Synthesis and Antitubercular Activities in Vitro of New p-Aminosalicylic Ester Imines
Michael J. Hearn, Daniel J. Smaltz and Michael H. Cynamon
Affiliation: Department of Chemistry, Wellesley College, Wellesley, Massachusetts 02481.
Keywords: Antimycobacterial properties, Drug design, Inhibitory concentrations, Iron acquisition, Mycobacterium tuberculosis. Para-
In the present study, novel imines (5-16) of para-aminosalicylic esters were prepared in good yield and purity
for the investigation of their antimycobacterial properties in vitro. The chemical structures of the compounds were determined
by IR, 1H-NMR, 13C-NMR, high resolution mass spectrometry and elemental analysis. Unlike para-aminosalicylic
acid itself, these compounds are thermally stable and displayed activity in two models using pathogenic strains of Mycobacterium
tuberculosis. Compound 5, bearing an ortho-hydroxybenzylidene unit, demonstrated promising activity in vitro
and a range of cytotoxic and inhibitory properties that warrant further studies.
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