Natural product synthesis on polymeric supports - Synthesis and biological evaluation of an indolactam library

Angewandte Chemie - International Edition

Volumn 38, Issue 19, 1999, Pages 2902-2906

  Meseguer, Benjamin ^a   Alonso Díaz, Daniel ^a   Griebenow, Nils ^b   Herget, Thomas ^c   Waldmann, Herbert ^a  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b BAYER AG   (Germany)

^c NONE

Author keywords

Alkaloids; Combinatorial chemistry; Drug research; Signal transduction; Total synthesis

Indexed keywords

INDOLACTAM V;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; STRUCTURE ANALYSIS;

EID: 0033523661     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991004)38:19<2902::AID-ANIE2902>3.0.CO;2-2     Document Type: Article

References (46)

1. a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288;
2. a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288;
3. b) J. S. Früchtel, G. Jung, Angew. Chem. 1996, 108, 19; Angew. Chem. Int. Ed. Engl. 1996, 35, 17;
4. b) J. S. Früchtel, G. Jung, Angew. Chem. 1996, 108, 19; Angew. Chem. Int. Ed. Engl. 1996, 35, 17;
5. c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555;
6. d) D. Obrecht, J. M. Villagordo, Solid-supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries, Pergamon, New York, 1998.
7. In a few cases syntheses of natural product based compound libraries have been described. See a) K. C. Nicolaou, N. Winssinger, J. A. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, E. Hansel, Nature 1997, 387, 268;
8. b) K. C. Nicolaou, N. Winssinger, D. Vourloumis, T. Oshima, S. Kim, J. Pfefferkorn, J.-Y. Xu, T. Li, J. Am. Chem. Soc. 1998, 120, 10814;
9. c) K. C. Nicolaou, J. A. Pastor, N. Winssinger, F. Murphy, J. Am. Chem. Soc. 1998, 120, 5132;
10. d) L. A. Thompson, F. L. Moore, Y.-C. Moon, J. A. Ellman, J. Org. Chem. 1998, 63, 2066;
11. e) S. Chen, K. D. Janda, J. Am. Chem. Soc. 1997, 119, 8724;
12. f) J. Nielsen, L. O. Lynsgo, Tetrahedron Lett. 1996, 37, 8439.
13. a) Y. Nishizuka, Science 1986, 233, 305;
14. b) Y. Nishizuka, Science 1992, 258, 607;
15. c) D. Bradshaw, C. H. Hill, J. S. Nixon, S. E. Wilkinson, Agents Actions 1993, 38, 135.
16. For an application of an isoenzyme-selective PKC inhibitor that targets specific tissues, see H. Ishii, M. R. Jirouselz, D. Koya, C. Tatzagi, P. Xia, A. Clermont, S.-E. Bursell, T. S. Kern, L. M. Ballas, W. F. Heath, L. E. Stramm, E. P. Femer, G. L. King, Science 1996, 272, 728.
17. Review: H. Fugitzi, T. Sugimura, Adv. Cancer Res. 1987, 49, 223.
18. a) A. P. Kozikowski, S. Wang, D. Ma, J. Yao, S. Ahmad, R. I. Glazer, K. Bogi, P. Acs, S. Modarres, N. E. Lewin, P. M. Blumberg, J. Med. Chem. 1997, 40, 1316, and references therein;
19. b) I. Irie, T. Isaka, Y. Iwata, Y. Yanai, Y. Nakamura, F. Koizumi, H. Ohigashi, P. A. Wender, Y. Satomi, H. Nishino, J. Am. Chem. Soc. 1996, 118, 10733, and references therein;
20. c) O. A. Moreno, Y. Kishi, J. Am. Chem. Soc. 1996, 118, 8180;
21. d) Y. Endo, M. Hasegawa, A. Itai, K. Shudo, M. Tori, Y. Asakawa, S. Sakai, Tetrahedron Lett. 1985, 26, 1069;
22. e) G. Zhang, M. G. Kazanietz, P. M. Blumberg, J. H. Hurley, Cell 1995, 81, 917;
23. f) I. Irie, S. Okuno, S. Kajiyama, K. Koshimizu, H. Nishino, A. Iwashima, Carcinogenesis 1991, 12, 1883;
24. g) G. Krauter, C. W. Von Der Lieth, R. Schmidt, E. Hecker, Eur. J. Biochem. 1996, 242, 417;
25. h) Y. Endo, M. Ohno, S. Takehana, P. E. Driedger, S. Stabel, K. Shudo, Chem. Pharm. Bull. 1997, 45, 424;
26. i) L. Qiao, S. Wang, C. George, N. E. Lewin, P. M. Blumberg, A. P. Kozikowksi, J. Am. Chem. Soc. 1998, 120, 6629;
27. j) Y. Kishi, R. R. Rando, Acc. Chem. Res. 1998, 31, 163, and references therein.
28. Y. Endo, K. Shudo, A. Itai, M. Hasegawa, S. Sakai, Tetrahedron 1986, 42, 5905.
29. M. Iwao, Heterocycles 1993, 36, 29.
30. K. Nishiyama, N. Tanaka, J. Chem. Soc. Chem. Commun. 1983, 1322.
31. S. Friedrich-Bochnitschek, H. Waldmann, H. Kunz, J. Org. Chem. 1989, 54, 751.
32. M. Nettekoven, M. Psiorz, H. Waldmann, Tetrahedron Lett. 1995, 36, 1425.
33. -1.
34. Total syntheses of indolactam V: T. P. Kogan, T. C. Somers, M. C. Kenuti, Tetrahedron 1990, 46, 6623, and references therein.
35. a) L. A. Thompson, J. A. Ellman, Tetrahedron Lett. 1994, 35, 9333;
36. b) H. P. Hsieh, Y.-T. Wu, S. T. Chen, K.-T. Wang, Chem. Commun. 1998, 649.
37. 2O (95/5).
38. Y. Endo, Y. Sato, K. Shudo, Tetrahedron 1987, 43, 2241.
39. S. Berteina, S. Wendeborn, W. K.-D. Brill, A. De Mesmaeker, Synlett 1998, 676, and references therein.
40. For a similar observation, see F. Persico, B. D. Wuest, J. Org. Chem. 1993, 53, 95.
41. Parallel solid-phase synthesis was performed with a FlexChem reaction block (Robbins Scientific).
42. a) T. Herget, E. Rozengurt, Eur. J. Biochem. 1994, 225, 539;
43. b) T. Herget, S. Broad, E. Rozengurt, Eur. J. Biochem. 1994, 225, 549.
44. a) T. Herget, S. A. Oehrlein, D. J. C. Pappin, E. Rozengurt, P. J. Parker, Eur. J. Biochem. 1995, 233, 448;
45. b) F. Überall, S. Giselbrecht, K. Hellbert, F. Fresser, B. Bauer, M. Gschwendt, H. H. Grunicke, G. Baier, J. Biol. Chem. 1997, 272, 4072.
46. D. R. Olivier, P. J. Parker, J. Cell Physiol. 1992, 240.