Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides

J. Blackburn, G. Molyneux, A. Pitard, C. R. Rice, M. I. Page, S. Afshinjavid, F. A. Javid, S. J. Coles, P. N. Horton, K. Hemming

Research output: Contribution to journalArticle

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Abstract

Sixteen new isothiazoloisoxazole 1,1-dioxides, one new isothiazolotriazole and one new isothiazolopyrazole have been synthesised by using 1,3-dipolar cycloadditions to isothiazole 1,1-dioxides. One sub-set of these isothiazoloisoxazoles showed low μM activity against a human breast carcinoma cell line, whilst a second sub-set plus the isothiazolotriazole demonstrated an interesting restricted rotation of sterically hindered bridgehead substituents. A thiazete 1,1-dioxide produced from one of the isothiazole 1,1-dioxides underwent conversion into an unknown 1,2,3-oxathiazolin-2-oxide upon treatment with Lewis acids, but was inert towards 1,3-dipoles and cyclopropenones. Six supporting crystal structures are included.
LanguageEnglish
Pages2134-2144
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number6
DOIs
Publication statusPublished - 8 Jan 2016

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Lewis Acids
Cycloaddition
Cycloaddition Reaction
dioxides
Oxides
Conformations
Thermodynamic properties
Crystal structure
Cells
Breast Neoplasms
Cell Line
synthesis
cycloaddition
cultured cells
breast
cancer
dipoles
acids
crystal structure
oxides

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Blackburn, J. ; Molyneux, G. ; Pitard, A. ; Rice, C. R. ; Page, M. I. ; Afshinjavid, S. ; Javid, F. A. ; Coles, S. J. ; Horton, P. N. ; Hemming, K. / Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides. In: Organic and Biomolecular Chemistry. 2016 ; Vol. 14, No. 6. pp. 2134-2144.
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Blackburn, J, Molyneux, G, Pitard, A, Rice, CR, Page, MI, Afshinjavid, S, Javid, FA, Coles, SJ, Horton, PN & Hemming, K 2016, 'Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides', Organic and Biomolecular Chemistry, vol. 14, no. 6, pp. 2134-2144. https://doi.org/10.1039/C5OB02586A

Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides. / Blackburn, J.; Molyneux, G.; Pitard, A.; Rice, C. R.; Page, M. I.; Afshinjavid, S.; Javid, F. A.; Coles, S. J.; Horton, P. N.; Hemming, K.

In: Organic and Biomolecular Chemistry, Vol. 14, No. 6, 08.01.2016, p. 2134-2144.

Research output: Contribution to journalArticle

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AU - Blackburn, J.

AU - Molyneux, G.

AU - Pitard, A.

AU - Rice, C. R.

AU - Page, M. I.

AU - Afshinjavid, S.

AU - Javid, F. A.

AU - Coles, S. J.

AU - Horton, P. N.

AU - Hemming, K.

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AB - Sixteen new isothiazoloisoxazole 1,1-dioxides, one new isothiazolotriazole and one new isothiazolopyrazole have been synthesised by using 1,3-dipolar cycloadditions to isothiazole 1,1-dioxides. One sub-set of these isothiazoloisoxazoles showed low μM activity against a human breast carcinoma cell line, whilst a second sub-set plus the isothiazolotriazole demonstrated an interesting restricted rotation of sterically hindered bridgehead substituents. A thiazete 1,1-dioxide produced from one of the isothiazole 1,1-dioxides underwent conversion into an unknown 1,2,3-oxathiazolin-2-oxide upon treatment with Lewis acids, but was inert towards 1,3-dipoles and cyclopropenones. Six supporting crystal structures are included.

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