A new approach to phosphonate analogues of phosphatidyl derivatives

European Journal of Organic Chemistry

Volumn , Issue 1, 2003, Pages 224-229

  Brel, Valery K ^a   Stang, Peter J ^b  

^a INSTITUTE OF PHYSIOLOGICALLY ACTIVE COMPOUNDS   (Russian Federation)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

Alkenes; Allenes; Medicinal chemistry; Phospholipids

Indexed keywords

ALKENE DERIVATIVE; ALLENE DERIVATIVE; CARBON; DIACYLGLYCEROL; HYDROGEN; PHOSPHATIDYL DERIVATIVE; PHOSPHOLIPID; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0037241121     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200301)2003:1<224::AID-EJOC224>3.0.CO;2-3     Document Type: Article

References (39)

1. [1a] L. He, H.-S. Byun, R. Bittman, J. Org. Chem. 1998, 63, 5696-5699.
2. [1b] P. R. Cullis, M. J. Hope, B. de Kruijff, A. J. Verkleij, C. P. S. Tilcock, in Phospholipids and Cellular Regulation (Ed.: J. F. Kuo), RC Press, Boca Raton, FL, 1985.
3. [2a] K. Racke, R. Hammermann, U. R. Juergens, Pulm. Pharmacol Ther. 2000, 13, 99-114.
4. [2b] K. R. Lynch, D. W. Hopper, S. J. Carlisle, J. G. Catalano, M. Zhang, T. L. MacDonald, MoL Pharmacol. 1997, 52, 75-81.
5. K. Bandoh, J. Aoki, H. Hosono, S. Kobayashi, T. Kobayashi, K. Murakami-Murofushi, M. Tsujimoto, H. Arai, K. Inoue, J. Biol. Chem. 1999, 274, 27776- 27785.
6. [4a] E. Modest, L. W. Daniel, R. L. Wykle, M. E. Berens, C. Piantadosi, J. R. Surles, S. Morris-Natschke, in New Avenues in Developmental Cancer Chemotherapy, Bristol-Myers Cancer Symposia, Academic Press, New York, 1987; Vol. 8, Ch. 9.
7. [4b] W. E. Berdel, R. Andreesen, P. G. Munder, in Phospholipids and Cellular Regulation (Ed.: J. F. Kuo), CRC Press, Boca Raton, FL, 1985; Vol. II.
8. [4c] G. Arthur, R. Bittman, Biochim. Biophys. Acta 1998, 1390, 85-102.
9. [5a] D. B. J. Herrmann, H. A. Neumann, Lipids 1987, 22, 955-957.
10. [5b] A. Ashagbley, P. Samander, R. Bittman, R. K. Erukulla, H. S. Byun, G. Arthur, Anticancer Res. 1996, 16, 1813-1818.
11. [5c] T. Wieder, W. Reutter, C. E. Orfanos, Ch. C. Geilen, Prog Lipid Res. 1999, 38, 249-259 and references cited therein.
12. [6a] J. A. Harding, C. M. Engbers, M. S. Newman, N. I. Goldstein, S. Zalipsky, Biochim. Biophys. Acta 1997, 1327, 181-192.
13. [6b] D. Kirpotin, J. W. Park, K. Hong, S. Zalipsky, W.-L. Li, P. Carter, C. C. Benz, D. Papahadjopoulos, Biochemistry 1997, 36, 66-75.
14. C.-C. Kan, R. Bittman, J. Hajdu, Biochim. Biophys. Acta 1991, 1066, 95-101 and references cited therein.
15. [8a] S. F. Martin, Y.-L. Wong, A. S. Wagman, J. Org. Chem. 1994, 63, 4821-4831.
16. [8b] B. N. Thomas, R. C. Corcoran, C. L. Cotant, C. M. Lindemann, J. E. Kirsch, P. J. Persixhini, J. Am. Chem. Soc. 1998, 120, 12178-12186.
17. [8c] K. L. Meyer, C. J. Marasco, Jr., S. L. Morris-Natschke, K. S. Ishaq, C. Piantadosi, J. Med. Chem. 1991, 34, 1377-1383.
18. J. Chen, G. D. Prestwich, J. Org. Chem. 1998, 63, 430-438.
19. [10a] R. Bittman, H.-S. Byun, B. Mercier, H. Salari, J. Med. Chem. 1993, 36, 297-299.
20. [10b] Z. Li, S. Racha, E. Abushanab, Tetrahedron Lett. 1993, 34, 3539-3542.
21. [10c] R. D. Chambers, R. Jaouhari, D. O'Hagan, J. Chem. Soc., Chem. Commun. 1988, 69-70.
22. [10d] T. K. Vinod, O. H. Griffith, J. F. W. Keana, Tetrahedron Lett. 1994, 35, 7193-7196.
23. [11a] R. Engel, Chem. Rev. 1977, 77, 349-367.
24. [11b] R. Engel, in The Role of Phosphonates in Living Systems (Ed.: R. L. Hidetband), CRC Press, Inc., Boca Raton, FL, 1988.
25. [12a] V. K. Brel, Synth. Commun. 2002, 32, 2855-2862.
26. [12b] V. K. Brel, Synthesis 2001, 1539-1545.
27. [12c] V. K. Brel, Synth. Commun. 1999, 29, 3869-3880.
28. [12d] V. K. Brel, Synthesis 1998, 710-712.
29. [12e] V. K. Brel, P. J. Stang, 224th ACS National Meeting, 2002, Abstract 134, Boston, Division of Organic Chemistry.
30. Ch. R. Schmid, J. D. Bryant, M. Dowlatzedah, J. L. Phillips, D. E. Prather, R. D. Schantz, N. L. Sear, C. S. Vianco, J. Org. Chem. 1991, 56, 4056-4064.
31. G. J. F. Chittenden, Carbohydr. Res. 1980, 84, 350-357.
32. Y.-L. Zhong, T. K. M. Shing, J. Org. Chem. 1997, 62, 2622-2624.
33. L. Brandsma, Preparative Acetylenie Chemistry, Elsevier, Amsterdam, 1988.
34. [17a] V. Mark, Tetrahedron Lett. 1962, 281-285.
35. [17b] V. Mark, in Mechanism of Molecular Migrations (Ed.: B. S. Thyagajaran), Wiley, New York, 1969, vol. 3.
36. R. Wolfgang, in The Chemistry of Allenes (Ed.: S. R. Landor), Academic Press, London, 1982, vol. 2.
37. H. B. Lazrek, A. Rochdi, H. Khaider, J.-L. Barascut, J.-L. Imbach, J. Balzarini, M. Witvrouw, C. Pannecouque, E. de Clercq, Tetrahedron 1998, 54, 3807-3816.
38. [20a] C. E. McKenna, J. Schmidhauser, J. Chem. Soc., Chem. Commun. 1979, 739-741.
39. [20b] C. L. Salomon, E. Breuer, Tetrahedron Lett. 1995, 36, 6759-6762.