Synthesis and protein kinase C inhibitory activities of balanol analogues with modification of 4-hydroxybenzamido moiety

Bioorganic and Medicinal Chemistry

Volumn 5, Issue 9, 1997, Pages 1873-1882

  Hu, Hong ^a   Mendoza, Jose S ^a   Lowden, Christopher T ^a   Ballas, Lawrence M ^a   Janzen, William P ^a  

^a Sphinx Pharmaceuticals Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BALANOL; BALANOL DERIVATIVE; PROTEIN KINASE C; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CONFORMATION; DRUG SYNTHESIS; ENZYME INHIBITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BACULOVIRIDAE; ENZYME INHIBITORS; HUMANS; ISOENZYMES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PROTEIN KINASE C; RECOMBINANT PROTEINS; SPECTROPHOTOMETRY, INFRARED; SPODOPTERA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030866321     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)00125-9     Document Type: Article

References (27)

1. (a) Farago, A.; Nishizuka, Y. FEBS Lett. 1990, 268, 350.
2. (b) Nishizuka, Y. Nature (London) 1988, 334, 661.
3. (c) Nishizuka, Y. Science 1986, 305.
4. Bradshaw, D.; Hill, C. H.; Nixon, J. S.; Wilkinson, S. E. Agents Actions 1993, 38, 135.
5. Hu, H. Drug Discovery Today 1996, 1, 438.
6. 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.
7. (a) Hughes, P. F.; Smith, S. H.; Olson, J. T. J. Org. Chem. 1994,59, 5799.
8. (b) Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1994, 59, 5147.
9. (c) Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1996, 61, 4572.
10. Hu, H.; Jagdmann, G. E. Jr.; Hughes, P. F.; Nichols, J. B. Tetrahedron Lett. 1995, 36, 3659.
11. (a) Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402.
12. (b) Nicolaou, K. C.; Koide, K.; Bunnage, M. E. Chem. Eur. J. 1995, 1, 454.
13. Tanner, D.; Almario, A.; Hogberg, T. Tetrahedron 1995, 5, 6061.
14. Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem. Soc. Perkin Trans 1 1995, 2355.
15. (a) 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.
16. (b) Lai, Y.-S.; Mendoza, J. S.; Jagdmann, G. E. Jr., Menaldino, D. S; Biggers, C. K.; Heerding, J. M.; Wilson, J. W.; Hall, S. E.; Jiang, J. B.; Janzen, W. P.; Ballas, L. M. J. Med. Chem. 1997, 40, 226.
17. Mendoza, J. S.; Jagdmann, G. E. Jr.; Gosnell, P. A. Bioorg. Med. Chem. Lett. 1995, 5, 2211.
18. Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K. Bioorg. Med. Chem. Lett. 1996, 6, 973-978.
19. Defauw, J. M.; Murphy, M. M.; Jagdmann Jr, G. E.; Hu, H.; Lampe, J. W.; Hollinshead, S. P.; Mitchell, T. J.; Crane, H. M.; Heerding, J. M.; Mendoza, J. S.; Davis, J. E.; Darges, J. W.; Hubbard, F. R., Hall, S. E. J. Med. Chem. 1996, 39, 5215.
20. 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 no. 37.
21. Synthesis of 16a see refs 5b and 6. Synthesis of 16b and 20 see ref. 10.
22. Hollinshead, S. P.; Nichols, J. B.; Wilson, J. W. J. Org. Chem. 1994, 59, 6703.
23. Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Chemistry & Biolology 1995, 2, 601.
24. Basta, P.; Strickland, M. B.; Holmes, W.; Loomis, C. R.; Ballas, L. M.; Burns, D. J. Biochem. Biophys. Acta 1992, 1132, 154.
25. Bronson, D. D.; Daniels, D. M.; Dixon, J. T.; Redick, C. C.; Haaland, P. D. Biochemical Pharmacology 1995, 50, 823.
26. Kochs, G.; Hummel, R.; Fiebich, B.; Sarre, T. F.; Marme, D.; Hug, H. Biochem. J. 1993, 297, 627.
27. Hannun, Y. A.; Loomis, C. R.; Merrill, A. H.; Bell, R. M. J. Biol. Chem. 1986, 261, 12604.