The isoxazole as a linchpin for molecules that target folded DNA conformations: Selective lateral lithiation and palladation

Tetrahedron Letters

Volumn 43, Issue 43, 2002, Pages 7673-7677

  Han, Xiaochun ^a   Li, Chun ^a   Rider, Kevin C ^a   Blumenfeld, Alex ^a   Twamley, Brendan ^a   Natale, N R ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; ISOXAZOLE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYST; DNA CONFORMATION; MOLECULAR DYNAMICS;

LATEOLABRAX JAPONICUS;

EID: 0037152345     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01845-2     Document Type: Article

References (34)

1. Han X., Natale N.R. J. Heterocycl. Chem. 38:2001;415-418.
2. Zhou P., Mosher M.D., Taylor W.D., Crawford G.A., Natale N.R. Bioorg. Med. Chem. Lett. 7:1997;2455.
3. Boyd M.R. Frei E.J., Freireich E.J., Accomplishments in Oncology. Cancer Therapy: Where Do We Go From Here? 1:1986;68-76 Lippincott, Philadelphia, PA.
4. Boyd M.R. DeVita V.T. Jr., Hellman S., Rosenberg S.A., Cancer: Principles and Practice of Oncology. 3:1989;1-12 Lippincott, Philadelphia, PA.
5. Boyd M.R., Paull K.D., Rubinstein L.R. Vleriote F.A., Corbett T.H., Baker L.H., Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery and Development. 1992;11-34 Kluwer Academic, Hingham, MA.
6. Paull K.D., Shoemaker R.H., Hodes L., Monks A., Scudiero D.A., Rubinstein L., Plowman J., Boyd M.R. J. Natl. Cancer Inst. 81:1989;1088-1092.
7. Dervan P.B. Bioorg. Med. Chem. 9:2001;2215-2235.
8. Paull K.D., Hodes L., Shoemaker R.H., Monks A., Scudiero D.A., Plowman J., Boyd M.R. Proc. Am. Assoc. Cancer Res. 29:1988;488.
9. Bai R., Paull K.D., Herald C.L., Pettit G.R., Hamel E. J. Biol. Chem. 266:1991;15882-15889.
10. Paull K.D., Lin C.M., Malspeis L., Hamel E. Cancer Res. 52:1992;3892-3900.
11. Hodes L., Paull K.D., Koutsoukos A., Rubinstein L.R. J. Biopharm. Stat. 2:1992;31-48.
12. Ren J., Chaires J.B. J. Am. Chem. Soc. 122:2000;424-425.
13. Ren J., Chaires J.B. Biochemistry. 38:1999;16067-16075.
14. Parkinson G.N., Lee M.P.H., Neidle S. Nature. 417:2002;876-880.
15. 2O) were removed. The whole DNA molecule was constrained, the distance between first potassium and C-10 hydrogen was fixed to <4.00 angstrom. After 3000 iterations using steepest descent minimization, the total energy is -69.5315 kcal, electrostatic is -22.5767 kcal and VdW is -46.9548 kcal.
16. Sun D., Thompson B., Cathers B.E., Salazar M., Kerwin S.M., Trent J.O., Jenkins T.C., Neidle S., Hurley L.H. J. Med. Chem. 40:1997;2113-2116.
17. Han H., Cliff C.L., Hurley L.H. Biochemistry. 38:1999;6981-6986.
18. Hurley L.H., Wheelhouse R.T., Sun D., Kerwin S.M., Salazar M., Fedoroff O.Y., Han F.X., Han H., Izbicka E., Von Hoff D.D. Pharmacol. Ther. 85:2000;141-158.
19. Clark R.D., Jahangir A. Org. React. 47:1995;1-314.
20. Natale N.R., Mirzaei Y.R. Org. Prep. Proced. Int. 25:1993;515-556.
21. Burkhart D.J., Zhou P., Blumenfeld A., Twamley B., Natale N.R. Tetrahedron. 57:2001;8039-8046.
22. Natale N.R., Rogers M.E., Staples R., Triggle D.J., Rutledge A. J. Med. Chem. 42:1999;3087.
23. Zhou P., Natale N.R. Tetrahedron Lett. 39:1998;8249-8253.
24. Stenzel J.R., Natale N.R. Synthesis. 1997;1041-1044.
25. Mosher M.D., Natale N.R. J. Heterocylic Chem. 32:1995;1385-1387.
26. Littke A.F., Fu G.C. Angew. Chem., Int. Ed. 37:1998;3387-3388.
27. Littke A.F., Dai C., Fu G.C. J. Am. Chem. Soc. 122:2001;4020-4028.
28. Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483.
29. Brownstein S.K., Ding J., Robertson G., Roovers J. J. Org. Chem. 67:2002;663-667.
30. Coudret C., Mazenc V. Tetrahedron Lett. 38:1997;5293-5296.
31. Wagner G., Herrmann R., Scherer W. J. Organomet. Chem. 516:1996;225-233.
32. Eastwood A.J., Contoret A.E.A., Farrar S.R., Fowler S., Kelly S.M., Khan S.M., Nicholls J.E., O'Neill M. Synth. Met. 121:2001;1659-1660.
33. Baumgarten M., Yeksel T. Phys. Chem. Chem. Phys. 1:1999;1699-1706.
34. 13C NMR, and HR MS or elemental analysis. Selected spectral data