Synthesis and protein kinase C inhibitory activities of indane analogs of balanol

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 8, 1996, Pages 973-978

  Hu, Hong ^a   Hollinshead, Sean P ^a   Hall, Steven E ^a   Kalter, Kiyomi ^a   Ballas, Lawrence M ^a  

^a Sphinx Pharmaceuticals Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BALANOL; CYCLIC AMP DEPENDENT PROTEIN KINASE; INDAN DERIVATIVE; ISOENZYME; PROTEIN KINASE C; PROTEIN KINASE C INHIBITOR;

ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; STEREOCHEMISTRY;

EID: 0029935522     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00151-5     Document Type: Article

References (28)

1. Presented in part at the 209th National ACS Meeting, Division of Medicinal Chemistry, Anaheim, CA, April 2-6, 1995, MEDI# 38.
2. (a) Nishizuka, Y. Annu. Rev. Biochem. 1989, 58, 31.
3. (b) Nishizuka, Y. Nature 1988, 334, 661.
4. (c) Asaoka, Y.; Nakamura, S.; Yoshida, K.; Nishizuka, Y. TIBS. 1992, 17, 414.
5. (d) Bradshaw, D.; Hill, C. H.; Nixon, J. S.; Wilkinson, S. E. Agents Actions. 1993, 38, 135.
6. Tritton, T. R.; Hickman, J. A. Cancer Cells 1990, 2, 95.
7. Garland, L. G. Agents Actions Suppl. 1989, 28, 135.
8. Jakobovits, A.; Rosenthal, A.; Capon, D. J. EMBO J. 1990, 9, 1165.
9. Murakawa, K.; Kohno, M.; Yasunari, K.; Hono, T.; Takeda, T. J. Hypertens. Suppl. 1988, 6, S157.
10. Nagao, S.; Seishima, M.; Mori, S.; Nozawa, Y. J. Invest. Dermatol. 1988, 90, 406.
11. Berry, N.; Nishizuka, Y. Eur. J. Biochem. 1990, 189, 205.
12. Kulanthaivel, P.; Hallock, Y. F.; Boros, C.; Hamilton, S. M.; Janzen, W. P.; Ballas, L. W.; Loomis, C. R.; Jiang, J. B.; Katz, B.; Steiner, J. R.; Clardy, J. J. Am Chem. Soc. 1993, 115, 6452.
13. Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994, 59, 5799.
14. (a) Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1994, 59, 5147.
15. (b) Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. submitted.
16. Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402.
17. Defauw, J. M.; Lampe, J. W.; Hu, H.; Lynch, M. P.; Heerding, J. M.; Biggers, C. K.; Menaldino, D. S.; Murphy, M. M.; Hollinshead, S. P.; Hughes, P. F.; Foglesong, R. J.; Johnson, M. G.; Lai, Y.-S.; Janzen, W. P.; Hall, S. E. Presented at the 24th National Medicinal Chemistry Symposium, Salt Lake City, UT, June, 21-25, 1994, abstract # 37.
18. Lai, Y.-S.; Menaldino, D. S.; Nichols, J. B.; Jagdmann, G. E. Jr.; Mylott, F.; Gillespie, J.; Hall, S. E. Bioorg. Med. Chem. Lett. 1995, 5, 2151.
19. 1H NMR, FTIR, mass spectroscopic and elemental analyses. Yields were not optimized. Optical rotations were obtained for all optically active intermediates and indane analogs. The diastereomeric purities of Mosher's esters were determined by HPLC (silica gel, 8% EtOAc in hexane).
20. (a) Zhang, W.; Jacobsen, E. N. J. Org, Chem. 1991, 56, 2296.
21. (b) Jacobsen, E. N.; Zhang, W.; Muci, A. P.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
22. Corey, E. J.; Roper, T. D.; Ishihara, K.; Sarakinos, G. Tetrahedron Lett. 1993, 34, 8399.
23. Hollinshead, S. P.; Nichols, J. B.; Wilson, J. W. J. Org. Chem. 1994, 59, 6703.
24. (a) Kikkawa, U.; Go, M; Komoto, J.; Nishizuka, Y. Biochem. Biophys. Res. Commun. 1986, 135, 636.
25. (b) Basta, P.; Strickland, M. B.; Holmes, W.; Loomis, C. R.; Ballas, L. M.; Burns, D. J. Biochem. Biophys. Acta 1992, 1132, 154.
26. (c) Kashiwada, Y.; Huang, L.; Ballas, L. M.; Jinag, J. B.; Janzen, W. P.; Lee, K-H. J. Med. Chem. 1994, 37, 195.
27. 50 of 0.46, 0.24, and ≫0.50 μM, respectively. Since additional material is not available, we are unable to repeat the experiment with all the PKC isozymes listed in Table I.
28. For asymmetric synthesis of the azepine ring of balanol, see references 11 and 12. For racemic synthesis of the azepine, see Hu, H.; Jagdmann, G. E. Jr.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659.