Synthesis and biological evaluation of aeroplysinin analogues: a new class of receptor tyrosine kinase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 6, Issue 8, 1998, Pages 1153-1162

  Hinterding, Klaus ^a   Knebel, Axel ^b   Herrlich, Peter ^b   Waldmann, Herbert ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

Aeroplysinin; EGF receptor; Enzyme inhibition; PDGF receptor; Tyrosine kinase

Indexed keywords

AEROPLYSININ DERIVATIVE; EPIDERMAL GROWTH FACTOR RECEPTOR; PLATELET DERIVED GROWTH FACTOR RECEPTOR; PROTEIN TYROSINE KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; AUTOPHOSPHORYLATION; CELL STRAIN 3T3; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SIGNAL TRANSDUCTION;

ACETONITRILES; ANIMALS; CELLS, CULTURED; CYCLOHEXENES; ENZYME INHIBITORS; RATS; RECEPTOR PROTEIN-TYROSINE KINASES; RECEPTOR, EPIDERMAL GROWTH FACTOR; RECEPTORS, PLATELET-DERIVED GROWTH FACTOR;

EID: 0031690667     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)00070-4     Document Type: Article

References (43)

1. (a) Protein phosphorylation; Marks, F., Ed.; VCH: Weinheim 1996.
2. (b) Protein Kinases; Woodgett, J. R., Ed.; Oxford, 1994.
3. (c) Cooper, G. F. Oncogenes, 2nd ed.; Jones and Bartlett: Boston 1995.
4. (a) Levitzki, A.; Gazit, A. Science 1995, 267, 1782.
5. (b) Levitzki, A. Eur. J. Biochem. 1994, 226, 1.
6. (c) Bridges, A. J. Chemtracts - Organic Chemistry 1995, 8, 73.
7. (d) Fry, D. W. Ann. Rep. Med. Chem. 1996, 31, 151.
8. Taylor, S. I.; Cana, A.; Accili, D.; Barbetti, F.; Quon, M. J.; Sierra, M. D.; Suzuki, Y.; Koller, E.; Levytoledano, R.; Wertheimer, E.; Moncada, V. Y.; Kadowaki, H.; Kadowaki, T. Endocr. Rev. 1992, 13, 566.
9. For the use of tyrosine kinase inhibitors in the dissection of signalling pathways see: (a) Daub, H.; Weiss, F. U.; Wallasch, C.; Ullrich, A. Nature 1996, 379, 557.
10. (b) Novogrodsky, A.; Vanichin, A.; Patya, M.; Gazit, A.; Osherov, N.; Levitzki, A. Science 1994, 264, 1319.
11. (c) Meydan, N.; Grünberger, T.; Dadi, H.; Shahar, M.; Arpaia, E.; Lapidot, Z.; Leeder, J. S.; Freedman, M.; Cohen, A.; Gazit, A.; Levitzki, A.; Roifman, C. M. Nature 1996, 379, 645.
12. (d) Dudley, D. T.; Pong, L.; Decker, S. J.; Bridges, A. J.; Saltiel, A. R. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7686.
13. (e) Lepley, R. A.; Kirkpatrick, R. A. Arch. Biochem. Biophys. 1996, 331, 141.
14. (f) Review: Hinterding, K.; Alonso-Díaz, D.; Waldmann, H. Angew. Chem. 1998, 110, 716; Angew. Chem. Int. Ed. Engl. 1998, 37, 688.
15. (f) Review: Hinterding, K.; Alonso-Díaz, D.; Waldmann, H. Angew. Chem. 1998, 110, 716; Angew. Chem. Int. Ed. Engl. 1998, 37, 688.
16. Onoda, T.; Iinuma, H.; Saski, Y.; Hamada, M.; Isshiki, K.; Naganawa, H.; Takeuchi, T.; Tatsuta, K.; Umezawa, K. J. Nat. Prod. 1989, 52, 1252.
17. Glossmann, H.; Presek, P.; Ergenbrodt, E. Naunyn Schmiedeberg's Arch. Pharmacol. 1981, 317, 100.
18. Umezawa, H.; Imoto, M.; Sawar, T.; Isshiki, K.; Matsuda, N.; Uchida, T.; Finuma, H.; Hamada, M.; Takeuchi, T. J. Antibiot. 1986, 39, 170.
19. For recent studies of tyrosine kinase inhibitors see for example: (a) Buchdunger, E.; Zimmermann, J.; Mett, H.; Meyer, T.; Müller, M.; Regenass, U.; Lydon, N. B. Proc. Natl. Acad. Sci., U.S.A. 1995, 92, 2558.
20. (b) Zimmermann, J.; Buchdunger, E.; Mett, H.; Meyer, T.; Lydon, N. B.; Traxler, P. Bioorg. Med. Chem. Lett. 1996, 6, 1221.
21. (c) Kobayashi, J.; Madono, T.; Shigemoni, H. Tetrahedron 1995, 51, 10867.
22. (d) Alvi, K.; Diaz, M. C.; Crews, P.; Slate, D. L.; Lee, R. H.; Moretti, R. J. Org. Chem. 1992, 57, 6604.
23. (a) Rewcastle, G. W.; Palmer, B. D.; Thompson, A. M.; Bridges, A. J.; Cody, D. R.; Zhou, H.; Frey, D. W.; McMichael, A.; Denny, W. A. J. Med. Chem. 1996, 39, 1823.
24. (b) Frey, W.; Kratow, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W. R.; Connors, R. W.; Bridges, A. J. Science 1994, 265, 1093.
25. (c) Spada, A. P.; Myers, M. R. Exp. Opin. Ther. Patents 1995, 5, 805.
26. (d) Bridges, A. J.; Zhou, H.; Cody, D. R.; Rewcastle, G. W.; McMichael, A.; Showalter, H. D. H.; Fry, D. W.; Kraker, A. J.; Denny, W. A. J. Med. Chem. 1996, 39, 267.
27. (e) Traxler, P.; Lydon, N. Drugs Future 1995, 20, 1261.
28. Review: Levitzki, A. FASEB J. 1992, 6, 3275.
29. Kreuter, M.-H.; Leake, R. E.; Rinaldi, F.; Müller-Klieser, W.; Maidhof, A.; Müller, W. E. G.; Schröder, H. C. Comp. Biochem. Physiol. 1990, 978, 151.
30. Part of this work was published in preliminary form: Waldmann, H.; Hinterding, K.; Herrlich, P.; Rahmsdorf, H. J.; Knebel, A. Angew. Chem. 1997, 109, 1553; Angew. Chem. Int. Ed. Engl. 1997, 36, 1541.
31. Part of this work was published in preliminary form: Waldmann, H.; Hinterding, K.; Herrlich, P.; Rahmsdorf, H. J.; Knebel, A. Angew. Chem. 1997, 109, 1553; Angew. Chem. Int. Ed. Engl. 1997, 36, 1541.
32. (+)-Aeroplysinin was kindly supplied by Professor Proksch, Lehrstuhl für Pharmazeutische Biologie, Universität Würzburg.
33. Wasilenko, W. J.; Payne, D. M.; Fitzgerald, D. L.; Weber, M. J. Mol. Cell. Biol. 1991, 11, 309.
34. Becker, H.-D.; Bremholt, T.; Adler, E. Tetrahedron Lett. 1972, 13, 4205. For recent applications of the Becker-Adler oxidation in natural product synthesis see: (a) Corey, E. J.; Dittami, J. P. J. Am. Chem. Soc. 1985, 107, 256.
35. Becker, H.-D.; Bremholt, T.; Adler, E. Tetrahedron Lett. 1972, 13, 4205. For recent applications of the Becker-Adler oxidation in natural product synthesis see: (a) Corey, E. J.; Dittami, J. P. J. Am. Chem. Soc. 1985, 107, 256.
36. (b) Danishefsky, S.; Shair, M. D. J. Org. Chem. 1996, 61, 16.
37. Aldehyde 3 is commercially available.
38. Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis; Wiley, New York 1967, Vol. 1, p 967.
39. Knebel, A.; Rahmsdorf, H. J.; Ullrich, A.; Herrlich, P. EMBO J. 1996, 15, 5314.
40. Synthesis of aeroplysinin and iso-aeroplysinin: Andersen, R. J.; Faulkner, D. J. J. Am. Chem. Soc. 1975, 97, 936.
41. The NIH-3T3-β-PDGFR cells were kindly supplied by Professor Dr A. Ullrich, MPI für Biochemie, Martinsried.
42. Offe, J.; Jatzkewitz, K. Chem. Ber. 1947, 80, 469.
43. Lindemann, J.; Forth, P. J. Liebigs Ann. Chem. 1924, 223.