1. Antimicrobial and antimycobacterial activities of aliphatic amines derived from vanillin
- Author
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Patterson, Alyssa E., Flewelling, Andrew J., Clark, Trevor N., Geier, Stephen J., Vogels, Christopher M., Masuda, Jason D., Gray, Christopher A., and Westcott, Stephen A.
- Subjects
X-rays -- Diffraction ,Vanillin -- Physiological aspects -- Research ,Antibiotics -- Chemical properties -- Research ,Chemistry - 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. Key words: aliphatic amines, antimicrobial, antimycobacterial, boronate esters, lipophilic, tuberculosis. Nous avons prepare dix amines lipophiles par amination reductrice de la vanilline avec les amines primaires correspondantes a l'aide du borohydrate de sodium dans le methanol. La purete des composes obtenus a ete verifiee par analyse elementaire, et une etude par diffraction des rayons X du derive 4-n-butylaniline a permis de confirmer la structure moleculaire. Bien que l'activite antibiotique des derives ait ete faible, certains de ces composes, en particulier l'ester boronique 2-methoxy-4-([2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino]methyl)phenol (7), a fait preuve, dans une mesure prometteuse, d'une activite antimycobacterienne contre Mycobacterium tuberculosis H37Ra, ou l'activite semblait varier selon la position du substituant de bore sur le noyau aniline. [Traduit par la Redaction] Mots-cles: amines aliphatiques, agent antimicrobien, agent antimycobacterien, esters boroniques, lipophile, tuberculose., Introduction Although organoboron compounds, particularly boronic acids [RB[(OH).sub.2]] and boronate esters [RB[(OR').sub.2]], are ubiquitous in organic synthesis, (1,2) recent research has also found that these same small molecules can display [...]
- Published
- 2015
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