Synthesis of a Phosphinate Analogue of the Antitumour Phospholipid Edelfosine
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. A synthesis of a phosphinate analogue of the antitumour ether phospholipid edelfosine is described. Both phosphorus–oxygen bonds of the phosphate diester linkage in edelfosine are replaced by phosphorus–carbon bonds, in order to prevent hydrolytic cleavage. Free‐radical addition and Michael‐addition reactions are used to form the two phosphorus–carbon bonds..
| Medienart: |
Artikel |
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| Erscheinungsjahr: |
2015 |
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| Erschienen: |
2015 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:2015 |
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| Enthalten in: |
European journal of organic chemistry - 2015(2015), 22, Seite 4996-5003 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Markoulides, Marios S [VerfasserIn] |
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| Links: |
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| Themen: |
Antitumor agents |
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| RVK: |
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| doi: |
10.1002/ejoc.201500477 |
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OLC1965379516 |
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| 520 | |a 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. A synthesis of a phosphinate analogue of the antitumour ether phospholipid edelfosine is described. Both phosphorus–oxygen bonds of the phosphate diester linkage in edelfosine are replaced by phosphorus–carbon bonds, in order to prevent hydrolytic cleavage. Free‐radical addition and Michael‐addition reactions are used to form the two phosphorus–carbon bonds. | ||
| 540 | |a Nutzungsrecht: Copyright © 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim | ||
| 650 | 4 | |a C‐P bonds | |
| 650 | 4 | |a Radical reactions | |
| 650 | 4 | |a Silyl phosphonites | |
| 650 | 4 | |a Hydrophosphinylation reactions | |
| 650 | 4 | |a Edelfosine | |
| 650 | 4 | |a Phosphinates | |
| 650 | 4 | |a Antitumor agents | |
| 650 | 4 | |a Phospholipids | |
| 700 | 1 | |a Regan, Andrew C |4 oth | |
| 773 | 0 | 8 | |i Enthalten in |t European journal of organic chemistry |d Weinheim : Wiley VCZ, 1998 |g 2015(2015), 22, Seite 4996-5003 |w (DE-627)23976899X |w (DE-600)1410000-9 |w (DE-576)064130681 |x 1434-193X |7 nnns |
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