Heterodimeric bis(amino thiol) complexes of oxorhenium(V) that mimic the structure of steroid hormones. Synthesis and stereochemical issues

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2624-2631

  Hom, Roy K ^a   Chi, Dae Yoon ^a,b   Katzenellenbogen, John A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b Inha University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ANDROGEN; METAL COMPLEX; RHENIUM COMPLEX;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MODEL; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0029922771     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951995k     Document Type: Article

References (38)

1. (a) Muenze, R.; Berger, R. Radiachim. Acta 1987, 41 (2-3), 97.
2. (b) Boyd, R E. Radiochim. Acta 1987, 41 (2-3), 59.
3. Deutsch, E.; Libson, K.; Vanderheyden, J. L. In Technetium and Rhenium in Chemistry and Nuclear Medicine; Nicolmi, M., Bandoli, G., Mazzi. U., Eds.; Raven Press: New York, 1990; pp 14-22.
4. (a) Oya, S.; Kung, M.-P.; Frederick, D.; Kung, H. F. Nucl. Med. Biol. 1995, 22, 749.
5. (b) Charbonnel-Jobic, F.; Guemas, J.-P.; Adelaere, R.; Parrain, J.-L.; Quintard, J.-P. Bull. Soc. Chim. Fr. 1995, 132, 624.
6. (c) Francesconi, L. C.; Yang, Y. Y.; Kung, M.-P.; Zhang, X. X.; Billings, J. J.; Guo, Y.-Z.; Kung, H. F. J. Med. Chem. 1994, 37, 3282.
7. (d) Cros, G.; Belhadj Tahar. H.; de Montauzon, D.; Gleizes, A.; Coulais, Y.; Guiraud, R.; Bellande, E.; Pasqualini, R. Inorg Chim. Acta 1994, 227, 25.
8. (e) Coulais, Y ; Cros, G.; Darbieu, M. H.; Tafani, J. A. M.; Belhadj Tahar. H.; Bellande, E.; Pasqualini, R.; Guiraud, R Nucl. Med. Biol. 1994, 21, 263.
9. (f) Stepniak-Biniakiewicz, D.; Chen, B.; Deutsch, E. J. Med. Chem. 1992. 35, 274.
10. (g) Marzilli, L. G.; Banaszczyk, M. G.; Hansen, L., Kuklenyik, Z.; Cini, R.; Taylor, A., Jr. Inorg. Chem. 1994, 33, 4850.
11. (a) DiZio, J. P.; Fiaschi, R.; Davison, A.; Jones, A. G.; Katzenellenbogen, J. A. Bioconjugate Chem. 1991, 2, 353.
12. (b) DiZio, J. P.; Anderson, C. J.; Davison, A.; Ehrhardt, G. J.; Carlson, K. E.; Welch, M. J.; Katzenellenbogen, J. A. J. Nucl. Med. 1992, 33, 558.
13. (c) O'Neil, J. P.; Carlson, K. E.; Anderson, C. J.; Welch, M. J.; Katzenellenbogen, J. A. Bioconjugate Chem. 1994, 5, 182.
14. (d) Lever, S. Z.; Baidoo, K. E.; Mahmood, A.; Matsumura, K.; Scheffel, U.; Wagner, H. N. Nucl. Med. Biol. 1994, 21, 157.
15. (e) Del Rosario, R. B.; Jung, Y.-W.; Baidoo, K. E., Lever, S. Z.; Wieland, D. M. Nucl Med. Biol. 1994, 21, 197.
16. (a) Chi, D. Y.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1993, 115, 7045.
17. (b) Chi, D. Y.; O'Neil, J. P.; Anderson, C. J.; Welch, M. J.; Katzenellenbogen, J. A. J. Med. Chem. 1994, 37, 928.
18. Hughes, D. L. In Organic Reactions: Paquette, L. A., Ed.-in-Chief; John Wiley & Sons. New York, 1992; Vol. 42, Chapter 2.
19. O'Neil, J. P.; Wilson, S. R.; Katzenellenbogen, J. A. Inorg. Chem. 1994, 33, 319.
20. (a) Lever, S. Z.; Baidoo, K. E.; Mahmood, A. Inorg. Chim. Acta 1990, 176, 183.
21. (b) Mahmood, A.; Halpin, W. A.; Baidoo, K. E.; Sweigart, D. A.; Lever, S. Z. In Technetium and Rhenium in Chemistry and Nuclear Medicine; Nicolini, M. Bandoli, G., Mazzi, U., Eds.; Raven Press New York, 1990; pp 113-118.
22. (a) Schultze, L. M.; Todaro, L. J.; Baldwin, R. M.; Byrne, E. F.; McBride, B. J. Inorg. Chem. 1994, 33, 5579.
23. (b) Chi, D. Y.; Wilson, S. R.; Katzenellenbogen, J. A. Inorg. Chem. 1995, 34, 1624.
24. (c) Rao, T. N.; Adhikesavalu, D.; Camerman, A.; Fritzberg, A. R. J. Am. Chem. Soc. 1990, 112, 5798.
25. (d) Fietz, T.; Spies, H.; Pietzsch, H.-J.; Leibnitz, P. Inorg. Chim. Acta 1995, 231, 233.
26. (e) John, C. S.; Kung, M.-P.; Billings, J.; Kung, H. F. Nucl. Med. Biol. 1991, 18, 551.
27. (f) McDonnell, A. C.; Hambley, T. W.; Snow. M. R.; Wedd, A. G. Aust. J. Chem. 1983, 36, 253.
28. (g) Bandoli, G.; Gerber, T. I. A. Inorg. Chim. Acta 1987, 126, 205.
29. Ochiai, E. Aromatic Amine Oxides; Elsevier: New York, 1967; pp 290-302.
30. (a) Tamaru, Y.; Kawamura, S.; Bando, T., Tanaka, K.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5491.
31. (b) Tamaru, Y.; Kawamura, S.; Tanaka, K.; Yoshida, Z. Tetrahedron Lett. 1984, 25, 1063.
32. Mitsunobu, O. Synthesis 1981, 1.
33. Dodge, J. A.; Trujillo, J. I.; Presnell, M. J. Org. Chem. 1994, 59, 234.
34. Cotton. F. A.; Lippard, S. J. Inorg. Chem. 1966, 5, 9.
35. Minick, D. J.; Frenz, J. H.; Patrick, M. A.; Brent, D. A. J. Med. Chem. 1988, 31, 1923.
36. Brandes, S. J ; Katzenellenbogen, J. A. Mol. Pharmacol. 1987, 32, 391.
37. Mohmadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R. Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J Comput. Chem. 1990, 11, 440.
38. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923