Farnesyloxycoumarins, a new class of squalene-hopene cyclase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 8, 2004, Pages 1931-1934

  Cravotto, Giancarlo ^a   Balliano, Gianni ^a   Robaldo, Bruna ^a   Oliaro Bosso, Simonetta ^a   Chimichi, Stefano ^b   Boccalini, Marco ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Oxidosqualene cyclase; Prenylcoumarins; Selective epoxydation; Squalene hopene cyclase; Umbelliprenin

Indexed keywords

AMMORESINOL; BACTERIAL ENZYME; BADRAKEMON; COLLADIN; COLLADONIN; COUMARIN DERIVATIVE; ENZYME INHIBITOR; EPOXIDE; FARNESYLFEROL C; FERULENOL; KATARAVICINOL; PLANT EXTRACT; SAMARCANDIN; SAMARCANDON; SQUALENE DERIVATIVE; UMBELLIPRENIN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SCREENING; ENZYME INHIBITION; FENNEL; IC 50; NONHUMAN; PROTEIN PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION;

BACILLACEAE; COUMARINS; ENZYME ACTIVATION; ENZYME INHIBITORS; HUMANS; INTRAMOLECULAR TRANSFERASES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 1642588143     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.01.085     Document Type: Article

References (50)

1. Abe, I.; Prestwich, G. D. In Comprehensive Natural Products Chemistry. Isoprenoids Including Carotenoids and Steroids, 1st ed.; Cane, D., Ed.; Elsevier Science Ltd.: Oxford, 1999; Vol. 2, pp 267-298.
2. Brown G.D. Nat. Prod. Rep. 15:1998;653.
3. Kita T. Card. Pract. 13:2002;269.
4. Reinhardt S.C., Vaughan C.J. Drugs Today. 38:2002;339.
5. Monk J.P., Brogden R.N. Drugs. 42:1991;659.
6. McClellan K.J., Wiseman L.R., Markham A. Drugs. 58:1999;179.
7. Vanden Bossche H., Mariachal P., Le Jeune L., Coene M.-C., Gorreas J., Cools W. Antimicrob. Agents Chemother. 37:1993;2101.
8. Vanden Bossche H., Mariachal P., Odds F.C., Le Jeune L., Coene M.-C. Antimicrob. Agents Chemother. 36:1992;2602.
9. Yoshida Y., Aoyama Y. Chirality. 2:1990;10.
10. Nes W.D. Recent Adv. Phytochem. 24:1990;283.
11. Abe I., Sankawa U., Ebizuka Y. Chem. Pharm. Bull. 40:1992;1755.
12. Moore W.R., Schatzman G.L. J. Biol. Chem. 267:1992;22003.
13. Corey E.J., Matzuda S.P.T. J. Am. Chem. Soc. 113:1991;8172.
14. Kelly R., Miller S.M., Lai M.H., Kirsch D.R. Gene. 87:1990;177.
15. Roessner C.A., Min C., Hardin S.H., Harris-Haller L.W., McCollum J.C., Scott A.I. Gene. 127:1993;149.
16. Lees N.D., Skaggs B., Kirsch D.R., Bard M. Lipids. 30:1995;221.
17. Baker C.H., Matsuda S.P.T., Liu D.R., Corey E. J. Biochem. Biophys. Res. Commun. 213:1995;154.
18. Abe I., Prestwich G.D. Proc. Natl. Acad. Sci. U.S.A. 92:1995;9274.
19. Abe I., Rohmer M., Prestwich G.D. Chem. Rev. 93:1993;2189.
20. Corey E.J., Virgil S.C., Cheng H., Hunter-Baker C., Matsuda S.P.T., Singh V., Sarshar S. J. Am. Chem. Soc. 117:1995;11819.
21. Ceruti M., Balliano G., Viola F., Grosa G., Rocco F., Cattel L. J. Med. Chem. 35:1992;3050.
22. Ceruti M., Rocco F., Viola F., Balliano G., Milla P., Arpicco S., Cattel L. J. Med. Chem. 41:1998;540.
23. Abe I., Liu W., Oehlschlager A.C., Prestwich G.D. J. Am. Chem. Soc. 118:1996;9180.
24. Jolidon, S.; Polak-Wyss, A.; Hartman, P. G.; Guerry, P. G. In Recent Advances in the Chemistry of Anti-infective Agents. Royal Soc. Chem.; Cambridge, 1993; p 223.
25. Morand O.H., Aebi J.D., Dehmlow H., Ji Y.H., Gains N., Lengsfeld H., Himber J. J. Lipid Res. 38:1997;373.
26. Dehmlow H., Aebi J.D., Jolidon S., Ji Y.H., von der Mark E.M., Himber J., Morand O.H. J. Med. Chem. 46:2003;3354.
27. Buckner F.S., Griffin J.H., Wilson A.J., Van Voorhis W.C. Antimicrob. Agents Chemother. 45:2001;1210.
28. Oliaro Bosso, S.; Ceruti, M.; Balliano, G.; Matsuda, S. P. T.; Milla, P. ; Rocco, F.; Viola, F. 93rd AOCS Annual Meeting & Expo., Montreal, Quebec, Canada, May 5-8, 2002.
29. Wendt K.U., Poralla K., Schulz G.E. Science. 277:1997;1811.
30. Wendt K.U., Lenhart A., Schulz G.E. J. Mol. Biol. 286:1999;175.
31. Wendt K.U., Schulz G.E., Corey E.J., Liu D.R. Angew. Chem., Int. Ed. 39:2000;2812.
32. Lenhart A., Reinert D.J., Aebi J.D., Dehmlow H., Morand O.H., Schulz G.E. J. Med. Chem. 46:2003;2063.
33. Viola F., Ceruti M., Cattel L., Milla P., Poralla K., Balliano G. Lipids. 35:2000;297.
34. Ceruti M., Balliano G., Rocco F., Milla P., Arpicco S., Cattel L., Viola F. Lipids. 36:2001;629.
35. El-Razek M.H.A., Ohta S., Ahmed A.A., Hirata T. Phytochemistry. 58:2001;1289. and references therein.
36. Eigner D., Scholz D. J. Ethnopharmacol. 67:1999;1.
37. Appendino G., Tagliapietra S., Cravotto G., Nano G.M. Gazz. Chim. Ital. 119:1989;385.
38. Kunz K., Weidle H., Fischer K. J. Prakt. Chem. 141:1934;350.
39. Cravotto G., Chimichi S., Robaldo B., Boccalini M. Tetrahedron Lett. 44:2003;8383.
40. Sato T., Hoshino T. Biosci. Biotechnol. Biochem. 63:1999;1171.
41. van Tamelen E.E., Nadeau R.G. Bioorg. Chem. 11:1982;197.
42. van Tamelen E.E., Curphey T.J. Tetrahedron Lett. 1962;121.
43. Onoda T., Shirai R., Koiso Y., Iwasaki S. Tetrahedron. 52:1996;14543.
44. Al-Ajlouni A., Espenson J.H. J. Am. Chem. Soc. 117:1995;9243.
45. Rudolph J., Reddy K.L., Chiang J.P., Sharpless K.B. J. Am. Chem. Soc. 119:1997;6189.
46. Boehlow T.R., Spilling C.D. Tetrahedron Lett. 37:1996;2717.
47. 2 adduct (2.5 mmol), after 3 h stirring at 20°C we obtained the corresponding 6′,7′:10′,11′- diepoxide as major product. Mono- and diepoxide were easily separed by column chromatography (hexane/EtOAc 9:1 v/v).
48. 50.
49. Popják, G. In Methods in Enzymology, Steroids and Terpenoids. Clayton, R. B., Ed.; Academic Press: New York, 1969; Vol. XV, pp 438-443.
50. Balliano G., Viola F., Ceruti M., Cattel L. Biochim. Biophys. Acta. 959:1988;9.