1. Base catalysed N-functionalisation of boroxazolidones
- Author
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Meenakshisundaram Kandhavelu, J. Mannoja, N. M. Kemppainen, J. Raunio, Nuno R. Candeias, T. Nguyen, Nesar Ahmad, Robert Franzén, Tampere University, Chemistry and Bioengineering, Research group: Industrial Bioengineering and Applied Organic Chemistry, Faculty of Biomedical Sciences and Engineering, and Research group: Molecular Signaling Lab
- Subjects
chemistry.chemical_classification ,Base (chemistry) ,010405 organic chemistry ,General Chemical Engineering ,Aryl ,116 Chemical sciences ,Condensation ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Yield (chemistry) ,Organic chemistry ,Colorectal adenocarcinoma - Abstract
A method for the condensation of boroxazolidones derived from L-valine with aromatic aldehydes, catalysed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene was developed. The preparation and isolation of a series of highly functionalised stable ketimines derived from the reaction of 2,2-diaryl-1,3,2-oxazaborolidin-5-ones with aryl aldehydes is herein described. Several unreported boroxazolidones were prepared by condensation of triethylammonium tetra-arylborates with L-valine in up to 98% yield. The newly synthesised compounds were determined to be moderately cytotoxic against colorectal adenocarcinoma cells, with the best compound in this series having an IC50 of 76 μM. A brief inspection of the effect of the same compound against human brain astrocytoma cells showed an IC50 of 268 μM. publishedVersion
- Published
- 2017