Forskolin studies

Tetrahedron

Volumn 56, Issue 8, 2000, Pages 1081-1095

  Behnke, Dirk ^a   Hennig, Lothar ^a   Findeisen, Matthias ^a   Welzel, Peter ^a   Müller, Dietrich ^b   Thormann, Michael ^a   Hofmann, Hans Jörg ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

Adenylyl cyclase; Forskolin intermediate; Nucleophilic isoprenoid C5 reagent

Indexed keywords

ADENYLATE CYCLASE; FORSKOLIN; FORSKOLIN DERIVATIVE; ISOPRENOID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME BINDING; OPTICAL ROTATION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0034681402     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00005-3     Document Type: Article

References (48)

1. For leading references and studies on the interaction of forskolin on P-glycoprotein, see Morris, D. I.; Greenberger, L. M.; Bruggemann, E. P.; Cardarelli, C.; Gottesman, M. M.; Pastan, I.; Seamon, K. B. Mol. Pharmacol. 1994, 46, 329-337.
2. Yan S.-Z., Hahn D., Huang Z.-H., Tang W.-J. J. Biol. Chem. 271:1996;10 941-10 945.
3. Whisnant, R. E.; Gilman, A. G.; Dessauer, C. W. Proc. Natl. Acad. Sci. 1996, 93, 6621-6625, and references therein.
4. Zhang G., Liu Y., Ruoho A.E., Hurley J.H. Nature. 386:1997;247-253.
5. Tesmer J.J.G., Sunahara R.K., Gilman A.G., Sprang S.R. Science. 278:1997;1907-1916.
6. For leading references, see Colombo, M. I.; Zinczuk, J.; Ruveda, E. A. Tetrahedron 1992, 48, 963-1037; Calvo, D.; Port, M.; Delpech, B.; Lett, R. Tetrahedron Lett. 1996, 37, 1023-1024; Pancrazi, A.; Lallemand, J.-Y.; Prangé, T. Bull. Soc. Chim. Fr. 1997, 134, 203-222.
7. For leading references, see Colombo, M. I.; Zinczuk, J.; Ruveda, E. A. Tetrahedron 1992, 48, 963-1037; Calvo, D.; Port, M.; Delpech, B.; Lett, R. Tetrahedron Lett. 1996, 37, 1023-1024; Pancrazi, A.; Lallemand, J.-Y.; Prangé, T. Bull. Soc. Chim. Fr. 1997, 134, 203-222.
8. For leading references, see Colombo, M. I.; Zinczuk, J.; Ruveda, E. A. Tetrahedron 1992, 48, 963-1037; Calvo, D.; Port, M.; Delpech, B.; Lett, R. Tetrahedron Lett. 1996, 37, 1023-1024; Pancrazi, A.; Lallemand, J.-Y.; Prangé, T. Bull. Soc. Chim. Fr. 1997, 134, 203-222.
9. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olsen, A. J. J. Comput. Chem. 1998, 19, 1639-1662.
10. Cf. Ref. 7 and literature cited therein.
11. Review: Seamon, K. B.; Daly, J. W. Adv. Cyclic Nucleotide Res., 1996, 20, 1-150.
12. For the introduction of the 9-OH group see Hrib, N. J. Tetrahedron Lett. 1987, 28, 19-22; Scherkenbeck, J.; Böttger, D.; Welzel, P. Tetrahedron 1987, 43, 3797-3802; Khandelwal, Y. Jotwani, B. R.; Inamdar, P. K.; de Souza, N. J.; Rupp, R. H. Tetrahedron 1989, 45, 763-766.
13. For the introduction of the 9-OH group see Hrib, N. J. Tetrahedron Lett. 1987, 28, 19-22; Scherkenbeck, J.; Böttger, D.; Welzel, P. Tetrahedron 1987, 43, 3797-3802; Khandelwal, Y. Jotwani, B. R.; Inamdar, P. K.; de Souza, N. J.; Rupp, R. H. Tetrahedron 1989, 45, 763-766.
14. For the introduction of the 9-OH group see Hrib, N. J. Tetrahedron Lett. 1987, 28, 19-22; Scherkenbeck, J.; Böttger, D.; Welzel, P. Tetrahedron 1987, 43, 3797-3802; Khandelwal, Y. Jotwani, B. R.; Inamdar, P. K.; de Souza, N. J.; Rupp, R. H. Tetrahedron 1989, 45, 763-766.
15. For the microbial oxidation at C-1, see Aretz, W.; Böttger, D.; Sauber, K. Biol. Chem. Hoppe-Seyler 1986, 367 (suppl. 213); Nadkarni, S. R.; Akut, P. M.; Ganguli, B. N.; Khandelwal, Y.; de Souza, N. J.; Rupp, R. H.; Fehlhaber, H. W. Tetrahedron Lett. 1986, 27, 5265-5268, see also Fraga, B. M.; Gonzáles, P.; Guillermo, R.; Hernández, G. Tetrahedron 1998, 54, 6159-6168.
16. For the microbial oxidation at C-1, see Aretz, W.; Böttger, D.; Sauber, K. Biol. Chem. Hoppe-Seyler 1986, 367 (suppl. 213); Nadkarni, S. R.; Akut, P. M.; Ganguli, B. N.; Khandelwal, Y.; de Souza, N. J.; Rupp, R. H.; Fehlhaber, H. W. Tetrahedron Lett. 1986, 27, 5265-5268, see also Fraga, B. M.; Gonzáles, P.; Guillermo, R.; Hernández, G. Tetrahedron 1998, 54, 6159-6168.
17. For the microbial oxidation at C-1, see Aretz, W.; Böttger, D.; Sauber, K. Biol. Chem. Hoppe-Seyler 1986, 367 (suppl. 213); Nadkarni, S. R.; Akut, P. M.; Ganguli, B. N.; Khandelwal, Y.; de Souza, N. J.; Rupp, R. H.; Fehlhaber, H. W. Tetrahedron Lett. 1986, 27, 5265-5268, see also Fraga, B. M.; Gonzáles, P.; Guillermo, R.; Hernández, G. Tetrahedron 1998, 54, 6159-6168.
18. Bick S., Zimmermann S., Meuer H., Sheldrick W.S., Welzel P. Tetrahedron. 49:1993;2457-2468.
19. See Narula, A. S. Tetrahedron Lett. 1982, 23, 5579-5582, and references therein.
20. Zimmermann S., Bick S., Welzel P., Meuer H., Sheldrick W.S. Tetrahedron. 51:1995;2947-2952.
21. For leading references, see McKee, B. H.; Kalantar, T. H.; Sharpless, K. B. J. Org. Chem. 1991, 56, 6966-6968.
22. Jordine G., Bick S., Möller U., Welzel P., Daucher B., Maas G. Tetrahedron. 50:1994;139-160.
23. Cf.Depew K.M., Danishefsky S.J., Rosen N., Sepp-Lorenzino L. J. Am. Chem. Soc. 118:1996;12 463-12 464.
24. Nájera C., Yus M., Seebach D. Helv. Chim. Acta. 67:1984;289-300.
25. Barluenga, J.; Flórez, J.; Yus, M. J. Chem. Soc. Perkin Trans. 1 1983, 3019-3026; Barluenga, J.; Fernández-Simon, J. L.; Concellón, J. M.; Yus, M. J. Chem. Soc. Perkin Trans. 1 1988, 3339-3343.
26. Barluenga, J.; Flórez, J.; Yus, M. J. Chem. Soc. Perkin Trans. 1 1983, 3019-3026; Barluenga, J.; Fernández-Simon, J. L.; Concellón, J. M.; Yus, M. J. Chem. Soc. Perkin Trans. 1 1988, 3339-3343.
27. Wittmann, V.; Kessler, H. Angew. Chem. 1993, 105, 1138-1140; Angew. Chem., Int. Ed. Engl. 1993, 32. 1091-1093.
28. Wittmann, V.; Kessler, H. Angew. Chem. 1993, 105, 1138-1140; Angew. Chem., Int. Ed. Engl. 1993, 32. 1091-1093.
29. Review: Marshall, J. A. Chem. Rev. 1996, 96, 31-47.
30. Review: Carey, J. S.; Coulter, T. S.; Hallett, D. J.; Maguire, R. J.; McNeill, A. H.; Stanway, S. J.; Teerawutgulrag, A.; Thomas, E. J. Pure Appl. Chem. 1996, 68 707-710.
31. Behnke D., Hamm S., Hennig L., Welzel P. Tetrahedron Lett. 38:1997;7059-7062.
32. For a preliminary account of this work, see Ref. 23.
33. Marshall J.A., Hinkle K.W. J. Org. Chem. 61:1996;105-108.
34. A preliminary account of this work has appeared, see Ref. 18.
35. Holton R.A., Juo R.R., Kim H.B., Williams A.D., Harusawa S., Lowenthal R.E., Yogai S. J. Am. Chem. Soc. 110:1988;6558-6560.
36. Barluenga J., Fañanás F.J., Yus M. J. Org. Chem. 44:1979;4798-4801.
37. Barluenga J., Fañanás F.J., Villamaña J., Yus M. J. Org. Chem. 47:1982;1560-1564.
38. Cohen T., Jeong I.-H., Mudryk B., Bhupathy M., Awad M.A. J. Org. Chem. 55:1990;1528-1536.
39. Bachki A., Foubelo F., Yus M. Tetrahedron: Asymmetry. 7:1996;2997-3008.
40. Yus M., Ramón D.J. J. Chem. Soc., Chem. Commun. 1991;398-400.
41. Screttas C.G., Micha-Screttas M. J. Org. Chem. 44:1979;713-719.
42. Cohen T., Weisenfeld R.B. J. Org. Chem. 44:1979;3601-3603.
43. Freeman P.K., Hutchinson L.L. J. Org. Chem. 48:1983;4705-4713.
44. Freeman P.K., Hutchinson L.L. Tetrahedron Lett. 1976;1849-1852.
45. Review: Yus, M. Chem. Soc. Rev. 1996, 155-161.
46. Still W.C., Kahn M., Mitra A. J. Org. Chem. 43:1978;2923-2925.
47. Kritchevsky D., Kirk M.R. Arch. Biochem. Biophys. 35:1952;346-351.
48. 12.