Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides
Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides
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 ?M 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.
2134-2144
Blackburn, J.
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Molyneux, G.
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Pitard, A.
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Rice, C.R.
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Page, M.I.
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Afshinjavid, S.
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Javid, F.A.
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Coles, S.J.
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Horton, P.N.
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Hemming, K.
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14 February 2016
Blackburn, J.
306255bf-66cf-4794-8d60-bb20b4667032
Molyneux, G.
923940ea-e0bd-4801-821c-a505c660018d
Pitard, A.
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Rice, C.R.
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Page, M.I.
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Afshinjavid, S.
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Javid, F.A.
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Coles, S.J.
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Horton, P.N.
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Hemming, K.
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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. and Hemming, K.
(2016)
Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides.
Organic & Biomolecular Chemistry, 14 (6), .
(doi:10.1039/c5ob02586a).
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 ?M 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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KH_2015_002586_final_amended_untracked.pdf
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Accepted/In Press date: 8 January 2016
e-pub ahead of print date: 8 January 2016
Published date: 14 February 2016
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Local EPrints ID: 393263
URI: http://eprints.soton.ac.uk/id/eprint/393263
ISSN: 1477-0520
PURE UUID: 908b656c-3b1a-4885-b6f9-b29a5405fcc0
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Date deposited: 25 Apr 2016 11:07
Last modified: 15 Mar 2024 03:04
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Contributors
Author:
J. Blackburn
Author:
G. Molyneux
Author:
A. Pitard
Author:
C.R. Rice
Author:
M.I. Page
Author:
S. Afshinjavid
Author:
F.A. Javid
Author:
P.N. Horton
Author:
K. Hemming
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