Synthesis and biological activity of β-fluoroalkyl β-amino alcohols

Journal of Fluorine Chemistry

Volumn 97, Issue 1-2, 1999, Pages 27-49

  Bravo, Pierfrancesco ^a   Crucianelli, Marcello ^b   Ono, Taizo ^c   Zanda, Matteo ^b,c  

^a CNR   (Italy)

^b POLITECNICO DI MILANO   (Italy)

^c NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

Amino alcohols; Bioactivity; Chiral; Florfenicol; Fluoroalkyl; Synthesis

Indexed keywords

EID: 0002563538     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(99)00024-X     Document Type: Review

References (89)

1. Cullis P.M., Lewendon A., Shaw W.V., Williams J.A. Biochem. 30:1991;3758.
2. T.L. Nagabhushan (Schering Corp.) (US patent no. 4235892, 1980) Chem. Abstr. 94 (1980) 139, 433.
3. Schumacher D.P., Clark J.E., Murphy B.L., Fischer P.A. J. Org. Chem. 55:1990;5291.
4. Takaoka A., Iwagiri H., Ishikawa N. Bull. Chem. Soc. Jpn. 52:1979;3377.
5. Giordano C., Cavicchioli S., Levi S., Villa M. J. Org. Chem. 56:1991;6114.
6. Wu G., Schumacher D.P., Tormos W., Clark J.E., Murphy B.L. J. Org. Chem. 62:1997;2996.
7. Katsuki T., Sharpless K.B. J. Am. Chem. Soc. 102:1980;5974.
8. Payne G.B. J. Org. Chem. 27:1962;3819.
9. J.E. Clark, P.A. Fischer, D.P. Schumacher, Synthesis (1991) 891.
10. R. Tyson, Chem. Ind. (1988) 118.
11. Jommi G., Pagliarin R., Chiarino D., Fantucci M. Gazz. Chim. Ital. 115:1985;653.
12. Sharts C.M., Sheppard W.A. Org. React. 21:1974;125.
13. Jommi G., Pagliarin R., Tavecchia P., Chiarino D., Fantucci M. Gazz. Chim. Ital. 116:1986;485.
14. Jommi G., Ripa A., Ripa G., Sisti M. Gazz. Chim. Ital. 118:1988;75.
15. G. Jommi, D. Chiarino, R. Pagliarin, US patent no. 4743700, 1988.
16. McCombie S.W., Nagabhushan T.L. Tetrahedron Lett. 28:1987;5395.
17. B. Lou, Y. Zhang, L. Dai, Chem. Ind. (1993) 249.
18. Tsushima T., Kawada K., Tsuji T., Tawara K. J. Med. Chem. 28:1985;253.
19. Wade T.N. J. Org. Chem. 45:1980;5328.
20. G.A. Olah, M. Nojima, I. Kerekes, Synthesis (1973) 779.
21. G. Camaggi, D. Chiarino, M. Fantucci, G. Meazza (Eur. patent appl. no. 454067) Chem. Abstr. 117 (1992) 48, 113.
22. Alvernhe G., Lacombe S., Laurent A. Tetrahedron Lett. 21:1980;1437.
23. G. Alvernhe, S. Lacombe, A. Laurent, C. Rousset, J. Chem. Res. (S) (1983) 246.
24. Fronza G., Fuganti C., Mele A., Pedrocchi Fantoni G. J. Carbohydr. Chem. 10:1991;197.
25. Devi N., Threadgill M.D., Tendler S.J.B. Synth. Commun. 18:1988;1545.
26. Kozikowski A.P., Wu J.-P. Tetrahedron Lett. 31:1990;4309.
27. Dax K., Graβberger V., Stütz A.E. J. Carbohydr. Chem. 9:1990;903.
28. Lee C.-K., Jiang H., Koh L.L., Xu Y. Carbohydr. Res. 239:1993;309.
29. Uno H., Okada S., Ono T., Shiraishi Y., Suzuki H. J. Org. Chem. 57:1992;1504.
30. J.B. Dickey, E.B. Towne (Eastman Kodak) (US patent no. 2700686), Chem. Abstr. 50 (1956) 5721e.
31. I.L. Knunyants, L.S. German, I.N. Rozhkov, Izv. Akad. Nauk SSSR, Ser. Khim. 9 (1964) 1630 [Chem. Abstr. 62 (1965) 430].
32. I.L. Knunyants, L.S. German, I.N. Rozhkov, Izv. Akad. Nauk SSSR, Ser. Khim. 9 (1964) 1630 [Chem. Abstr. 62 (1965) 430].
33. I.L. Knunyants, L.S. German, I.N. Rozhkov, Izv. Akad. Nauk SSSR, Ser. Khim. 9 (1964) 1630 [Chem. Abstr. 62 (1965) 430].
34. S.A. Konikov, I.M. Krilova, N.N. Shenberg, V.A. Gindin, L.F. Strelkova, V.V. Takhistov, A.N. Stukov, V.A. Filov, B.A. Ivin, Zh. Obshch. Khim. 64 (1994) 283 [Chem. Abstr. 121 (1994) 230, 315].
35. S.A. Konikov, I.M. Krilova, N.N. Shenberg, V.A. Gindin, L.F. Strelkova, V.V. Takhistov, A.N. Stukov, V.A. Filov, B.A. Ivin, Zh. Obshch. Khim. 64 (1994) 283 [Chem. Abstr. 121 (1994) 230, 315].
36. Li K., Leriche C., Liu H. Bioorg. Med. Chem. Lett. 8:1998;1097.
37. Quinze K., Laurent A., Mison P. J. Fluorine Chem. 44:1989;233.
38. de Raadt A., Ebner M., Ekhart C.W., Fechter M., Lechner A., Strobl M., Stütz A.E. Catalysis Today. 22:1994;549.
39. Berger A., Dax K., Gradnig G., Graβberger V., Stütz A.E., Ungerank M., Legler G., Bause E. Bioorg. Med. Chem. Lett. 2:1992;27.
40. Andersen S.M., Ebner M., Ekhart C.W., Gradnig G., Legler G., Lundt I., Stütz A.E., Withers S.G., Wrodnigg T. Carbohydr. Res. 301:1997;155.
41. Karimova N.M., Teplenicheva Yu.L., Kolomiets A.F., Fokin A.V. Russ. Chem. Bull. 46:1997;1136.
42. Katagiri T., Ihara H., Takahashi M., Kashino S., Furuhashi K., Uneyama K. Tetrahedron: Asym. 8:1997;2933.
43. Bravo P., Crucianelli M., Zanda M. Tetrahedron Lett. 36:1995;3043.
44. Arnone A., Bravo P., Bruché L., Crucianelli M., Vichi L., Zanda M. Tetrahedron Lett. 36:1995;7301.
45. A. Arnone, P. Bravo, S. Capelli, G. Fronza, S.V. Meille, M. Zanda, M. Crucianelli, G. Cavicchio, J. Org. Chem. 61 (1996) 3375 [Corrigenda 61 (1996) 9635].
46. A. Arnone, P. Bravo, S. Capelli, G. Fronza, S.V. Meille, M. Zanda, M. Crucianelli, G. Cavicchio, J. Org. Chem. 61 (1996) 3375 [Corrigenda 61 (1996) 9635].
47. Staudinger H., Meyer J. Helv. Chem. Acta. 2:1919;635.
48. P. Molina, M.J. Vilaplana, Synthesis (1994) 1197.
49. Pummerer R. Ber. Dtsch. Chem. Ges. 42:1909;2282.
50. O. de Lucchi, U. Miotti, G. Modena, in: L.A. Paquette (Ed.), Organic Reactions, Wiley, New York, vol. 40, 1991.
51. Bravo P., Cavicchio G., Crucianelli M., Poggiali A., Zanda M. Tetrahedron: Asym. 8:1997;2811.
52. O. Mitsunobu, Synthesis (1981) 1.
53. Shuto S., Ono S., Hase Y., Kamiyama N., Takada H., Yamasihita K., Matsuda A. J. Org. Chem. 61:1996;915.
54. Tanaka K., Ishiguro Y., Mitsuhashi K. Bull. Chem. Soc. Jpn. 66:1993;661.
55. Van Hijfte L., Heydt V., Kolb M. Tetrahedron Lett. 34:1993;4793.
56. Grob C.A., Schwartz W. Hel. Chim. Acta. 47:1964;1870.
57. Behr J.-B., Evina C.M., Phung N., Guillerm G. J. Chem. Soc. Perkin Trans. 1:1997;1597.
58. Todo Y., Takagi H., Iino F., Fukuoka Y., Takahata M., Okamoto S., Saikawa I., Narita H. Chem. Pharm. Bull. 42:1994;2569.
59. Baldwin J.E., Lynch G.P., Schofield C.J. Tetrahedron. 48:1992;9085.
60. Uneyama K., Hao J., Amii H. Tetrahedron Lett. 39:1998;4079.
61. A. Abouabdellah, J.-P. Bégué, D. Bonnet-Delpon, Synlett (1996) 399.
62. Abouabdellah A., Bégué J.-P., Bonnet-Delpon D., Thanh Nga T.T. J. Org. Chem. 62:1997;8826.
63. Ojima I., Slater J.C. Chirality. 9:1997;487.
64. Ojima I., Slater J.C., Pera P., Veith J.M., Abouabdellah A., Bégué J.-P., Bernacki R.J. Bioorg. Med. Chem. Lett. 7:1997;133.
65. Beck A.K., Seebach D. Chem. Ber. 124:1991;2897.
66. R.E. Marti, J. Heinzer, D. Seebach, Liebigs Ann. (1995) 1193.
67. P. Bravo, M. Zanda, in: V.A. Soloshonok (Ed.), Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemistry, Challenges and Biomedicinal Targets, Wiley, Chichester, in press.
68. Walker A.K. Tetrahedron: Asym. 3:1992;961.
69. Carreño M.C. Chem. Rev. 95:1995;1717.
70. Bravo P., Farina A., Kukhar V.P., Markovsky A.L., Meille S.V., Soloshonok V.A., Sorochinsky A.E., Viani F., Zanda M., Zappalá C. J. Org. Chem. 62:1997;3424.
71. Bravo P., Guidetti M., Viani F., Zanda M., Markovsky A.L., Sorochinsky A.E., Soloshonok I.V., Soloshonok V.A. Tetrahedron. 54:1998;12789.
72. S. Fustero, A. Navarro, B. Pina, P. Bravo, A. Volonterio, M. Zanda, to be published.
73. Bravo P., Corradi E., Pesenti C., Vergani B., Viani F., Volonterio A., Zanda M. Tetrahedron: Asym. 9:1998;3731.
74. Bravo P., Capelli S., Kukhar V.P., Meille S.V., Soloshonok V.A., Viani F., Zanda M. Tetrahedron: Asym. 5:1994;2009.
75. Bravo P., Zanda M., Zappalá C. Tetrahedron Lett. 37:1996;6005.
76. P. Bravo, M. Guidetti, A. Volonterio, M. Zanda, to be published.
77. Evans D.A., Bartroli J., Shih T.L. J. Am. Chem. Soc. 103:1981;2127.
78. Bravo P., Capelli S., Meille S.V., Seresini P., Volonterio A., Zanda M. Tetrahedron: Asym. 7:1996;2321.
79. S. Fustero, A. Navarro, A. Asensio, A. Volonterio, M. Zanda, to be published.
80. Fustero S., Navarro A., Pina B., Asensio A., Bravo P., Crucianelli M., Volonterio A., Zanda M. J. Org. Chem. 63:1998;6210.
81. P. Bravo, G. Cavicchio, M. Crucianelli, A.L. Markovsky, A. Volonterio, M. Zanda, Synlett (1996) 887.
82. P. Bravo, M. Crucianelli, A. Farina, S.V. Meille, A. Volonterio, M. Zanda, Eur. J. Org. Chem. (1998) 435.
83. Pictet A., Spengler T. Ber. Dtsch. Chem. Ges. 44:1911;2030.
84. Cox A.D., Cook J.M. Chem. Rev. 95:1995;1797.
85. P. Bravo, M. Crucianelli, G. Fronza, M. Zanda, Synlett (1996) 249.
86. Volonterio A., Zanda M., Bravo P., Fronza G., Cavicchio G., Crucianelli M. J. Org. Chem. 62:1997;8031.
87. Bjørsvik H.-R., Bravo P., Crucianelli M., Volonterio A., Zanda M. Tetrahedron: Asym. 8:1997;2817.
88. Volonterio A., Bravo P., Capelli S., Meille S.V., Zanda M. Tetrahedron Lett. 38:1997;1847.
89. Volonterio A., Vergani B., Crucianelli M., Zanda M., Bravo P. J. Org. Chem. 63:1998;7236.