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

4 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)2134-2144
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number6
DOIs
Publication statusPublished - 8 Jan 2016

    Fingerprint

Cite this