Synthesis and antibacterial activity of four natural chalcones and their derivatives
[Display omitted] •First total syntheses of three natural chalcones were achieved.•The synthesized compounds were investigated for their antibacterial activities.•The 3′-hydroxyisoprenyl group is shown to correlate with antibacterial activities. Four natural chalcones bearing hydroxyisoprenyl or pre...
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Published in | Tetrahedron letters Vol. 60; no. 43; pp. 151165 - 151167 |
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Main Authors | , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
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Elsevier Ltd
24.10.2019
Elsevier |
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Abstract | [Display omitted]
•First total syntheses of three natural chalcones were achieved.•The synthesized compounds were investigated for their antibacterial activities.•The 3′-hydroxyisoprenyl group is shown to correlate with antibacterial activities.
Four natural chalcones bearing hydroxyisoprenyl or prenyl groups, named Paratocarpin E (2), Xanthoangelol D (3), Angusticornin A (4) and Kanzonol C (5), were prepared by employing the Claisen-Schmidt condensation as the key step. In an attempt to investigate the effect of the hydroxyisoprenyl group on biological activity, two of their derivatives were also prepared for antibacterial activity research. The synthesized compounds were investigated for their expected antibacterial activities against Gram positive bacteria (Bacillus subtilis, Staphylococcus aureus) as well as Gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa). Paratocarpin E (2) was found to be the most potent against two Gram positive bacteria while the majority of the remaining compounds showed promising activity as well. However, all of the compounds were inactive against both Gram-negative bacteria. |
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AbstractList | Four natural chalcones bearing hydroxyisoprenyl or prenyl groups, named Paratocarpin E (2), Xanthoangelol D (3), Angusticornin A (4) and Kanzonol C (5), were prepared by employing the Claisen-Schmidt condensation as the key step. In an attempt to investigate the effect of the hydroxyisoprenyl group on biological activity, two of their derivatives were also prepared for antibacterial activity research. The synthesized compounds were investigated for their expected antibacterial activities against Gram positive bacteria (Bacillus subtilis, Staphylococcus aureus) as well as Gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa). Paratocarpin E (2) was found to be the most potent against two Gram positive bacteria while the majority of the remaining compounds showed promising activity as well. However, all of the compounds were inactive against both Gram-negative bacteria. (C) 2019 Elsevier Ltd. All rights reserved. [Display omitted] •First total syntheses of three natural chalcones were achieved.•The synthesized compounds were investigated for their antibacterial activities.•The 3′-hydroxyisoprenyl group is shown to correlate with antibacterial activities. Four natural chalcones bearing hydroxyisoprenyl or prenyl groups, named Paratocarpin E (2), Xanthoangelol D (3), Angusticornin A (4) and Kanzonol C (5), were prepared by employing the Claisen-Schmidt condensation as the key step. In an attempt to investigate the effect of the hydroxyisoprenyl group on biological activity, two of their derivatives were also prepared for antibacterial activity research. The synthesized compounds were investigated for their expected antibacterial activities against Gram positive bacteria (Bacillus subtilis, Staphylococcus aureus) as well as Gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa). Paratocarpin E (2) was found to be the most potent against two Gram positive bacteria while the majority of the remaining compounds showed promising activity as well. However, all of the compounds were inactive against both Gram-negative bacteria. |
ArticleNumber | 151165 |
Author | Chen, Zhiwei Zhang, Jing Li, Yuanyuan Zhang, Shuxin Fu, Lin Xie, Wenhai Liu, Hongliang Deng, Hongkuan Sang, Feng Sun, Bingxia Zhai, Jiadai |
Author_xml | – sequence: 1 givenname: Yuanyuan surname: Li fullname: Li, Yuanyuan organization: School of Life Science, Shandong University of Technology, Zibo 255049, PR China – sequence: 2 givenname: Bingxia surname: Sun fullname: Sun, Bingxia organization: School of Life Science, Shandong University of Technology, Zibo 255049, PR China – sequence: 3 givenname: Jiadai surname: Zhai fullname: Zhai, Jiadai organization: School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, PR China – sequence: 4 givenname: Lin surname: Fu fullname: Fu, Lin organization: School of Life Science, Shandong University of Technology, Zibo 255049, PR China – sequence: 5 givenname: Shuxin surname: Zhang fullname: Zhang, Shuxin organization: School of Life Science, Shandong University of Technology, Zibo 255049, PR China – sequence: 6 givenname: Jing surname: Zhang fullname: Zhang, Jing organization: School of Life Science, Shandong University of Technology, Zibo 255049, PR China – sequence: 7 givenname: Hongliang surname: Liu fullname: Liu, Hongliang organization: School of Life Science, Shandong University of Technology, Zibo 255049, PR China – sequence: 8 givenname: Wenhai surname: Xie fullname: Xie, Wenhai organization: School of Life Science, Shandong University of Technology, Zibo 255049, PR China – sequence: 9 givenname: Hongkuan surname: Deng fullname: Deng, Hongkuan organization: School of Life Science, Shandong University of Technology, Zibo 255049, PR China – sequence: 10 givenname: Zhiwei surname: Chen fullname: Chen, Zhiwei organization: Institute of Food and Nutrition Science, Shandong University of Technology, Zibo 255049, PR China – sequence: 11 givenname: Feng surname: Sang fullname: Sang, Feng email: fengsang@sdut.edu.cn organization: School of Life Science, Shandong University of Technology, Zibo 255049, PR China |
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Keywords | Natural product Antibacterial activity Hydroxyisoprenyl group Chalcone POTENT BIOLOGICAL EVALUATION DORSTENIA-ANGUSTICORNIS FLAVONOIDS TWIGS CONSTITUENTS |
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•First total syntheses of three natural chalcones were achieved.•The synthesized compounds were investigated for their antibacterial... Four natural chalcones bearing hydroxyisoprenyl or prenyl groups, named Paratocarpin E (2), Xanthoangelol D (3), Angusticornin A (4) and Kanzonol C (5), were... |
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SubjectTerms | Antibacterial activity Chalcone Chemistry Chemistry, Organic Hydroxyisoprenyl group Natural product Physical Sciences Science & Technology |
Title | Synthesis and antibacterial activity of four natural chalcones and their derivatives |
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