Synthesis and Biological Activities of Arylspiroborates Derived from 2,3-Dihydroxynaphthalene
Michael J. Geier
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8 Canada
Search for more papers by this authorEric G. Bowes
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8 Canada
Search for more papers by this authorGraham M. Lee
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8 Canada
Search for more papers by this authorHaoxin Li
Department of Biology, University of New Brunswick, Saint John, New Brunswick, E2L 4L5 Canada
Search for more papers by this authorTaryn O'Neill
Department of Biology, University of New Brunswick, Saint John, New Brunswick, E2L 4L5 Canada
Search for more papers by this authorAndrew Flewelling
Department of Biology, University of New Brunswick, Saint John, New Brunswick, E2L 4L5 Canada
Search for more papers by this authorChristopher M. Vogels
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8 Canada
Search for more papers by this authorAndreas Decken
Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 Canada
Search for more papers by this authorCorresponding Author
Christopher A. Gray
Department of Biology, University of New Brunswick, Saint John, New Brunswick, E2L 4L5 Canada
Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 Canada
Correspondence to: Stephen A. Westcott; e-mail: [email protected]. Christopher A. Gray; e-mail: [email protected].Search for more papers by this authorCorresponding Author
Stephen A. Westcott
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8 Canada
Correspondence to: Stephen A. Westcott; e-mail: [email protected]. Christopher A. Gray; e-mail: [email protected].Search for more papers by this authorMichael J. Geier
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8 Canada
Search for more papers by this authorEric G. Bowes
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8 Canada
Search for more papers by this authorGraham M. Lee
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8 Canada
Search for more papers by this authorHaoxin Li
Department of Biology, University of New Brunswick, Saint John, New Brunswick, E2L 4L5 Canada
Search for more papers by this authorTaryn O'Neill
Department of Biology, University of New Brunswick, Saint John, New Brunswick, E2L 4L5 Canada
Search for more papers by this authorAndrew Flewelling
Department of Biology, University of New Brunswick, Saint John, New Brunswick, E2L 4L5 Canada
Search for more papers by this authorChristopher M. Vogels
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8 Canada
Search for more papers by this authorAndreas Decken
Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 Canada
Search for more papers by this authorCorresponding Author
Christopher A. Gray
Department of Biology, University of New Brunswick, Saint John, New Brunswick, E2L 4L5 Canada
Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 Canada
Correspondence to: Stephen A. Westcott; e-mail: [email protected]. Christopher A. Gray; e-mail: [email protected].Search for more papers by this authorCorresponding Author
Stephen A. Westcott
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8 Canada
Correspondence to: Stephen A. Westcott; e-mail: [email protected]. Christopher A. Gray; e-mail: [email protected].Search for more papers by this authorContract grant sponsor: American Chemical Society—Petroleum Research Foundation.
Contract grant number: 50093-UR3.
Contract grant sponsor: Mount Allison University.
Contract grant sponsor: University of New Brunswick.
Contract grant sponsor: Natural Sciences and Engineering Research Council of Canada (to SAW and CAG).
Contract grant sponsor: Canada Research Chair Program (to SAW).
Contract grant sponsor: New Brunswick Innovation Foundation (to CAG).
Contract grant sponsor: New Brunswick Health Research Foundation (to CAG).
Contract grant sponsor: Harrison McCain Foundation (to CAG).
ABSTRACT
A family of arylspiroborate compounds has been prepared from 2,3-dihydroxynaphthalene and characterized fully using multinuclear NMR spectroscopy and elemental analyses. Single crystal X-ray diffraction studies were carried out on the tetramethylammonium (4) and calcium (6) derivatives. Compound 6 represents the first structurally characterized example of a calcium arylspiroborate salt. All compounds showed modest antifungal and antimycobacterial activities. These results have revealed a new class of compounds that should be further developed to design more potent and selective antitubercular agents. © 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:116–123, 2013; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21072
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