Optimisation of the synthesis of second generation 1,2,4,5 tetraoxane antimalarials

Paul M. O' Neill; Sunil Sabbani; Gemma L. Nixon; Matthew Schnaderbeck; Natalie L. Roberts; Emma R. Shore; Christopher Riley; Ben Murphy; Paul McGillan; Stephen A. Ward; Jill Davies; Richard K. Amewu

doi:10.1016/j.tet.2016.08.043

Optimisation of the synthesis of second generation 1,2,4,5 tetraoxane antimalarials

Paul M. O' Neill, Sunil Sabbani, Gemma L. Nixon, Matthew Schnaderbeck, Natalie L. Roberts, Emma R. Shore, Christopher Riley, Ben Murphy, Paul McGillan, Stephen A. Ward, Jill Davies, Richard K. Amewu

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

An efficient route to the synthesis of potent antimalarial aryloxy 1,2,4,5-tetraoxanes is described that permits parallel synthesis for Structure–Activity Relationship (SAR) investigations. Brief details of the in vitro and in vivo antimalarial evaluation are included which enables identification of antimalarial leads for further development. Also described is an improved approach to the synthesis of a selected late-lead compound in just four or five synthetic steps from commercially available starting materials.

Original language	English
Pages (from-to)	6118-6126
Number of pages	9
Journal	Tetrahedron
Volume	72
Issue number	40
DOIs	https://doi.org/10.1016/j.tet.2016.08.043
Publication status	Published - 2016

Keywords

Antimalarial
Chemoselective reduction
Medicinal chemistry
Peroxide chemistry
Reductive amination

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10.1016/j.tet.2016.08.043

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title = "Optimisation of the synthesis of second generation 1,2,4,5 tetraoxane antimalarials",

abstract = "An efficient route to the synthesis of potent antimalarial aryloxy 1,2,4,5-tetraoxanes is described that permits parallel synthesis for Structure–Activity Relationship (SAR) investigations. Brief details of the in vitro and in vivo antimalarial evaluation are included which enables identification of antimalarial leads for further development. Also described is an improved approach to the synthesis of a selected late-lead compound in just four or five synthetic steps from commercially available starting materials.",

keywords = "Antimalarial, Chemoselective reduction, Medicinal chemistry, Peroxide chemistry, Reductive amination",

author = "{O' Neill}, {Paul M.} and Sunil Sabbani and Nixon, {Gemma L.} and Matthew Schnaderbeck and Roberts, {Natalie L.} and Shore, {Emma R.} and Christopher Riley and Ben Murphy and Paul McGillan and Ward, {Stephen A.} and Jill Davies and Amewu, {Richard K.}",

note = "Publisher Copyright: {\textcopyright} 2016",

year = "2016",

doi = "10.1016/j.tet.2016.08.043",

language = "English",

volume = "72",

pages = "6118--6126",

journal = "Tetrahedron",

issn = "0040-4020",

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number = "40",

}

TY - JOUR

T1 - Optimisation of the synthesis of second generation 1,2,4,5 tetraoxane antimalarials

AU - O' Neill, Paul M.

AU - Sabbani, Sunil

AU - Nixon, Gemma L.

AU - Schnaderbeck, Matthew

AU - Roberts, Natalie L.

AU - Shore, Emma R.

AU - Riley, Christopher

AU - Murphy, Ben

AU - McGillan, Paul

AU - Ward, Stephen A.

AU - Davies, Jill

AU - Amewu, Richard K.

PY - 2016

Y1 - 2016

N2 - An efficient route to the synthesis of potent antimalarial aryloxy 1,2,4,5-tetraoxanes is described that permits parallel synthesis for Structure–Activity Relationship (SAR) investigations. Brief details of the in vitro and in vivo antimalarial evaluation are included which enables identification of antimalarial leads for further development. Also described is an improved approach to the synthesis of a selected late-lead compound in just four or five synthetic steps from commercially available starting materials.

AB - An efficient route to the synthesis of potent antimalarial aryloxy 1,2,4,5-tetraoxanes is described that permits parallel synthesis for Structure–Activity Relationship (SAR) investigations. Brief details of the in vitro and in vivo antimalarial evaluation are included which enables identification of antimalarial leads for further development. Also described is an improved approach to the synthesis of a selected late-lead compound in just four or five synthetic steps from commercially available starting materials.

KW - Antimalarial

KW - Chemoselective reduction

KW - Medicinal chemistry

KW - Peroxide chemistry

KW - Reductive amination

UR - http://www.scopus.com/inward/record.url?scp=84986571187&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2016.08.043

DO - 10.1016/j.tet.2016.08.043

M3 - Article

AN - SCOPUS:84986571187

SN - 0040-4020

VL - 72

SP - 6118

EP - 6126

JO - Tetrahedron

JF - Tetrahedron

IS - 40

ER -

Optimisation of the synthesis of second generation 1,2,4,5 tetraoxane antimalarials

Abstract

Keywords

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