Synthesis and antimicrobial evaluation of 3-substituted-imine-6-hydroxy-benzofuran derivatives

Wan He; Buzhe Xu; Jian Bao; Xinxian Deng; Wenlu Liu; Yong Zhang; Faqin Jiang; Lei Fu

doi:10.1007/s00044-016-1694-8

Synthesis and antimicrobial evaluation of 3-substituted-imine-6-hydroxy-benzofuran derivatives

Wan He, Buzhe Xu, Jian Bao, Xinxian Deng, Wenlu Liu, Yong Zhang, Faqin Jiang^*, Lei Fu

^*Corresponding author for this work

Shanghai Jiao Tong University

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

A series of 3-substituted-imine-6-hydroxy-benzofuran derivatives were chemically synthesized and biologically evaluated as antibacterial and antifungal agents against Candida albicans, Escherichia coli, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus and Bacillus subtilis. Most compounds showed a selective antibacterial activity to gram-positive bacteria and four compounds revealed great antibacterial activities against methicillin-resistant Staphylococcus aureus comparing to the positive control (Ceftazidime) with MIC₈₀ = 12.5–25 μg/mL. Structure-activity relationship studies demonstrated that the free hydroxy group at the C-6 position is essential to the antibacterial activity, and the aromatic imine fragment at the C-3 position also greatly increases antibacterial activity.

Original language	English
Pages (from-to)	2485-2497
Number of pages	13
Journal	Medicinal Chemistry Research
Volume	25
Issue number	11
DOIs	https://doi.org/10.1007/s00044-016-1694-8
Publication status	Published - 1 Nov 2016
Externally published	Yes

Keywords

Antibacterial activity
Benzofuran derivatives
SAR
Synthesis

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10.1007/s00044-016-1694-8

Cite this

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abstract = "A series of 3-substituted-imine-6-hydroxy-benzofuran derivatives were chemically synthesized and biologically evaluated as antibacterial and antifungal agents against Candida albicans, Escherichia coli, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus and Bacillus subtilis. Most compounds showed a selective antibacterial activity to gram-positive bacteria and four compounds revealed great antibacterial activities against methicillin-resistant Staphylococcus aureus comparing to the positive control (Ceftazidime) with MIC80 = 12.5–25 μg/mL. Structure-activity relationship studies demonstrated that the free hydroxy group at the C-6 position is essential to the antibacterial activity, and the aromatic imine fragment at the C-3 position also greatly increases antibacterial activity.",

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T1 - Synthesis and antimicrobial evaluation of 3-substituted-imine-6-hydroxy-benzofuran derivatives

AU - He, Wan

AU - Xu, Buzhe

AU - Bao, Jian

AU - Deng, Xinxian

AU - Liu, Wenlu

AU - Zhang, Yong

AU - Jiang, Faqin

AU - Fu, Lei

PY - 2016/11/1

Y1 - 2016/11/1

N2 - A series of 3-substituted-imine-6-hydroxy-benzofuran derivatives were chemically synthesized and biologically evaluated as antibacterial and antifungal agents against Candida albicans, Escherichia coli, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus and Bacillus subtilis. Most compounds showed a selective antibacterial activity to gram-positive bacteria and four compounds revealed great antibacterial activities against methicillin-resistant Staphylococcus aureus comparing to the positive control (Ceftazidime) with MIC80 = 12.5–25 μg/mL. Structure-activity relationship studies demonstrated that the free hydroxy group at the C-6 position is essential to the antibacterial activity, and the aromatic imine fragment at the C-3 position also greatly increases antibacterial activity.

AB - A series of 3-substituted-imine-6-hydroxy-benzofuran derivatives were chemically synthesized and biologically evaluated as antibacterial and antifungal agents against Candida albicans, Escherichia coli, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus and Bacillus subtilis. Most compounds showed a selective antibacterial activity to gram-positive bacteria and four compounds revealed great antibacterial activities against methicillin-resistant Staphylococcus aureus comparing to the positive control (Ceftazidime) with MIC80 = 12.5–25 μg/mL. Structure-activity relationship studies demonstrated that the free hydroxy group at the C-6 position is essential to the antibacterial activity, and the aromatic imine fragment at the C-3 position also greatly increases antibacterial activity.

KW - Antibacterial activity

KW - Benzofuran derivatives

KW - SAR

KW - Synthesis

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DO - 10.1007/s00044-016-1694-8

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JO - Medicinal Chemistry Research

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ER -

Synthesis and antimicrobial evaluation of 3-substituted-imine-6-hydroxy-benzofuran derivatives

Abstract

Keywords

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