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

doi:10.1039/c7ra03266h

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

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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
Publication type	A1 Journal article-refereed

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Base catalysed N-functionalisation of boroxazolidones
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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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year = "2017",

doi = "10.1039/c7ra03266h",

language = "English",

volume = "7",

pages = "20620--20627",

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T1 - Base catalysed N-functionalisation of boroxazolidones

AU - J., Raunio

AU - Mannoja, J.

AU - Nguyen, T.

AU - N., Ahmad

AU - N. M., Kemppainen

AU - Franzén, R. G.

AU - Kandhavelu, M.

AU - Candeias, N. R.

N1 - INT=keb,"Raunio, J." INT=tut-bmt,"Nguyen, T." INT=tut-bmt,"Ahmad, N." INT=keb,"Kemppainen, N. M."

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.

U2 - 10.1039/c7ra03266h

DO - 10.1039/c7ra03266h

M3 - Article

SN - 2046-2069

VL - 7

SP - 20620

EP - 20627

JO - RSC Advances

JF - RSC Advances

IS - 33

ER -

Base catalysed N-functionalisation of boroxazolidones

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