Synthesis of a phosphinate analogue of the anti-tumour phosphate di-ester perifosine via sequential radical processes.
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.
School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
Marios S
MS
Markoulides
Andrew C
AC
Regan
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D006868:Hydrolysis; D010720:Phosphines / Q000737:chemistry*; D010721:Phosphinic Acids / Q000737:chemistry*; D010767:Phosphorylcholine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000970:Antineoplastic Agents; D004952:Esters; D005609:Free Radicals; D010720:Phosphines; D010721:Phosphinic Acids; D010767:Phosphorylcholine; C105905:perifosine