Andrew Regan

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Organization: The University of Manchester , England
Department: School of Chemistry
Title: Lecture(PhD)

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Co-reporter:Marios S. Markoulides ;Andrew C. Regan
European Journal of Organic Chemistry 2015 Volume 2015( Issue 22) pp:4996-5003
Publication Date(Web):
DOI:10.1002/ejoc.201500477

Abstract

The first concise synthesis of a phosphinate analogue of the antitumour ether phospholipid edelfosine is described. The key synthetic step comprised the free-radical addition reaction of phosphinic acid to a functionalised allyl ether, to incorporate the hydrophobic tail into a monosubstituted H-phosphinic acid. The hydrophilic head group was then added by using a silyl phosphonite based Michael addition. The reported synthetic study lays the groundwork for the synthesis of modified phosphinate phospholipid derivatives to facilitate investigations on their biological activity as membrane-targeting antitumour agents.

Co-reporter:Marios S. Markoulides and Andrew C. Regan  
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 1) pp:119-129
Publication Date(Web):03 Oct 2012
DOI:10.1039/C2OB26395E
An efficient synthesis of a phosphinate analogue of the anti-tumour phosphate di-ester perifosine is described (6 steps and 50% overall yield). The two phosphorus–carbon bonds in the perifosine analogue were prepared by sequential double radical hydrophosphinylation processes. This is the first example of a phosphinate analogue of perifosine, designed to be resistant to hydrolysis by phospholipid-metabolizing enzymes.
Co-reporter:Marios S. Markoulides, Andrew C. Regan
Tetrahedron Letters 2011 Volume 52(Issue 23) pp:2954-2956
Publication Date(Web):8 June 2011
DOI:10.1016/j.tetlet.2011.03.107
Efficient synthesis of phosphinate analogues (in six steps and 68–69% overall yields) of the anti-tumour agent miltefosine are reported, which involve a radical hydrophosphinylation addition reaction followed by conversion to the P(III) silyloxy intermediate and Michael-type addition as the key steps.
Co-reporter:Marios S. Markoulides and Andrew C. Regan
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 1) pp:NaN129-129
Publication Date(Web):2012/10/03
DOI:10.1039/C2OB26395E
An efficient synthesis of a phosphinate analogue of the anti-tumour phosphate di-ester perifosine is described (6 steps and 50% overall yield). The two phosphorus–carbon bonds in the perifosine analogue were prepared by sequential double radical hydrophosphinylation processes. This is the first example of a phosphinate analogue of perifosine, designed to be resistant to hydrolysis by phospholipid-metabolizing enzymes.
Acetaldehyde, (hexadecyloxy)-
Butanoic acid, 3-hydroxy-2-methyl-, ethyl ester, (R*,R*)-
Butanoic acid, 2,3-dimethyl-, methyl ester
2-Furanacetic acid, 5-ethyl-, methyl ester
[2,2'-Bifuran]-5(2H)-one, 4',5'-dihydro-3-methoxy-4-methyl-, (±)-
Butanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-, (R*,R*)-
1,7-Dioxaspiro[5.5]undec-3-ene-2,5-dione, 4-methoxy-3-methyl-, (±)-
Phosphorane, (iodomethylene)triphenyl-
Stannane, tributyl(tetrahydro-2-furanyl)-
BUTANENITRILE, 3-METHYL-2-[(TRIMETHYLSILYL)OXY]-