Synthetic studies toward the preparation of phosphonate analogs of sphingomyelin and ceramide 1-phosphate using pentacovalent organophospholene methodology

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2437-2441

  McClure, Cynthia K ^a   Mishra, Pranab K ^a   Grote, Christopher W ^a,b  

^a MONTANA STATE UNIVERSITY   (United States)

^b EASTMAN KODAK COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CERAMIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SPHINGOMYELIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030916933     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962144v     Document Type: Article

References (35)

1. (a) Cevc, G., Ed. Phospholipids Handbook; Marcel Dekker: New York, 1993.
2. (b) Spence, M. W. In Phosphatidylcholine Metabolism; Vance, D. E., Ed.; CRC Press: Boca Raton, FL, 1989; pp 185-203.
3. (c) Barenholz, Y.; Thompson, T. E. Biochim. Biophys. Acta 1980, 604, 129.
4. (d) Merrill, A. H., Jr.; Jones, D. D. Biochim. Biophys. Acta 1990, 1044, 1.
5. (e) Kolesnick, R. N. Prog. Lipid Res. 1991, 30, 1.
6. (f) Andrieu, N.; Salvayre, R.; Levade, T. Eur. J. Biochem. 1996, 236, 738, and references cited therein,
7. (g) Kishimoto, Y. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1983; Vol. 16, pp 357-407.
8. (h) Rye, K.-A.; Hime, N. J.; Barter, P. J. J. Biol. Chem. 1996, 271, 4243.
9. (i) Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins and Membranes; Vance, D. E., Vance, J., Eds.; Elsevier Science Publishers: New York, 1991; pp 327-361.
10. Brady, R. O. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York; 1983; Vol. 16, pp 409-426.
11. Hannun, Y. A. J. Biol. Chem. 1994, 269, 3125, and references cited therein.
12. (a) Gill, D. L.; Ghosh, T. K.; Bian, J. Science 1990, 248, 1653, and references cited therein,
13. (b) Hannun, Y. A.; Loomis, C. R.; Merrill, A. H., Jr.; Bell, R. M. J. Biol. Chem. 1986, 261, 12604.
14. (c) Hannun, Y. A.; Bell, R. M. Science 1989, 243, 500.
15. Kaczmarek, L. K. Trends Neurosci. 1987, 10, 31.
16. For recent examples, see: (a) Hilderbrand, R. L. The Role of Phosphonates in Living Systems; CRC Press: Boca Raton, FL, 1983. (b) Biryukov, A. I.; Bunik, V. I.; Zhukov, Y. N.; Khurs, E. N.; Khomutov, R. M. FEBS Lett. 1996, 382, 167. (c) Camp, N. P.; Perrey, D. A.; Kinchington, D.; Hawkins, P. C. D.; Gani, D. Bioorg. Med. Chem. 1995, 3, 297. (d) Mannesse, M. L.; Boots, J. W.; Dijkman, R.; Slotboom, A. J.; van der Hijden, H. T.; Egmond, M. R.; Verheij, H. M.; de Haaz, G. H. Biochim. Biophys. Acta 1995, 1259, 56. (e) Chung, S.-K.; Moon, S.-H. Carbohydr. Res. 1994, 260, 39. (f) Schmitt, J. D.; Nixon, A. B.; Emilsson, A.; Daniel, L. W.; Wykle, R. L. Chem. Phys. Lipids 1992, 62, 263.
17. For recent examples, see: (a) Hilderbrand, R. L. The Role of Phosphonates in Living Systems; CRC Press: Boca Raton, FL, 1983. (b) Biryukov, A. I.; Bunik, V. I.; Zhukov, Y. N.; Khurs, E. N.; Khomutov, R. M. FEBS Lett. 1996, 382, 167. (c) Camp, N. P.; Perrey, D. A.; Kinchington, D.; Hawkins, P. C. D.; Gani, D. Bioorg. Med. Chem. 1995, 3, 297. (d) Mannesse, M. L.; Boots, J. W.; Dijkman, R.; Slotboom, A. J.; van der Hijden, H. T.; Egmond, M. R.; Verheij, H. M.; de Haaz, G. H. Biochim. Biophys. Acta 1995, 1259, 56. (e) Chung, S.-K.; Moon, S.-H. Carbohydr. Res. 1994, 260, 39. (f) Schmitt, J. D.; Nixon, A. B.; Emilsson, A.; Daniel, L. W.; Wykle, R. L. Chem. Phys. Lipids 1992, 62, 263.
18. For recent examples, see: (a) Hilderbrand, R. L. The Role of Phosphonates in Living Systems; CRC Press: Boca Raton, FL, 1983. (b) Biryukov, A. I.; Bunik, V. I.; Zhukov, Y. N.; Khurs, E. N.; Khomutov, R. M. FEBS Lett. 1996, 382, 167. (c) Camp, N. P.; Perrey, D. A.; Kinchington, D.; Hawkins, P. C. D.; Gani, D. Bioorg. Med. Chem. 1995, 3, 297. (d) Mannesse, M. L.; Boots, J. W.; Dijkman, R.; Slotboom, A. J.; van der Hijden, H. T.; Egmond, M. R.; Verheij, H. M.; de Haaz, G. H. Biochim. Biophys. Acta 1995, 1259, 56. (e) Chung, S.-K.; Moon, S.-H. Carbohydr. Res. 1994, 260, 39. (f) Schmitt, J. D.; Nixon, A. B.; Emilsson, A.; Daniel, L. W.; Wykle, R. L. Chem. Phys. Lipids 1992, 62, 263.
19. For recent examples, see: (a) Hilderbrand, R. L. The Role of Phosphonates in Living Systems; CRC Press: Boca Raton, FL, 1983. (b) Biryukov, A. I.; Bunik, V. I.; Zhukov, Y. N.; Khurs, E. N.; Khomutov, R. M. FEBS Lett. 1996, 382, 167. (c) Camp, N. P.; Perrey, D. A.; Kinchington, D.; Hawkins, P. C. D.; Gani, D. Bioorg. Med. Chem. 1995, 3, 297. (d) Mannesse, M. L.; Boots, J. W.; Dijkman, R.; Slotboom, A. J.; van der Hijden, H. T.; Egmond, M. R.; Verheij, H. M.; de Haaz, G. H. Biochim. Biophys. Acta 1995, 1259, 56. (e) Chung, S.-K.; Moon, S.-H. Carbohydr. Res. 1994, 260, 39. (f) Schmitt, J. D.; Nixon, A. B.; Emilsson, A.; Daniel, L. W.; Wykle, R. L. Chem. Phys. Lipids 1992, 62, 263.
20. For recent examples, see: (a) Hilderbrand, R. L. The Role of Phosphonates in Living Systems; CRC Press: Boca Raton, FL, 1983. (b) Biryukov, A. I.; Bunik, V. I.; Zhukov, Y. N.; Khurs, E. N.; Khomutov, R. M. FEBS Lett. 1996, 382, 167. (c) Camp, N. P.; Perrey, D. A.; Kinchington, D.; Hawkins, P. C. D.; Gani, D. Bioorg. Med. Chem. 1995, 3, 297. (d) Mannesse, M. L.; Boots, J. W.; Dijkman, R.; Slotboom, A. J.; van der Hijden, H. T.; Egmond, M. R.; Verheij, H. M.; de Haaz, G. H. Biochim. Biophys. Acta 1995, 1259, 56. (e) Chung, S.-K.; Moon, S.-H. Carbohydr. Res. 1994, 260, 39. (f) Schmitt, J. D.; Nixon, A. B.; Emilsson, A.; Daniel, L. W.; Wykle, R. L. Chem. Phys. Lipids 1992, 62, 263.
21. For recent examples, see: (a) Hilderbrand, R. L. The Role of Phosphonates in Living Systems; CRC Press: Boca Raton, FL, 1983. (b) Biryukov, A. I.; Bunik, V. I.; Zhukov, Y. N.; Khurs, E. N.; Khomutov, R. M. FEBS Lett. 1996, 382, 167. (c) Camp, N. P.; Perrey, D. A.; Kinchington, D.; Hawkins, P. C. D.; Gani, D. Bioorg. Med. Chem. 1995, 3, 297. (d) Mannesse, M. L.; Boots, J. W.; Dijkman, R.; Slotboom, A. J.; van der Hijden, H. T.; Egmond, M. R.; Verheij, H. M.; de Haaz, G. H. Biochim. Biophys. Acta 1995, 1259, 56. (e) Chung, S.-K.; Moon, S.-H. Carbohydr. Res. 1994, 260, 39. (f) Schmitt, J. D.; Nixon, A. B.; Emilsson, A.; Daniel, L. W.; Wykle, R. L. Chem. Phys. Lipids 1992, 62, 263.
22. (a) McClure, C. K.; Jung, K.-Y. J. Org. Chem. 1991, 56, 867.
23. (b) McClure, C. K.; Grote, C. W. Tetrahedron Lett. 1991, 32, 5313.
24. (c) McClure, C. K.; Grote, C. W. Tetrahedron Lett. 1993 34, 983.
25. (d) McClure, C. K.; Jung, K.-Y.; Grote, C. W.; Hansen, K. B. Phosphorus Sulfur Silicon 1993, 75, 23.
26. Grote, C. W., Ph.D. thesis, University of Delaware, 1992.
27. (a) Gennari, C.; Colombo, L.; Bertolini, G. J. Am. Chem. Soc. 1986, 108, 6394.
28. (b) Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395.
29. (c) Trimble, L. A.; Vederas, J. C. J. Am. Chem. Soc, 1986, 108, 6397.
30. (d) Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266.
31. Walker, B. J. In Organophosphorus Reagents in Organic Synthesis; Cadogen, J. I. G., Ed.; Academic Press: New York, 1979; pp 155-205.
32. LeBlanc, Y.; Fitzsimmons, B. J., Tetrahedron Lett. 1989, 30, 2889.
33. (a) Kobayashi, S.; Isobe, T.; Ohno, M. Tetrahedron Lett. 1984, 25, 5079.
34. (b) Kano, S.; Yokomatsu, T.; Shibuya, S. Tetrahedron Lett. 1991, 32, 233.
35. (c) Futagawa, S.; Inui, T.; Shiba, T. Bull. Chem. Soc. Jpn. 1973, 46, 3308.