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OBSERVATION OF ANTIBIOTIC ACTIVITY OF POTENTIAL 3-ALKOXY-5-ISOXAZOLIDINONES BASED ON RATIONAL CHEMISTRY

BUISSON, NICOLAS PIERRE
http://rave.ohiolink.edu/etdc/view?acc_num=ucin1188440093

Abstract Details

2007, MS, University of Cincinnati, Arts and Sciences : Chemistry.
Ten product mixtures were synthesized following a common synthetic scheme (appendix I) developed through rational chemistry that would lead to the end product being ten different 3-Alkoxy-5-Isoxazolidinones. The ten product mixtures varied only in the structure of the attached carboxylic acid chain. Each reproducibly demonstrated antibiotic activity, but only after the reaction was completed; no precursor materials demonstrated antibiotic activity. Antibiotic activity was demonstrated against a survey of three organisms (Bacillus subtilis, Mycobacterium smegmatis, and Mycobacterium phlei) through bioassay experiments. Additionally, a minimum inhibitory concentration (MIC) experiment on one product mixture also demonstrated antibiotic activity. Two showed the best antibiotic activity against our survey. These were 2-(3-methoxy-4-amino-5-isoxazolidinyl)-3-methylbutyric acid (a branched carboxylic acid chain) and 2-(3-methoxy-4-amino-5-isoxazolidinyl) octanoic acid. Three product mixtures demonstrated the least antibiotic activity. These were 2-(3-methoxy-4-amino-5-isoxazolidinyl) decanoic acid, 2-(3-methoxy-4-amino-5-isoxazolidinyl) lauric acid, and 2-(3-methoxy-4-amino-5-isoxazolidinyl) hexadecanoic acid. The remaining five seemed to demonstrate a connection between lowered antibiotic activity and longer carboxylic acid chains; the two most effective product mixtures were exceptions. Infrared spectroscopy was primarily used to determine carbonyl functionality that may suggest isoxazolidinone functionality. Mass spectroscopic (MS) analysis was performed on some of the compounds, and on one compound H-NMR was performed. This research is strictly qualitative in nature.
Dr. Richard Day (Advisor)
82 p.
3-Alkoxy-5-Isoxazolidinones; 5-Isoxazolidinone; Antibiotic

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Citations

  • BUISSON, N. P. (2007). OBSERVATION OF ANTIBIOTIC ACTIVITY OF POTENTIAL 3-ALKOXY-5-ISOXAZOLIDINONES BASED ON RATIONAL CHEMISTRY [Master's thesis, University of Cincinnati]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1188440093

    APA Style (7th edition)

  • BUISSON, NICOLAS. OBSERVATION OF ANTIBIOTIC ACTIVITY OF POTENTIAL 3-ALKOXY-5-ISOXAZOLIDINONES BASED ON RATIONAL CHEMISTRY. 2007. University of Cincinnati, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ucin1188440093.

    MLA Style (8th edition)

  • BUISSON, NICOLAS. "OBSERVATION OF ANTIBIOTIC ACTIVITY OF POTENTIAL 3-ALKOXY-5-ISOXAZOLIDINONES BASED ON RATIONAL CHEMISTRY." Master's thesis, University of Cincinnati, 2007. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1188440093

    Chicago Manual of Style (17th edition)

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© 2007, all rights reserved.
This open access ETD is published by University of Cincinnati and OhioLINK.