Novel squalene-hopene cyclase inhibitors derived from hydroxycoumarins and hydroxyacetophenones

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 10, 2004, Pages 1171-1174

  Cravotto, Giancarlo ^a   Balliano, Gianni ^a   Tagliapietra, Silvia ^a   Oliaro Bosso, Simonetta ^a   Nano, Gian Mario ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

4 alkyloxyacetophenone; 7 alkyloxycoumarin; Oxidosqualene cyclase; Secoammoresinol; Secoferulenol; Squalene hopene cyclase

Indexed keywords

1 (2 HYDROXY 4 UNDEC 10 ENYLOXY PHENYL)ETHANONE; 1 [2 HYDROXY 4 (9 OXYRANYL NONYLOXY)PHENYL]ETHANONE; 10 UNDECENOIC ACID 2 OXO 2H CHROMEN 7 YL ESTER; 2 GERANYLSULFANYCHROMEN 4 ONE; 3 (10 UNDECENOYL)CHROMAN 2,4 DIONE; 3 GERANYL 2 MERCAPTOCHROMEN 4 ONE; 4 GERANYLSULFANYLCHROMEN 2 ONE; 7 (10 UNDECENYLOXY)CHROMEN 2 ONE; 7 (9 OXIRANYLNONYLOXY)CHROMEN 2 ONE; 9 OXYRANYLNONANOIC ACID 2 OXO 2H CHROMEN 7 YL ESTER; ACETOPHENONE DERIVATIVE; ALKYL GROUP; COUMARIN DERIVATIVE; EPOXIDE; RESACETOPHENONE; SQUALENE HOPENE CYCLASE INHIBITOR; UMBELLIFERONE; UNCLASSIFIED DRUG; 2,6 DIHYDROXYACETOPHENONE; 2,6-DIHYDROXYACETOPHENONE; MUTASE; SQUALENE HOPENE CYCLASE; SQUALENE-HOPENE CYCLASE; UMBELLIFERONE DERIVATIVE;

ALICYCLOBACILLUS ACIDOCALDARIUS; ARTICLE; DRUG DESIGN; DRUG EFFECT; DRUG STRUCTURE; ESCHERICHIA COLI; INHIBITION KINETICS; MOLECULAR INTERACTION; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION; BACILLACEAE; CHEMISTRY; DRUG ANTAGONISM; SYNTHESIS;

ACETOPHENONES; BACILLACEAE; INTRAMOLECULAR TRANSFERASES; STRUCTURE-ACTIVITY RELATIONSHIP; UMBELLIFERONES;

EID: 11844260816     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.52.1171     Document Type: Article

References (41)

1. Nes W. D., Recent Adv. Phytochem., 24, 283-327 (1990).
2. Abe I., Sankawa U., Ebizuka Y., Chem. Pharm. Bull., 40, 1755-1760 (1992).
3. Moore W. R., Schatzman G. L. J., Biol. Chem., 267, 22003-22006 (1992).
4. Corey E. J., Matzuda S. P. T., J. Am. Chem. Soc., 113, 8172-8174 (1991).
5. Kelly R., Miller S. M., Lai M. H., Kirsch D. R., Gene, 87, 177-183 (1990).
6. Roessner C. A., Min C., Hardin S. H., Harris-Haller L. W., McCollum J. C., Scott A. I., Gene, 127, 149-150 (1993).
7. Lees N. D., Skaggs B., Kirsch D. R., Bard M., Lipids, 30, 221-226 (1995).
8. Baker C. H., Matsuda S. P. T., Liu D. R., Corey E. J., Biochem. Biophys. Res. Commun., 213, 154-160 (1995).
9. Abe I., Prestwich G. D., Proc. Natl. Acad. Sci. U.S.A., 92, 9274-9278 (1995).
10. Abe I., Rohmer M., Prestwich G. D., Chem. Rev., 93, 2189-2206 (1993).
11. Corey E. J., Virgil S. C., Cheng H., Hunter-Baker C., Matsuda S. P. T., Singh V., Sarshar S., J. Am. Chem. Soc., 117, 11819-11820 (1995).
12. Ceruti M., Balliano G., Viola F., Grosa G., Rocco F., Cattel L., J. Med. Chem., 35, 3050-3058 (1992).
13. Ceruti M., Rocco F., Viola F., Balliano G., Milla P., Arpicco S., Cattel L., J. Med. Chem., 41, 540-554 (1998).
14. Abe I., Liu W., Oelhschlager A. C., Prestwich G. D., J. Am. Chem. Soc., 118, 9180-9181 (1996).
15. Jolidon S., Polak-Wyss A., Hartman P. G., Guerry P. G., "Recent Advances in the Chemistry of Anti-infective Agents," Royal Soc. Chem., Cambridge, U.K., 1993, pp. 223-233.
16. Morand O. H., Aebi J. D., Dehlmlow H., Ji Y. H., Gains N., Lengsfeld H., Himber J. J., Lipid Res., 38, 373-390 (1997).
17. Dehlmlow H., Aebi J. D., Jolidon S., Ji Y. H., von der Mark E. M., Himber J., Morand O. H., J. Med. Chem., 46, 3354-3370 (2003).
18. Buckner F. S., Griffin J. H., Wilson A. J., Van Voorhis W. C., Antimicrob. Agents Chemother., 45, 1210-1215 (2001).
19. 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), on May 5-8, 2002.
20. Wendt K. U., Poralla K., Schulz G. E., Science, 277, 1811-1815 (1997).
21. Wendt K. U., Lenhart A., Schulz G. E., J. Mol. Biol., 286, 175-197 (1999).
22. Wendt K. U., Schulz G. E., Corey E. J., Liu D. R., Angew. Chem. Int. Ed., 39, 2821-2833 (2000).
23. Lenhart A., Reinert D. J., Aebi J. D., Dehmlow H., Morand O. H., Schulz G. E., J. Med. Chem., 46, 2063-2092 (2003).
24. Viola F., Ceruti M., Cattel L., Milla P., Poralla, K., Balliano G., Lipids, 35, 297-303 (2000).
25. Ceruti M., Balliano G., Rocco F., Milla P., Arpicco S., Cattel L., Viola F., Lipids, 36, 629-636 (2001).
26. Cravotto G., Balliano G., Robaldo B., Oliaro-Bosso S., Chimichi S., Boccalini M., Bioorg. Med. Chem. Lett., 14, 1931-1934 (2004).
27. Di Braccio M., Roma G., Leoncini G., Poggi M., Farmaco, 50, 703-711 (1995).
28. Majumdar K. C., Biswas A., Mukhopadhyay P. P., Synthesis, 15, 2385-2389 (2003).
29. Cravotto G., Tagliapietra S., Palmisano G., Nano G. M., Heterocycles, 60, 1351-1358 (2003).
30. Grundon M. F., Ramachandran V. N., Donnelly M. E., Perkin Trans 1, 2, 633-635 (1981).
31. Angioni A., Cabras P., D'hallewin G., Pirisi F., M. Reniero F., Schirra M., Phytochemistry, 47, 1521-1525 (1998).
32. Aziz M., Rouessac F., Tetrahedron Lett., 28, 2579-2582 (1987).
33. Pistelli L., Bertoli A., Bilia A. R., Morelli I., Phytochemistry, 41, 1579-1582 (1996).
34. Ganguly N. C., Sukai A. K., Dutta S., De P., J. Ind. Chem. Soc., 78, 380-382 (2001).
35. Al-Yahya M. A., Muhammad I., Mirza H. H., El-Feraly F. S., Phytother. Res., 12, 335-339 (1998).
36. Mizukami H., Ogihara Y., Chem. Pharm. Bull., 46, 1781-1784 (1998).
37. Appendino G., Tagliapietra S., Cravotto G., Nano G. M., Gazz. Chim. Ital., 119, 385-388 (1989).
38. Gonzales A. G., Jorge D., Anales de Quimica, 79, 265-269 (1983).
39. Van Tamelen E. E., Nadeau R. G., J. Am. Chem. Soc., 89, 176-177 (1967).
40. Popják, G., "Methods in Enzymology, Steroids and Terpenoids," Vol. XV, ed. by Clayton R. B., Academic Press, New York, 1969, pp. 438-443.
41. Balliano G., Viola F., Ceruti M., Cattel L., Biochim. Biophys. Acta, 959, 9-19 (1988).