89-7.97(m, J=8.22Hz, 2H), 7.65(d, J=7.83Hz, 1H), 7.41-7.49(m, J=8.22Hz , 2H), 7.36 (quin, J=6.85Hz, 2H), 4.56 (s, 2H).

Embodiment 2

[0051] Synthesis of E-2-(4-methylstyryl)phenol

[0052] Dissolve triphenyl-(4-methylbenzyl)phosphine chloride (100g, 248.2mmol) and 2-hydroxybenzaldehyde in 350mL acetonitrile, stir at room temperature and slowly add DBU (91.3mL, 595.7mmol), dropwise After the addition is complete, heat and stir under reflux for 12 hours to complete the reaction, cool to room temperature, concentrate the reaction solution, neutralize with dilute hydrochloric acid to neutrality, add 200 mL of water and extract 3 times with ethyl acetate, combine the organic phases, wash with 200 mL of saturated brine, anhydrous Dry over sodium sulfate, concentrate the organic layer, and separate and purify the white solid powder E-2-(4-methylstyryl)phenol (31.8 g, yield=61%) through silica gel column chromatography. 1 HNMR (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(...

Embodiment 3

[0054] Synthesis of 2-(4-methylphenyl)benzofuran

[0055] E-2-(4-methylstyryl)phenol 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, 154.2mmol) was added in one go. The unreacted iodine was removed by a saturated aqueous solution of sodium sulfite, extracted three times with ethyl acetate, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, the organic layer was concentrated, separated and purified by silica gel chromatography to obtain a white powder compound 2- (4-Methylphenyl)benzofuran (5.03 g, yield=94%). 1H NMR (400MHz, DMSO-d6) 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=8.22Hz, 2H), 7.24 (dd, J=1.17, 6.26Hz, 1H), 7.19-7.22 (m, 1H), 2.32 (s, 3H).

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Abstract

The present invention provides a benzofuran compound, a preparation method and applications thereof, wherein the structure is represented by a general formula (I-1) or (I-2), R1, R3 and R4 are any one selected from hydrogen, C1-C5 straight or branched chain alkyl, hydroxyl, an aldehyde group, an acetyl group, a carboxyl group, a cyano group, an amino group, a nitro group, fluorine, chlorine, bromine, an amide group, an ester group, an alkoxy group, an aromatic group, and a heteroaromatic group, R2 is any one selected from hydrogen, C1-C5 straight or branched chain alkyl group, a hydroxyl group, an aromatic group, and a heteroaromatic group, and m and n are integers of 0-5. According to the present invention, the Staphylococcus aureus protease Sortase A substrate polypeptide fragment -LPXTG- is adopted as the structural simulation object, the benzofuran structure is adopted as the simulation substrate proline, and the linked amide hydrophobic fragment segment is used to stimulate the substrate leucine residue to design the novel protease Sortase A inhibitor.

Description

technical field [0001] The invention relates to a benzofuran compound and a preparation method thereof, in particular to a 2,3-disubstituted benzofuran compound, a preparation method and application thereof. It belongs to the technical field of medicine and chemical industry. Background technique [0002] In recent years, the serious abuse of antibiotics in my country has become increasingly serious. The resulting antibiotic multidrug-resistant bacteria are developing faster and faster. Especially methicillin-resistant staphylococcus aureus (methicilin-resistantstaphylococcusaureus, MRSA), has become the main pathogenic bacteria causing nosocomial cross-infection since it was discovered and spread globally only ten years ago. There is resistance to most of the current antibiotics, even vancomycin, which is considered to be the most effective against Staphylococcus aureus. In order to cope with the continuous mutation and evolution of bacteria, people have to actively sear...

Claims

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Application Information

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IPC IPC(8): C07D307/84A61P31/04
CPCC07D307/84
Inventor 傅磊姜发琴何宛张勇邓欣贤郭秋圆
Owner SHANGHAI JIAO TONG UNIV
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