Synthesis of phosphinate analogues of the phospholipid anti-tumour agent hexadecylphosphocholine (miltefosine)

Tetrahedron Letters

Volumn 52, Issue 23, 2011, Pages 2954-2956

  Markoulides, Marios S ^a   Regan, Andrew C ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Anti tumour agents; Carbon phosphorus bonds; Miltefosine; Phosphinic acids; Phospholipid analogues; Radical hydrophosphinylation reaction; Silyl phosphonites

Indexed keywords

ANTINEOPLASTIC AGENT; MILTEFOSINE; PHOSPHINATE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYLATION; ARBUZOV REACTION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION;

EID: 79955650620     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.107     Document Type: Article

References (21)

1. F. Mollinedo Expert Opin. Ther. Pat. 17 2007 385 405
2. S.R. Vink, W.J. van Blitterswijk, J.H.M. Schellens, and M. Verheij Cancer Treat. Rev. 33 2007 191 202
3. H. Eibl, and C. Unger Cancer Treat. Rev. 17 1990 233 242
4. C. Oberle, U. Massing, and H.F. Krug Biol. Chem. 386 2005 237 245
5. V. Jendrossek, and R. Handrick Curr. Med. Chem. Anticancer Agents 3 2003 343 353
6. R. Ulbrich-Hofmann, A. Lerchner, M. Oblozinsky, and L. Bezakova Biotechnol. Lett. 27 2005 535 544
7. L.D. Quin A Guide to Organophosphorus Chemistry 2000 John Wiley & Sons New York pp 351-386
8. M. Collinsova, and J. Jiracek Curr. Med. Chem. 7 2000 629 647
9. E.E. Nifant'ev, and M.P. Koroteev J. Gen. Chem. USSR (Engl. Trans.) 37 1967 1293 1297
10. E.E. Nifant'ev, R.K. Magdeeva, and N.P. Shchepet'eva J. Gen. Chem. USSR (Engl. Trans.) 50 1980 1416 1423
11. A.K. Bhatacharya, and G. Thyagarman Chem. Rev. 81 1981 415 430
12. A.N. Pudovik, and B.A. Arbuzov J. Gen. Chem. USSR (Engl. Trans.) 21 1951 423 428
13. E.A. Boyd, K. James, and A.C. Regan Tetrahedron Lett. 33 1992 813 816
14. E.A. Boyd, K. James, and A.C. Regan Tetrahedron Lett. 35 1994 4223 4226
15. S. Deprle, and J. -L. Montchamp J. Org. Chem. 66 2001 6745 6755
16. E.E. Nifant'ev, and L.P. Levitan Zh. Obshch. Khim. 35 1965 758 (Chem. Abstr. 1965, 63, 23689)
17. S.J. Fitch J. Am. Chem. Soc. 86 1964 61 64
18. W.L. Santos, B.H. Heasley, R. Jarosz, K.M. Carter, K.R. Lynch, and T.L. Macdonald Bioorg. Med. Chem. Lett. 14 2004 3473 3476
19. L.C.F. Pimentel, A.L.F. de Souza, T.L. Fernández, J.L. Wardell, and O.A.C. Antunes Tetrahedron Lett. 48 2007 831 833
20. P.S. Watson, B. Jiang, K. Harrison, N. Asakawa, P.K. Welch, M. Covington, N.C. Stowell, E.A. Wadman, P. Davies, K.A. Solomon, R.C. Newton, G.L. Trainor, S.M. Friedman, C.P. Decicco, and S.S. Ko Bioorg. Med. Chem. Lett. 16 2006 5695 5699
21. V. Devreux, J. Wiesner, H. Jomaa, J. van der Eycken, and S. van Calenbergh Bioorg. Med. Chem. Lett. 17 2007 4920 4923