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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. [ABSTRACT FROM AUTHOR]

Twelve copper(II) Schiff base complexes derived from lipophilic amines have been prepared using either salicylaldehyde or ortho-vanillin via a microwave-assisted reaction. All complexes have been obtained elementally pure and an X-ray diffraction of an isopentyl derivative has confirmed the structure of these compounds. All complexes showed a promising degree of anti-mycobacterial activity against Mycobacterium tuberculosis, where activity seemed to increase with an increase in the length of the aliphatic chain. [ABSTRACT FROM AUTHOR]