Synthesis and Antimicrobial Activity of Amines and Imines with a Cycloheptatriene Fragment

2013 
N-Benzylidene-4-(1-cyclohepta-2,4,6-trienyl)aniline (IIIa), N-(4-bromophenylmethylene)-41-(1-cyclohepta-2,4,6-trienyl)aniline (IIIb), and N-(4-methoxyphenylmethylene)-41-(1-cyclohepta-2,4,6-trienyl)aniline (IIIc) were prepared by tropylation of the corresponding imines. 4-(5-Dibenzo[a,d]cyclohepten-5-yl)aniline (V) was prepared by the reaction of aniline with dibenzosuberenole (VI); N-benzylidene-4-(5-dibenzo[a,d]cyclohepten-5-yl)aniline (IV), from benzalaniline and V. A study of the antimycobacterial activity of the synthesized compounds showed that IIIa, IIIc, and IV exhibited inhibiting activity against Staphylococcus aureus at concentrations >1000 μg/mL. Compounds IIIa and V at concentrations of 1000 μg/mL inhibited growth of E. coli and Candida albicans, respectively.
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