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.

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A small family of organometallic platinum complexes containing a chloride, ciscyclooctene, and a Schiff base ligand have been prepared and characterized fully. Three aliphatic amines and four aromatic amines were chosen as representative examples. All complexes were stable in air except for 7, derived from the pinacol-protected 4-aminophenylboronate ester 4-H2NC6H4Bpin (pin = 1,2-O2C2Me4), which decomposed via B-C bond cleavage.Both complex 4 (derived from aniline) and 7 were further characterized by single crystal X-ray diffraction studies and confirmed the square planar nature of the platinum center whereby the chloride ligand lies trans to the deprotonated hydroxyl group of the Schiff base ligand. The imine functionality is trans to the organic cyclooctene group. Complex 3, which contained the longest aliphatic chain studied (an octyl group), was the most promising for inducing apoptosis in the malignant MB231 breast cancer cell line. Conversely, complexes 4-6, which contained aromatic groups, were the most active against Renal Cell Carcinoma (RCC) cell lines. Graphical Abstract: Seven new organometallic (salicylaldiminato)platinum(II) complexes have been prepared, and characterized fully, whereupon six of these new compounds were examined for their in vitro cytotoxic properties against breast cancer cell line MB231 and Renal Cell Carcinoma (RCC) cell lines.