The University of Southampton
University of Southampton Institutional Repository

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.
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.
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.

Text
KH_2015_002586_final_amended_untracked.pdf - Accepted Manuscript
Download (960kB)

More information

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: http://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: 15 Mar 2024 03:04

Export record

Altmetrics

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: S.J. Coles ORCID iD
Author: P.N. Horton ORCID iD
Author: K. Hemming

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×