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Synthesis of benzo[b][1,4]oxazin-3(4H)-ones via smiles rearrangement for antimicrobial activity

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Abstract

The benzo[b][1,4]oxazin-3(4H)-one derivatives, 1a–p, carrying F, Br, and Cl on the benzene ring, or benzyl, cyclohexyl, n-hexyl, and tetrafuryl methylene groups attached to nitrogen atom 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]oxazin-3(4H)-ones showed, on the whole, potency toward all the tested Gram-positive and Gram-negative microorganism (MIC ranging from 16 to 64 μg/ml), whereas weak effectiveness was exhibited against fungi. Data obtained suggest that fluorine atom in the compounds, 1c, 1f, 1i plays an important role in enhancing the antimicrobial properties of this class of compounds. These observations provide some predictions to design further antimicrobial active compounds prior to their synthesis according to molecular modeling studies.

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Acknowledgements

The authors acknowledge the financial support of the grants from Natural Science Foundation Project of CQ CSTC, 2009BB5007 and National Research Foundation of Korea Grant funded by the Korean Government (2009-0073064).

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Authors and Affiliations

  1. Department of Oncology, The Ninth People’s Hospital of Chongqing, Chongqing, 400700, China

    Liang Fang

  2. College of Pharmaceutical Sciences, Southwest University, Chongqing, 400715, China

    Hua Zuo, Zhu-Bo Li, Xiao-Yan He, Li-Ying Wang & Xiao Tian

  3. Institutes of Organic Chemistry and Developmental Biology, Shandong University, Jinan, 250100, China

    Bao-Xiang Zhao & Jun-Ying Miao

  4. Department of Chemistry, Changwon National University, Changwon, GN, 641-733, South Korea

    Dong-Soo Shin

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  1. Liang Fang
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  2. Hua Zuo
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  3. Zhu-Bo Li
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  4. Xiao-Yan He
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  5. Li-Ying Wang
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Correspondence to Hua Zuo or Dong-Soo Shin.

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Fang, L., Zuo, H., Li, ZB. et al. Synthesis of benzo[b][1,4]oxazin-3(4H)-ones via smiles rearrangement for antimicrobial activity. Med Chem Res 20, 670–677 (2011). https://doi.org/10.1007/s00044-010-9360-z

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  • DOI: https://doi.org/10.1007/s00044-010-9360-z

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