Synthesis and in vitro antimicrobial activity of benzo[b][1,4]thiazin-3(4H)-ones via smiles rearrangement
Abstract New benzo[b][1,4]thiazin-3(4H)-one derivatives (compounds 12a–p) were synthesized via Smiles rearrangement and assayed in vitro for their antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. The antimicrobial activity of the benzo[b][1,4]thiazin-3(4H)-ones showed, on the whole, potent toward all tested Gram-positive and Gram-negative microorganism (minimal inhibitory concentration ranging from 16 to 64 μg/ml), whereas weak effectiveness was exhibited against fungi. Data obtained suggested that 12g, 12i, and 12o exerted the best antibacterial activity against Gram-positive bacteria and compound 12b demonstrated the best inhibition of Gram-negative bacteria. These observations provide some predictions to design further antimicrobial active compounds prior to their synthesis following with molecular modeling studies..
Medienart: |
Artikel |
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Erscheinungsjahr: |
2009 |
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Erschienen: |
2009 |
Enthalten in: |
Zur Gesamtaufnahme - volume:20 |
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Enthalten in: |
Medicinal chemistry research - 20(2009), 1 vom: 29. Dez., Seite 93-100 |
Sprache: |
Englisch |
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Beteiligte Personen: |
Yang, Hao [VerfasserIn] |
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Links: |
Volltext [lizenzpflichtig] |
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Themen: |
)-one |
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Anmerkungen: |
© Springer Science+Business Media, LLC 2010 |
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doi: |
10.1007/s00044-009-9288-3 |
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funding: |
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Förderinstitution / Projekttitel: |
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PPN (Katalog-ID): |
OLC2049350627 |
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520 | |a Abstract New benzo[b][1,4]thiazin-3(4H)-one derivatives (compounds 12a–p) were synthesized via Smiles rearrangement and assayed in vitro for their antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. The antimicrobial activity of the benzo[b][1,4]thiazin-3(4H)-ones showed, on the whole, potent toward all tested Gram-positive and Gram-negative microorganism (minimal inhibitory concentration ranging from 16 to 64 μg/ml), whereas weak effectiveness was exhibited against fungi. Data obtained suggested that 12g, 12i, and 12o exerted the best antibacterial activity against Gram-positive bacteria and compound 12b demonstrated the best inhibition of Gram-negative bacteria. These observations provide some predictions to design further antimicrobial active compounds prior to their synthesis following with molecular modeling studies. | ||
650 | 4 | |a Antimicrobial activity | |
650 | 4 | |a Benzo[ | |
650 | 4 | |a ][1,4]thiazin-3(4 | |
650 | 4 | |a )-one | |
650 | 4 | |a Smiles rearrangement | |
650 | 4 | |a Synthesis | |
700 | 1 | |a Fang, Liang |4 aut | |
700 | 1 | |a Li, Zhu-Bo |4 aut | |
700 | 1 | |a Ren, Fang-Kui |4 aut | |
700 | 1 | |a Wang, Li-Ying |4 aut | |
700 | 1 | |a Tian, Xiao |4 aut | |
700 | 1 | |a Shin, Dong-Soo |4 aut | |
700 | 1 | |a Zuo, Hua |4 aut | |
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