Flavonoids and cinnamic acid esters as inhibitors of fungal 17β-hydroxysteroid dehydrogenase: A synthesis, QSAR and modelling study

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 22, 2006, Pages 7404-7418

  Sova, Matej ^a   Perdih, Andrej ^a   Kotnik, Miha ^b   Kristan, Katja ^a   Rižner, Tea Lanišnik ^a   Solmajer, Tom ^b,c   Gobec, Stanislav ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b Lek dd   (Slovenia)

^c NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

Author keywords

17 Hydroxysteroid dehydrogenases; Anticancer agents; Inhibitors; Molecular modelling

Indexed keywords

(1,3 DIOXOISOINDOLIN 2 YL)METHYL 2 (BENZO[D][1,3]DIOXOL 6 YL)ACETATE; (1,3 DIOXOISOINDOLIN 2 YL)METHYL 2 OXO CHROMENE 3 CARBOXYLATE; (1,3 DIOXOISOINDOLIN 2 YL)METHYL 3 (3,4,5 TRIMEETHOXYPHENYL)ACRYLATE; 1 NAPHTHYL 3 (3,4,5 TRIMETHOXY PHENYL)ACRYLATE; 1 NAPHTHYL CINNAMATE; 2 (1,3 DIOXOISOINDOLIN 2 YL) ETHYL CINNAMATE; 2 (1,3 DIOXOISOINDOLIN 2 YL)ETHYL 2 OXO CHROMENE 3 CARBOXYLATE; 2 (1,3 DIOXOISOINDOLIN 2 YL)ETHYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLATE; 3 METHOXYPHENYL CINNAMATE; 3 PHENOXYPHENYL CINNAMATE; 3,4,5 TRIMETHOXYBENZYL 2 (BENZO[D][1,3] DIOXOL 6 YL)ACETATE; 3,4,5 TRIMETHOXYBENZYL 3 (3,4 DIHYDROXY PHENYL)ACRYLATE; 3,4,5 TRIMETHOXYBENZYL CINNAMATE; 3,4,5 TRIMOETHOXYBENZYL 2 OXO CHROMENE 3 CAYBOXYLATE; 4 (OCTANAMIDO)PHENYL CINNAMATE; 4 ACETAMIDOPHENYL CINNAMATE; 4 CYANOPHENYL CINNAMATE; ANTIFUNGAL AGENT; AROMATIC AMINO ACID; BENZYL 2 OXO CHROMENE 3 CARBOXYLATE; BENZYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLATE; CINNAMIC ACID BENZYL ESTER; CINNAMIC ACID DERIVATIVE; CYCLOHEXYL CINNAMATE; FLAVONOID; PHENYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLATE; PHENYL CINNAMATE; TESTOSTERONE 17BETA DEHYDROGENASE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CHROMATOGRAPHY; COCHLIOBOLUS; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR RECOGNITION; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

17-HYDROXYSTEROID DEHYDROGENASES; BINDING SITES; CINNAMATES; ESTERS; FLAVONOIDS; FUNGI; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; HYDROPHOBICITY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33749267261     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.07.027     Document Type: Article

References (52)

1. Penning T.M. Endocr. Rev. 18 (1997) 281
2. Mindnich R., Möller G., and Adamski J. Mol. Cell. Endocrinol. 218 (2004) 7
3. Lukacik P., Kavanagh K.L., and Oppermann U. Mol. Cell. Endocrinol. 248 (2006) 61
4. Bros W., Heller W., and Michel C. In: Rice-Evans C.A., and Packer L. (Eds). Flavonoids in Health and Disease (1998), Marcel Dekker, New York 111-136
5. Middelton Jr. E., Kandaswami C., and Theoharides T.C. Pharmacol. Rev. 52 (2000) 673
6. Tham D.M., Christopher D., Gardner D., and Haskell W.L. J. Clin. Endocrinol. Metab. 83 (1998) 2223
7. Ososki A.L., and Kennelly E.J. Phytother. Res. 17 (2003) 845
8. Le Bail J.-C., Champavier Y., Chulia A.-J., and Habrioux G. Life Sci. 66 (2000) 1281
9. Kirk C.J., Harris R.M., Wood D.M., Waring R.H., and Hughes P.J. Biochem. Soc. Trans. 29 (2001) 209
10. Ohno S., Matsumoto N., Watanabe M., and Nakajin S. J. Steroid Biochem. Mol. Biol. 88 (2004) 175
11. Ohno S., Shinoda S., Toyoshima S., Nakazawa H., Makino T., and Nakajin S. J. Steroid Biochem. Mol. Biol. 80 (2002) 355
12. Lephart E.D., Lund T.D., and Horvath T.L. Brain Res. Rev. 37 (2001) 25
13. Weber K.S., Jacobson N.A., Setchell K.D., and Lephart E.D. Proc. Soc. Exp. Biol. Med. 221 (1999) 131
14. Schweizer R.A., Atanasov A.G., Frey B.M., and Odermatt A. Mol. Cell. Endocrinol. 212 (2003) 41
15. Le Lain R., Nicholls P.J., Smith H.J., and Mahrlouie F.H. J. Enzyme Inhib. 16 (2001) 35
16. Le Lain R., Barrell K.J., Saeed G.S., Nicholls P.J., Simons C., Kirby A., and Smith H.J. J. Enzyme Inhib. 17 (2002) 93
17. Le Bail J.-C., Pouget C., Fagnere C., Basly J.-P., Chulia A.-J., and Habrioux G. Life Sci. 68 (2001) 751
18. Makela S., Poutanen M., Lehtimaki J., Kostian M.-L., Santii R., and Vihko R. Proc. Soc. Exp. Biol. Med. 208 (1995) 51
19. Makela S., Poutanen M., Kostian M.L., Lehtimaki N., Strauss L., Santii R., and Vihko R. Proc. Soc. Exp. Biol. Med. 217 (1998) 310
20. Krazeisen A., Breitling R., Moeller G., and Adamski J. Mol. Cell. Endocrinol. 171 (2001) 151
21. Krazeisen A., Breitling R., Moeller G., and Adamski J. Adv. Exp. Med. Biol. 505 (2002) 151
22. Poirier D. Curr. Med. Chem. 10 (2003) 453
23. Kristan K., Krajnc K., Konc J., Gobec S., Stojan J., and Lanišnik Rižner T. Steroids 70 (2005) 626
24. Heller W., and Forkmann G. In: Harborne J.D. (Ed). The Flavonoids. Advances in Research since 1986 (1993), Chapman and Hall Ltd., London 499-535
25. Gobec S., Sova M., Kristan K., and Lanišnik Rižner T. Bioorg. Med. Chem. Lett. 14 (2004) 3933
26. Oblak M., Randic M., and Solmajer T. J. Chem. Inf. Comput. Sci. 40 (2000) 994
27. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 2nd Ed. (1991), John Wiley and Sons, New York
28. Kocienski P.J. Protecting Groups (1994), Georg Thieme, Stuttgart
29. Castro B., Evin G., Selve C., and Seyer R. Synthesis-Stuttgart 6 (1977) 413
30. Lanišnik Rižner T., Moeller G., Thole H.H., Žakelj-Mavrič M., and Adamski J. Biochem. J. 337 (1999) 425
31. Allan G.M., Lawrence H.R., Cornet J., Bubert C., Fischer D.S., Vicker N., Smith A., Tutill H.J., Purohit A., Day J.M., Mahon M.F., Reed M.J., and Potter B.V. J. Med. Chem. 49 (2006) 1325
32. Deluca D., Moller G., Rosinus A., Elger W., Hillisch A., and Adamski J. Mol. Cell. Endocrinol. 248 (2006) 218
33. Kotnik M., Oblak M., Humljan J., Gobec S., Urleb U., and Solmajer T. QSAR Comb. Sci. 23 (2004) 399
34. Solmajer T., and Zupan J. Drug Disc. Today Technol. 1 (2004) 247
35. Homology model of 17-β HSDcl was downloaded from the web site: .
36. Cassetta A., Budefeld T., Rizner T.L., Kristan K., Stojan J., and Lamba D. Acta Crystallogr. Sect. F 61 (2005) 1032
37. Oppermann U., Filling C., Hult M., Shafgat N., Wu X., Lindh M., Shafqat J., Nordling E., Kallberg Y., Persson B., and Jörnvall H. Chem. Biol. Interact. 143/144 (2003) 247
38. Kunishima M., Kawachi C., Morita J., Terao K., Iwasaki F., and Tani S. Tetrahedron 55 (1999) 13159
39. Fuson R.C., and Thomas N. J. Org. Chem. 18 (1953) 1762
40. Dittert L.W., Caldwell H.C., Adams H.J., Irwin G.M., and Swintosky J.V. J. Pharm. Sci. 57 (1968) 774
41. Krajniak E.R., Ritchie E., and Taylor W.C. Aust. J. Chem. 26 (1973) 899
42. Akai S., Tsuzuki Y., Satoshi M., Kitagaki S., and Kita Y. J. Chem. Soc., Perkin Trans. 1 (1992) 2813
43. Orita M., Yamamoto S., Katayama N., Motonori A., Takayama K., Yamagiwa Y., Seki N., Suzuki H., Kurihara H., Sakashita H., Takeuchi M., Fujita S., Yamada T., and Tanaka A. J. Med. Chem. 44 (2001) 540
44. Ulibarri G., Choret N., and Bigg D.C.H. Synthesis (1996) 1286
45. Spartan 5.0 Wavefunction. In Irvine, CA, USA.
46. Steward, J. J. P. MOPAC 93 annual revision Number 2, Fujitsu 1993.
47. Katritzky, A.; Lobanov, V. S.; Karelson, M. CODESSA, Reference manual, Gainsville, 1995.
48. Katritzky, A.; Lobanov, V. S.; Karelson, M. CODESSA, Training manual, Gainsville, 1995.
49. Topliss J.G., and Costello R.J. J. Med. Chem. 15 (1972) 1066
50. Sybyl 7.0, Tripos software, St. Louis, USA.
51. Insight II, Accelrys software, San Diego, CA, USA.
52. McGovern S., Helfand B.T., Feng B., and Shoichet B.K. J. Med. Chem. 46 (2003) 4265