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

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.
1477-0520
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.
5fd4cd74-6183-48ce-b38d-915f9450e6e1
Afshinjavid, S.
28d6e285-d32a-4f30-95b5-acbe5972204f
Javid, F.A.
0b8cc052-7608-4f1b-93bd-b00650151174
Coles, S.J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, P.N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hemming, K.
d4db0561-9863-4d13-b322-07024a2af087
Blackburn, J.
306255bf-66cf-4794-8d60-bb20b4667032
Molyneux, G.
923940ea-e0bd-4801-821c-a505c660018d
Pitard, A.
d01c262a-3e0e-47b2-b71e-6c6231d50521
Rice, C.R.
15e6c9f8-7dde-44ad-b8b4-8d60040e54da
Page, M.I.
5fd4cd74-6183-48ce-b38d-915f9450e6e1
Afshinjavid, S.
28d6e285-d32a-4f30-95b5-acbe5972204f
Javid, F.A.
0b8cc052-7608-4f1b-93bd-b00650151174
Coles, S.J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, P.N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hemming, K.
d4db0561-9863-4d13-b322-07024a2af087

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), 2134-2144. (doi:10.1039/c5ob02586a).

Record type: Article

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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Accepted/In Press date: 8 January 2016
e-pub ahead of print date: 8 January 2016
Published date: 14 February 2016

Identifiers

Local EPrints ID: 393263
URI: https://eprints.soton.ac.uk/id/eprint/393263
ISSN: 1477-0520
PURE UUID: 908b656c-3b1a-4885-b6f9-b29a5405fcc0
ORCID for S.J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for P.N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

Catalogue record

Date deposited: 25 Apr 2016 11:07
Last modified: 06 Jun 2018 12:54

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