The synthesis of P-chiral amino acid-derived phosphonamidic anhydrides

Journal of Organic Chemistry

Volumn 65, Issue 15, 2000, Pages 4721-4728

  Sprott, Kevin T ^a   Hanson, Paul R ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; ALENDRONIC ACID; AMINO ACID; PHOSPHONAMIDIC ANHYDRIDE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ANHYDRIDES; BONE RESORPTION; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHONIC ACIDS; PHOSPHORIC ACIDS; STEREOISOMERISM;

EID: 0034725756     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000631b     Document Type: Article

References (64)

1. (a) Tarbell, D. S. Accounts Chem. Res. 1969, 2, 296-300.
2. (b) Soai, K. Yuki Gosei Kagaku Kyokaishi 1987, 45, 1148-56.
3. (c) Martin, A. A.; Barnikow, G. Z. Chem. 1987, 27, 90-95.
4. Eberson, L.; Nyberg, K. Encycl. Electrochem. Elem. 1978, 12, 261-328.
5. (a) Karibian, D.; Jones, C.; Gertler, A.; Dorrington, K. J.; Hofmann, T. Biochemistry 1974, 13, 2891-2897.
6. (b) Hampton, A.; Harper, P. J. Arch. Biochem. Biophys. 1971, 143, 340-341.
7. (c) Yamaguchi, M.; Hatefi, Y. Arch. Biochem. Biophys. 1985, 243, 20-27.
8. (d) Takahashi, K. J. Biochem. 1977, 81, 641-646.
9. (e) Moulin, A.; Fourneron, J.-D.; Piéroni, G.; Verger, R. Biochemistry 1989, 28, 6340-6346.
10. (f) Hampton, A.; Harper, P. J.; Sasaki, T.; Howgate, P.; Preston, R. K. Biochem. Biophys. Res. Commun. 1975, 65, 945-950.
11. (a) Iijima, K.; Katada, J.; Hayashi, Y. Biorg. Med. Chem. Lett. 1999, 9, 413-418.
12. (b) Moorman, A. R.; Abeles, R. H. J. Am. Chem. Soc. 1982, 104, 6785-6786.
13. (c) Baek, D.-J.; Reed, P. E.; Daniels, S. B.; Katzenellenbogen, J. A. Biochemistry 1990, 29, 4305-4311.
14. (d) Gelb, M. H.; Abeles, R. H. J. Med Chem. 1986, 29, 585-589.
15. (e) Ito, K.; Igarashi, K.; Muramatsu, M.; Harada, T.; Hayashi, Y.; Katada, J.; Uno, I. Biochem. Biophys. Res. Commun. 1997, 240, 850-855.
16. (a) Sato, M. Grese, T. A.; Dodge, J. A.; Bryant, H. U.; Turner, C. H. J. Med. Chem. 1999, 42, 1-24.
17. (b) Zimolo, Z.; Wesolowski, G.; Rodan, G. A. J. Clin. Invest. 1995, 96, 2277-2283.
18. (a) Russell, R. G. G. Clin. Endocrinol. 1982, 2, 114-124.
19. (b) Fleisch, H. Bone Miner. Res. 1983, 1, 319-357.
20. (c) Sunberg, R. J.; Ebetino, F. H.; Mosher, C. T.; Roof, C. F. Chemtech 1991, 21, 304-309.
21. (d) Russell, R. G. G.; Rogers, M. J. Bone 1999, 25, 97-106.
22. (e) Shoemaker, L. J. Pedatrics 1999, 134, 264-267.
23. (f) Teronen, O.; Heikkila, P.; Konttinen, Y. T.; Laitinen, M.; Salo, T.; Hanemaaijer, R.; Teronen, A.; Maisi, P.; Sorsa, T. Ann. N. Y. Acad. Sci. 1999, 878, 453-465.
24. a) Fleisch, H. A.; Russell, R. G. G.; Francis, M. D. Science 1969, 165, 1262-1264.
25. (b) Francis, M. D.; Russell, R. G. G.; Fleisch, H. A. Science 1969, 165, 1264-1266.
26. Shinkai, I.; Ohta, Y. Bioorg. Med. Chem. 1996, 4, 3-4.
27. (a) Amin, D.; Cornell, S. A.; Gustafson, S. K.; Needle, S. J.; Ullrich, J. W.; Bilder, G. E.; Perrone, M. H. J. Lipid Res. 1992, 33, 1657-1663.
28. (b) Ciosek, C. P.; Magnin, D. R.; Harrity, T. W.; Logan, J. V. H.; Dickson, J. K.; Gordon, E. M.; Hamilton, K. A.; Jolibois, K. G.; Kunselman, L. K.; Lawrence, R. M.; Mookhtiar, K. A.; Rich, L. C.; Slusarchyk, D. A.; Sulsky, R. B.; Biller, S. A. J. Biol. Chem. 1993, 268, 24832-24837.
29. (c) Magnin, D. R.; Biller, S. A.; Dickson, J. K.; Logan, J. V.; Lawrence, R. M.; Chen, Y.; Sulsky, R. B.; Ciosek, C. P.; Harrity, T. W.; Jolibois, K. G.; Kunselman, L. K.; Rich, L. C.; Slusarchyk, D. A. J. Med. Chem. 1995, 38, 2596-2605.
30. Recently, novel clodronic acid dianhydrides have been shown to be bioreversible prodrugs of clodronate: (a) Ahlmark, M.; Vepsäläinen, J.; Taipale, H.; Niemi, R.; Järvinen, T. J. Med. Chem. 1999, 42, 1473-1476.
31. (b) Hurst, M.; Noble, S. Drugs Aging 1999, 15, 143-167.
32. (c) See also ref 8.
33. Schrader, G. Die Entwicklung neuer insektizider Phosphorsäure-Ester; Verlag Chemie, GmbH.: Germany, 1963.
34. Joesten, M. D.; Chen, Y. T. Inorg. Chem. 1972, 11, 429-431.
35. (a) Healy, J. D.; Shaw, R. A.; Smith, B. C.; Thakur, C. P.; Wood, M. J. Chem. Soc., Dalton Trans. 1974, 12, 1286-1290.
36. (b) Duddeck H.; Lecht, R. Phosphorus Sulfur 1987, 29, 169-178.
37. (c) Breker, J.; Schmutzler, R. Chem. Ber. 1990, 123, 1307-1312.
38. (d) Harger, M. J. P.; Sreedharan-Menon, R. J. Chem. Soc., Perkin Trans. 1 1994, 3261-3267.
39. Hofer, W.; Klaus, L. German Patent, Application: DE 74-2420627 740427.
40. (a) Joesten, M. D. Inorg. Chem. 1967, 6, 1598-1599.
41. (b) Lannert, K. P.; Joesten, M. D. Inorg. Chem. 1968, 7, 2048-2051.
42. (c) Prysak, M. F.; Joesten, M. D. Inorg. Chem. 1969, 8, 1455-1458.
43. (d) Lannert, K. P.; Joesten, M. D. Inorg. Chem. 1969, 8, 1775-1777.
44. (e) Prysak, M. F.; Joesten, M. D. Inorg. Chim. Acta 1970, 4, 383-389.
45. (f) Joesten, M. D.; Smith, H. E.; Vix, V. A. J. Chem. Soc., Chem. Commun. 1973, 18-19.
46. (a) Hanson, P. R.; Stoianova, D. S. Org. Lett. 2000, 2, 1769-1772.
47. (b) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942.
48. (c) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1999, 3297-3300.
49. (d) Hanson, P. R.; Sprott, K. T.; Wrobleski, A. D. Tetrahedron Lett., 1999, 40, 1455-1458.
50. 2- symmetric diastereomers contain a like-relationship between the two stereogenic phosphorus atoms in the optically active compounds 4-15a,b.
51. (a) Dougherty, J. M.; Probst, D. A.; Robinson, R. E.; Moore, J. D.; Klein, T. A.; Snelgrove, K. A.; Hanson, P. R. Tetrahedron 2000, manuscript accepted for publication.
52. (b) Additional results related to the synthesis of seven-membered cyclic sulfamides via RCM strategies are currently the topic of a manuscript submitted for publication.
53. Amino acids have previously been coupled to phosphonic dichlorides, see: (a) Koizumi, T.; Amitani, H.; Yoshii, E. Tetrahedron Lett. 1978, 3741-3742. (b) Koizumi, T.; Kobayashi, Y.; Amitani, H.; Yoshii, E. J. Org. Chem. 1977, 42, 3459-3460.
54. Amino acids have previously been coupled to phosphonic dichlorides, see: (a) Koizumi, T.; Amitani, H.; Yoshii, E. Tetrahedron Lett. 1978, 3741-3742. (b) Koizumi, T.; Kobayashi, Y.; Amitani, H.; Yoshii, E. J. Org. Chem. 1977, 42, 3459-3460.
55. Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677-680.
56. (a) Sprott, K. T.; Hanson, P. R. Abstract of Paper, 219th National Meeting of the American Chemical Society, San Francisco, CA.; Amercan Chemical Society: Washington, DC, 2000; ORGN 825.
57. (b) Additional results related to the synthesis of seven-membered P-heterocycles via RCM strategies are currently the topic of a manuscript submitted for publication.
58. (a) Harger, M. J. P.; Sreedharan-Menon, R. Chem. Commun. 1996, 7, 867-868.
59. (b) Harger, M. J. P.; Sreedharan-Menon, R. J. Chem. Soc., Perkin Trans. 2 1999, 159-164.
60. (c) Harger, M. J. P. Chem. Commun. 1997, 8, 403-404.
61. (d) Harger, M. J. P. J. Chem. Res., Synop. 1996, 110-111.
62. (e) See also ref 12d.
63. Hirschmann, R.; Yager, K. M.; Taylor, C. M.; Witherington, J.; Sprengeler, P. A.; Phillips, B. W.; Moore, W.; Smith, A. B., III. J. Am. Chem. Soc. 1997, 119, 8177-8190.
64. Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.