Synthesis, biological evaluation and molecular docking analysis of 2-phenyl-benzofuran-3-carboxamide derivatives as potential inhibitors of Staphylococcus aureus Sortase A

He, Wan; Zhang, Yong; Bao, Jiaqi; Deng, Xinxian; Batara, Jennifer; Casey, Shawn Patrick; Guo, Qiuyuan; Jiang, Faqin; Fu, Lei

doi:10.1016/j.bmc.2016.12.030

Cited by 26 publications

(11 citation statements)

References 25 publications

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“…The effort to discover a Sortase A inhibitor has identified various structural scaffolds as potentially clinical useful solutions. These include: 2-phenylbenzofuran-3-carboxamide [ 18 ], 2-phenylbenzo[ d ]oxazole-7-carboxamide [ 19 ], 2-(2-phenylhydrazinylidene)alkanoic acids [ 20 ], benzisothiazolinone [ 21 ], indolethiazolidine [ 22 ], rhodanines [ 23 ], diarylacrylonitriles, triazolo-thiadiazole [ 24 ], and other structures as presented in the reviews of these fields [ 16 , 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

New 2-Phenylthiazoles as Potential Sortase A Inhibitors: Synthesis, Biological Evaluation and Molecular Docking

et al. 2017

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Sortase A inhibition is a well establish strategy for decreasing bacterial virulence by affecting numerous key processes that control biofilm formation, host cell entry, evasion and suppression of the immune response and acquisition of essential nutrients. A meta-analysis of structures known to act as Sortase A inhibitors provided the starting point for identifying a new potential scaffold. Based on this template a series of new potential Sortase A inhibitors, that contain the 2-phenylthiazole moiety, were synthesized. The physicochemical characterisation confirmed the identity of the proposed structures. Antibacterial activity evaluation showed that the new compounds have a reduced activity against bacterial cell viability. However, the compounds prevent biofilm formation at very low concentrations, especially in the case of E. faecalis. Molecular docking studies performed estimate that this is most likely due to the inhibition of Sortase A. The new compounds could be used as add-on therapies together with known antibacterial agents in order to combat multidrug-resistance enterococcal infections.

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Section: Introductionmentioning

confidence: 99%

New 2-Phenylthiazoles as Potential Sortase A Inhibitors: Synthesis, Biological Evaluation and Molecular Docking

et al. 2017

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“…Several significant small organic molecules have been designed and synthesized, as shown in Figure 2 , with promising IC 50 values. Herein, the concrete synthetic features and the analytic properties for structural identification are described in the order of diarylacrylonitriles [ 38 ], pyridazinones [ 39 ], aryl 3-acryloamides [ 40 ], dihydro-β-carboline [ 41 ], benzisothiazolinones [ 42 ], triazolothiadiazoles [ 43 ], 2-(2-phenylhydrazinylidene)alkanoates [ 44 ], 2-phenyl-benzo[ d ]oxazole-7-carboxamide [ 45 ], 2-phenyl-benzofuran-7-carboxamide [ 46 ], 2-phenylthiazoles [ 47 ], 2, 5-disubstitued thiadiazole [ 48 ], and thiadiazolidinedione [ 49 ].…”

Section: Resultsmentioning

confidence: 99%

“…During the search for a new frame of sortase A inhibitors, the Jiang and Fu research group developed L-shaped kinked molecules that mimic the sortase A substrate, LPXTG, sequentially designing 2-phenyl-benzo[d]oxazole-7-carboxamide and 2-phenyl-benzofuran-3-carboxamide [ 45 , 46 ]. Sortase A is known to recognize the LPXTG sorting signal (X means any amino acids) which is arranged in an L-shape mode by the L (Leu) and P (Pro) residues.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Small Molecules as Potent Staphylococcus aureus Sortase A Inhibitors

Paek

2020

Antibiotics

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The widespread and uncontrollable emergence of antibiotic-resistant bacteria, especially methicillin-resistant Staphylococcus aureus, has promoted a wave of efforts to discover a new generation of antibiotics that prevent or treat bacterial infections neither as bactericides nor bacteriostats. Due to its crucial role in virulence and its nonessentiality in bacterial survival, sortase A has been considered as a great target for new antibiotics. Sortase A inhibitors have emerged as promising alternative antivirulence agents against bacteria. Herein, the structural and preparative aspects of some small synthetic organic compounds that block the pathogenic action of sortase A have been described.

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“…For example, (+)-liphagal is a selective phosphoinositide-3-kinase -inhibitor (Marion et al, 2006), cyclopenta [b]benzofuran compounds possess antitumour and antiviral activities (Kim et al, 2006), while derivatives of egonol have antioxidant and anti-inflammatory activities (Timmers et al, 2015). Synthetic benzofuran derivatives are found to possess antitumour and anticancer (Shi et al, 2016;Marquès et al, 2016;Napió rkowska et al, 2019;Asadi et al, 2017), antimicrobial (Asadi et al, 2017;He et al, 2017;Xu et al, 2019) and antitubercular (Xu et al, 2019) activities. Some synthetic benzofuran derivatives have been investigated in the role of osteogenic (Marquè s et al, 2016;Kushwaha et al, 2018;Modukuri et al, 2017) or vasorelaxant (Hassan et al, 2014) agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure and in vitro cytotoxicity testing of some 2-aroylbenzofuran-3-ols

Cong¹,

Trang²,

Dũng³

et al. 2020

Acta Crystallogr C Struct Chem

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Five 2-aroyl-5-bromobenzo[b]furan-3-ol compounds (two of which are new) and four new 2-aroyl-5-iodobenzo[b]furan-3-ol compounds were synthesized starting from salicylic acid. The compounds were characterized by mass spectrometry and 1H NMR and 13C NMR spectroscopy. Single-crystal X-ray diffraction studies of four compounds, namely, (5-bromo-3-hydroxybenzofuran-2-yl)(4-fluorophenyl)methanone, C15H8BrFO3, (5-bromo-3-hydroxybenzofuran-2-yl)(4-chlorophenyl)methanone, C15H8BrClO3, (5-bromo-3-hydroxybenzofuran-2-yl)(4-bromophenyl)methanone, C15H8Br2O3, and (4-bromophenyl)(3-hydroxy-5-iodobenzofuran-2-yl)methanone, C15H8BrIO3, were also carried out. The compounds were tested for their in vitro cytotoxicity on the four human cancer cell lines KB, Hep-G2, Lu-1 and MCF7. Six compounds show good inhibiting abilities on Hep-G2 cells, with IC50 values of 1.39–8.03 µM.

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Synthesis, biological evaluation and molecular docking analysis of 2-phenyl-benzofuran-3-carboxamide derivatives as potential inhibitors of Staphylococcus aureus Sortase A

Cited by 26 publications

References 25 publications

New 2-Phenylthiazoles as Potential Sortase A Inhibitors: Synthesis, Biological Evaluation and Molecular Docking

New 2-Phenylthiazoles as Potential Sortase A Inhibitors: Synthesis, Biological Evaluation and Molecular Docking

Design and Synthesis of Small Molecules as Potent Staphylococcus aureus Sortase A Inhibitors

Synthesis, structure and in vitro cytotoxicity testing of some 2-aroylbenzofuran-3-ols

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