Trifluoromethyl-substituted hydantoins, versatile building blocks for rational drug design

Tetrahedron

Volumn 60, Issue 19, 2004, Pages 4295-4302

  Wehner, Volkmar ^a   Stilz, Hans Ulrich ^a   Osipov, Sergej N ^b   Golubev, Alexander S ^b   Sieler, Joachim ^c   Burger, Klaus ^c  

^a SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

4+1 Cycloaddition reactions; Domino reactions; Lipophilic building blocks; Retro ene reaction

Indexed keywords

3 [2 [4,4 BIS(TRIFLUOROMETHYL) 3 [4 [ 3 (2 METHYLPHENYL)UREIDO] 3 METHOXYBENZYL] 2,5 DIOXOIMIDAZOLIDIN 1 YL] 2 (CYCLOPROPYLMETHYL)ACETYLAMINO] 3 PHENYLPROPIONIC ACID; ANTIINFLAMMATORY AGENT; HEXAFLUOROACETONE; HYDANTOIN DERIVATIVE; IMINE; PEPTIDE; PYRUVIC ACID DERIVATIVE; TERT BUTYL 2 [4,4 BIS(TRIFLUOROMETHYL) 2,5 DIOXO 1,3 IMIDAZOLIN 1 YL] 2 (CYCLOPROPYLMETHYL)ACETATE; TERT BUTYL 2 [4,4 BIS(TRIFLUOROMETHYL) 2,5 DIOXO 1,3 IMIDAZOLIN 1 YL] 2 (METHYLPROPYL)ACETATE; UNCLASSIFIED DRUG; VERY LATE ACTIVATION ANTIGEN 4;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYCLOADDITION; DRUG DESIGN; DRUG SYNTHESIS; ELIMINATION REACTION; HUMAN; HUMAN CELL; PRIORITY JOURNAL; X RAY ANALYSIS;

EID: 1942456710     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.03.025     Document Type: Article

References (49)

1. Sewald N., Jakubke H.-D. Peptides: chemistry and biology. 2002;Wiley-VCH, Weinheim. and references cited therein.
2. Giannis A., Kolter T. Angew. Chem. Int. Ed. 32:1993;1244-1267.
3. Hruby V.J. Life Sci. 31:1982;189-199.
4. Hruby V.J., Al-Obeidi F., Kazmierski W. Biochem. J. 268:1990;249-262.
5. Toniolo C., Benedetti E. Macromolecules. 24:1991;4004-4009.
6. Marshall G.R., Clarc J.D., Dunbar J.B. Jr., Smith G.D., Zabrocki J., Redlinski A.S., Leplawy M.T. Int. J. Pept. Protein Res. 32:1988;544-555.
7. Sewald N., Burger K. Synthesis of β-fluorine containing amino acids - synthesis and properties. Kukhar V.P., Soloshonok V.A. Fluorine containing amino acids - synthesis and properties. 1995;139-220 Wiley, Chichester.
8. Koksch B., Sewald N., Jakubke H.-D., Burger K. Synthesis and incorporation of α-trifluoromethyl substituted amino acids into peptides. Ojima I., Mc Carthy J.P., Welch J.T. Biomedical fronties of fluorine chemistry. ACS Symposium Series 639. 1996;42-58 ACS, Washington DC. and references cited therein.
9. Koksch B., Sewald N., Hofmann H.J., Burger K., Jakubke H.-D. J. Pept. Sci. 3:1997;157-167.
10. Renner C., Alefelder S., Bae J.H., Budisa N., Huber R., Moroder L. Angew. Chem. Int. Ed. 40:2001;923-925.
11. Tang Y., Ghirlanda G., Vaidehi N., Kua J., Mainz T.D., Goddard W.A. III, Degrado W.F., Tirrell D.A. Biochemistry. 40:2001;2790-2796.
12. Bilgicer B., Fichera A., Kumar K. J. Am. Chem. Soc. 123:2001;4393-4399.
13. Welch J.T. The effects of selective fluorination on reactivity in organic and bioorganic chemistry. Welch J.T. Selective fluorination in organic and bioorganic chemistry. ACS Symposium Series 456. 1991;1-15 ACS, Washington DC. and references cited therein.
14. Larsson U., Carlson R., Leroy J. Acta Chim. Scand. 47:1993;380-390.
15. Yoder C., Kumar K. Chem. Soc. Rev. 31:2002;335-341.
16. Souers A.J.M., Ellman J.A. Tetrahedron. 57:2001;7431-7448. and references cited therein.
17. Qiu W., Gu X., Soloshonok V.A., Carducci M.D., Hruby V.J. Tetrahedron Lett. 42:2001;145-148.
18. Wang W., Xiong C., Hruby V.J. Tetrahedron Lett. 42:2001;3159-3161.
19. Lopez C.A., Trigo G.G. Adv. Heterocycl. Chem. 38:1985;177.
20. Nefzi A., Ostresch J.M., Giulianotti M., Houghten R.A. Tetrahedron Lett. 39:1998;8199-8202.
21. Ganesan A., Sim M.M. J. Org. Chem. 62:1997;3230-3235.
22. Xiao X.-Y., Ngu K., Chao C., Patel D.V. J. Org. Chem. 62:1997;6968-6973.
23. Takeuchi Y., Kirihara K., Kirk K.L., Shibata N. J. Chem. Soc., Chem. Commun. 2000;785-786.
24. Zeifman Y.V., Gambaryan N.P., Knunyants I.L. Izvest. Acad. Nauk, SSSR, Ser. Khim. 1965;2046-2048. Chem. Abstr. 1966, 64, 6554f.
25. Steglich W., Burger K., Dürr M., Burgis E. Chem. Ber. 107:1974;1488-1498.
26. Burger K., Gaa K. Chem.-Ztg. 114:1990;101-104.
27. Osipov S.N., Chkanikov N.D., Kolomiets A.F., Fokin A.F. Izvest. Akad. Nauk, SSSR, Ser. Khim. 1986;1384-1387. Chem. Abstr. 1987, 106, 156213.
28. Burger K., Höß E., Gaa K., Sewald N., Schierlinger C. Z. Naturforsch. B. 46:1991;361-384.
29. Osipov S.N., Golubev A.S., Sewald N., Michel T., Kolomiets A.F., Fokin A.F., Burger K. J. Org. Chem. 61:1996;7521-7528.
30. Weygand F., Steglich W., Oettmeier W., Maierhofer A., Loy R.S. Angew. Chem. Int. Ed. 5:1966;600-601.
31. Gambaryan N.P., Rokhlin E.M., Zeifman Y.V., Simonyan I.A., Knunyants I.L. Dokl. Acad. Nauk. 166:1966;864-867. Chem. Abstr. 1966, 64, 15861.
32. Burger K., Wassmuth U., Penninger S. J. Fluorine Chem. 20:1983;813-825.
33. Burger K., Ottlinger R. Chem.-Ztg. 101:1977;402-403.
34. Fischer E.O., Weiss K., Burger K. Chem. Ber. 106:1973;1581-1588.
35. Burger K., Wucherpfennig U., Brunner E. Fluoro heterocycles with five-membered rings. Katritzky A.R. Advances in heterocyclic chemistry. Vol. 60:1994;1-64 Academic, London.
36. Burger K., Schierlinger C., Mütze K. J. Fluorine Chem. 65:1993;149-152.
37. Koksch B., Mütze K., Osipov S.N., Golubev A.S., Burger K. Tetrahedron Lett. 41:2000;3825-3828.
38. Hollweck W., Burger K. J. Prakt. Chem./Chem.-Ztg. 337:1995;391-396.
39. Mütze, K. PhD Thesis, TU Munich, 1993.
40. 13C NMR-spektroskopie. 1984;Georg Thieme, Stuttgart. pp 189-199.
41. 28 Further details on the structure are available on request from Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, UK on quoting depository number CCDC 217587.
42. Wehner, V.; Stilz, H. -U.; Burger, K.; Golubev, A.; Osipov, S. US patent. Pub. No.: US/0183374 2002 A1.
43. For a review see: Tietze L.F. Chem. Rev. 96:1996;115-136.
44. Burger K., Fuchs A., Hennig L., Helmreich B., Greif D. Monatsh. Chem. 132:2001;929-945.
45. Burger K., Fuchs A., Hennig L., Helmreich B. Tetrahedron Lett. 42:2001;1657-1659.
46. Burger K., Höβ E., Gaa K. Chem.-Ztg. 113:1989;243-247.
47. Deutsch J., Duczek W., Niclas H.-J. J. Prakt. Chem./Chem.-Ztg. 338:1996;488-490.
48. Duczek W., Deutsch J., Vieth S., Niclas H.-J. Synthesis. 1996;37-38.
49. Sheldrick,G. M. SHELX-97: A Program System for Solution and Refinement of X-ray Crystal Structures; University of Göttingen, 1997.