Control of the platinum(II) ligating properties of rigid 1,2-diamines: the case of trans-2,3-diaminonorbornane

Tetrahedron Letters

Volumn 47, Issue 46, 2006, Pages 8091-8093

  Maisonial, Aurélie ^a   Traikia, Mounir ^a   Gautier, Arnaud ^a   Aitken, David J ^a  

^a UMR 6504   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIAMINONOBORNANE; BORNANE DERIVATIVE; DIAMINE; PLATINUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; PREDICTION;

EID: 33749665414     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.054     Document Type: Article

References (22)

1. Farrell N., De Almeida S.G., and Skov K.A. J. Am. Chem. Soc. 110 (1988) 5018-5019
2. Farrell N., Qu Y., Feng L., and Van Houten B. Biochemistry 29 (1990) 9522-9531
3. Skov K.A., Adomat H., Konway D.C., and Farrell N. Chem. Biol. Interact. 62 (1987) 117-129
4. Kloster M., Kostrhunova H., Zaludova R., Malina J., Kasparkova J., Brabec V., and Farrell N. Biochemistry 43 (2004) 7776-7786
5. Wheate N.J., and Collins J.G. Curr. Med. Chem. Anti-Cancer Agents 5 (2005) 267-279
6. Komeda S., Lutz M., Speck A.L., Chikuma M., and Reedijk J. Inorg. Chem. 39 (2000) 4230-4236
7. Komeda S., Bombard S., Perrier S., Reedijk J., and Kozelka J. J. Inorg. Biochem. 96 (2003) 357-366
8. Magistrato A., Ruggerone P., Spiegel K., Carloni P., and Reedijk J. J. Phys. Chem. B 110 (2006) 3604-3613
9. Ongeri S., Aitken D.J., Husson H.-P., Kozelka J., and Viossat B. Inorg. Chem. 39 (2000) 6131-6133
10. Aitken D.J., Husson H.-P., Nguyen-Huy D., Ongeri S., Vergne F., and Viossat B. Inorg. Chem. Commun. 1 (1998) 314-316
11. Frisch, M. J. et al., Gaussian, Pittsburgh, PA, 1998.
12. 3 was added according to. Wong M.W., Frisch M.J., and Wiberg K.B. J. Am. Chem. Soc. 113 (1991) 4776-4782
13. Previous syntheses: Curtius rearrengement:. Alder K., and Stein G. Justus Liebigs Ann. Chem. 247 (1936) 251-252
14. 4:. Shechter H., Gardikes J.J., Cantrell T.S., and Tiers G.V.D. J. Am. Chem. Soc. 89 (1967) 3005-3014
15. Evans D.A., Faul M.M., and Bilodeau M.T. J. Am. Chem. Soc. 116 (1994) 2742-2753
16. Epoxynorbornane is difficult to open, see:. Grayson S.M., Long B.K., Kusomoto S., Osborn B.P., Callahan R.P., Chambers C.R., and Willson C.G. J. Org. Chem. 71 (2006) 341-344
17. Caution: hydrazoic acid can be released; the reaction should proceed in a fume hood. See:. Demko Z.P., and Sharpless K.B. J. Org. Chem. 66 (2001) 7945-7950 for a safety test
18. CHR22 = 0.60
19. Hatano K., and Saito R. Bull. Chem. Soc. Jpn. 66 (1993) 3818-3821
20. Trans effect of DMSO:. Kukushkin Y.N., Vyaz'menskii Y.E., and Zorina L.I. Russ. J. Inorg. Chem. 13 (1968) 1573-1576
21. 2 C: 16.22%, H: 3.22%, N: 3.44%. Found: C: 16.08%, H: 3.24%, N: 3.53%.
22. Pregosin P.S. Annu. Rep. NMR Spectrosc. 17 (1986) 285-349