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- Title
Antimicrobial and antimycobacterial activities of aliphatic amines derived from vanillin.
- Authors
Patterson, Alyssa E.; Flewelling, Andrew J.; Clark, Trevor N.; Geier, Stephen J.; Vogels, Christopher M.; Masuda, Jason D.; Gray, Christopher A.; Westcott, Stephen A.
- 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.
- Subjects
ANTI-infective agents; LIPOPHILICITY; ALIPHATIC amine synthesis; SODIUM borohydride; VANILLIN; AMINATION; X-ray diffraction; SUBSTITUTION reactions
- Publication
Canadian Journal of Chemistry, 2015, Vol 93, Issue 11, p1305
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/cjc-2015-0400