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Synthesis of a Phosphinate Analogue of the Antitumour Phospholipid Edelfosine
Author(s) -
Markoulides Marios S.,
Regan Andrew C.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500477
Subject(s) - phosphinate , chemistry , phospholipid , ether , organic chemistry , silyl ether , membrane , combinatorial chemistry , silylation , biochemistry , catalysis , fire retardant
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.