Base catalysed N-functionalisation of boroxazolidones

Raunio J., J. Mannoja, T. Nguyen, Ahmad N., Kemppainen N. M., R. G. Franzén, M. Kandhavelu, N. R. Candeias

    Research output: Contribution to journalArticleScientificpeer-review

    2 Citations (Scopus)
    41 Downloads (Pure)

    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.
    Original languageEnglish
    Pages (from-to)20620-20627
    Number of pages8
    JournalRSC Advances
    Volume7
    Issue number33
    DOIs
    Publication statusPublished - 2017
    Publication typeA1 Journal article-refereed

    Publication forum classification

    • Publication forum level 1

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