On the conformations of halichlorine and the pinnaic acids: Nitrogen inversion as a possible determinant of biological profile

Helvetica Chimica Acta

Volumn 83, Issue 9, 2000, Pages 2344-2351

  Trauner, Dirk ^a   Churchill, David G ^b   Danisliefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; HALICHLORINE; LACTONE DERIVATIVE; PHOSPHOLIPASE A2; PINNAIC ACID; QUINOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG; VASCULAR CELL ADHESION MOLECULE 1;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; MOLECULAR MODEL; NUCLEAR OVERHAUSER EFFECT; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

EID: 0033787008     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20000906)83:9<2344::AID-HLCA2344>3.0.CO;2-2     Document Type: Article

References (20)

1. a) M. Kuramoto, C. Tong, K. Yamada, T. Chiba, Y. Hayashi, D. Uemura, Tetrahedron Lett. 1996, 37, 3867;
2. b) H. Arimoto, I. Hayakawa, M. Kuramoto, D. Uemura, Tetrahedron Lett. 1998, 39, 861.
3. T. Chou, M. Kuramoto, Y. Onati, K. Yamada, M. Shikano, K. Yazawa, D. Uemura, Tetrahedron Lett. 1996, 37, 3867.
4. a) A. N. Barclay, M. H. Brown, S. K. A. Law, A. J. McKnight, M. G. Tomlinson, P. A. Van der Merwe, 'The Leucocyte Antigen Facts Book', Academic Press: Oxford 1997;
5. b) C. A. Foster, J. Allergy Clin. Immunol. 1996, S272;
6. c) T. A. Springer, Cell 1994, 76, 301;
7. d) T. M. Carlos, J. K. Harlan, Blood 1994, 84, 2068;
8. e) F. Vidal-Vanaclocha, G. Fantuzzi, L. Mendoza, A. M. Fuentes, M. J. Anasagasti, J. Martin, T. Carrascal, P. Walsh, L. L. Reznikov, S.-H. Kim, D. Novick, M. Rubinstein, C. A. Dinarello, Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 734.
9. a) D. Trauner, J. Schwarz, S. J. Danishefsky, Angew. Chem., Int. Ed. 1999, 38, 3542;
10. b) D. Trauner, S. J. Danishefsky, Tetrahedron Lett. 1999, 40, 6511.
11. a) K. Prokai-Tatrai, J. A. Zoltewicz, W. R. Kem, Tetrahedron 1994, 33, 9909;
12. b) J. M. McIntosh, L. C. Matassa, J. Org. Chem. 1988, 53, 4452, and refs. cit. therein;
13. c) E. Gössinger, Monatsh. Chem. 1980, 111, 143;
14. d) E. Wenkert, B. Chauncy, K. G. Dave, A. R. Jeffcoat, F. M. Schell, H. P. Schenk, J. Am. Chem. Soc. 1973, 95, 8427.
15. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440.
16. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
17. J. C. Gilbert, U. Weerasooriya, J. Org. Chem. 1979, 44, 4997.
18. a) R. Keese, M. Meyer, Tetrahedron 1993, 49, 2055;
19. b) M. E. Jung, J. Gervay, J. Am. Chem. Soc. 1991, 113, 224, and refs. cit. therein.
20. S. Lee, Z. Zhao, Org. Lett. 1999, 1, 681.