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Kinetic studies of conjugate addition of amines to allenic and acrylic esters and their correlation with antibacterial activities against Staphylococcus aureus

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Abstract

Kinetic reactivities of various allenic and acrylic esters in conjugate addition reactions with various amines were investigated. Competition experiments showed that amines reacted selectively with allenic esters, which was also confirmed by quantitative determination of the rate constants. The antibacterial activity against Staphylococcus aureus of allenic and acrylic ester derivatives were also determined. Allenic esters were found to exhibit a higher antibacterial activity than its acrylic counterparts. A correlation between the kinetic property and the antibacterial activity suggested that a conjugate addition may involve in the antibacterial mechanism of these unsaturated esters.

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Acknowledgements

This research was supported by Thailand Research Fund (Grant MRG5980118), the Faculty of Science, Mahidol University, the National Research Universities Initiative, and the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Ministry of Education (OHEC). C. K. thanks the Sri Trang Thong Scholarship and the Young Scientist Scholarship program, and A. K. thanks the Young Scientist Scholarship program for financial support. We also thank the Department of Chemistry and the Central Instrumental Facility (CIF) at the Faculty of Science, Mahidol University for research facilities.

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Authors and Affiliations

  1. Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, 272 Rama VI Road, Ratchathewi, Bangkok, 10400, Thailand

    Cholpisit Kiattisewee, Angkit Kaidad, Chutima Jiarpinitnun & Torsak Luanphaisarnnont

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  1. Cholpisit Kiattisewee
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  2. Angkit Kaidad
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  3. Chutima Jiarpinitnun
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  4. Torsak Luanphaisarnnont
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Correspondence to Torsak Luanphaisarnnont.

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Kiattisewee, C., Kaidad, A., Jiarpinitnun, C. et al. Kinetic studies of conjugate addition of amines to allenic and acrylic esters and their correlation with antibacterial activities against Staphylococcus aureus. Monatsh Chem 149, 1059–1068 (2018). https://doi.org/10.1007/s00706-018-2175-1

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  • DOI: https://doi.org/10.1007/s00706-018-2175-1

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