Antimicrobial and antimycobacterial activities of aliphatic amines derived from vanillin

Author:

Patterson Alyssa E.1,Flewelling Andrew J.23,Clark Trevor N.23,Geier Stephen J.1,Vogels Christopher M.1,Masuda Jason D.4,Gray Christopher A.23,Westcott Stephen A.1

Affiliation:

1. Department of Chemistry and Biochemistry, Mount Allison University, Sackville, NB E4L 1G8, Canada.

2. Department of Biology, University of New Brunswick, Saint John, NB E2L 4L5, Canada.

3. Department of Chemistry, University of New Brunswick, Fredericton, NB E3B 5A3, Canada.

4. Department of Chemistry, St. Mary’s University, Halifax, NS B3H 3C3, Canada.

Abstract

Ten lipophilic amines were prepared from the reductive amination of vanillin and the corresponding primary amines using sodium borohydride in methanol. All compounds have been obtained elementally pure and an X-ray diffraction study on the 4-n-butylaniline derivative has confirmed the molecular structure. Whilst the overall antibiotic activity of the derivatives was low, some of these compounds, particularly the boronate ester 2-methoxy-4-((2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)phenol (7), showed a promising degree of antimycobacterial activity against Mycobacterium tuberculosis H37Ra, where activity seemed to vary by the position of the boron substitution on the aniline ring.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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