Base catalysed N-functionalisation of boroxazolidones

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

doi:10.1039/c7ra03266h

Base catalysed N-functionalisation of boroxazolidones

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

^*Corresponding author for this work

Not published at Aalto University

Tampere University

Research output: Contribution to journal › Article › Scientific › peer-review

5 Citations (Scopus)

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 language	English
Pages (from-to)	20620-20627
Number of pages	8
Journal	RSC Advances
Volume	7
Issue number	33
DOIs	https://doi.org/10.1039/c7ra03266h
Publication status	Published - 2017
MoE publication type	A1 Journal article-refereed

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title = "Base catalysed N-functionalisation of boroxazolidones",

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.",

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T1 - Base catalysed N-functionalisation of boroxazolidones

AU - Raunio, J.

AU - Mannoja, J.

AU - Nguyen, T.

AU - Ahmad, N.

AU - Kemppainen, N. M.

AU - Franzén, R. G.

AU - Kandhavelu, M.

AU - Candeias, N. R.

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

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U2 - 10.1039/c7ra03266h

DO - 10.1039/c7ra03266h

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SN - 2046-2069

VL - 7

SP - 20620

EP - 20627

JO - RSC Advances

JF - RSC Advances

IS - 33

ER -

Base catalysed N-functionalisation of boroxazolidones

Abstract

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