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

doi:10.1039/C5OB02586A

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

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8 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 language	English
Pages (from-to)	2134-2144
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	6
DOIs	https://doi.org/10.1039/C5OB02586A
Publication status	Published - 8 Jan 2016

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title = "Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides",

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.",

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

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doi = "10.1039/C5OB02586A",

language = "English",

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T1 - Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides

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.

PY - 2016/1/8

Y1 - 2016/1/8

N2 - 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.

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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DO - 10.1039/C5OB02586A

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EP - 2144

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 6

ER -

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

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Karl Hemming

Farideh Javid

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

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Karl Hemming

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