1.5 Fluorine in Medicinal Chemistry: Importance of Chirality

Comprehensive Chirality

Volumn 1, Issue , 2012, Pages 70-85

  Tredwell, M ^a   Gouverneur, V ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Amide isosteres; Camptothecin; Conformational effects; Efavirenz; Fluorinated nucleosides; Fluorinated steroids; Indinavir; Lipophilicity; MaxiPost; Stereoelectronic effects; Steric size; Thalidomide

Indexed keywords

EID: 84897384985     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-08-095167-6.00106-3     Document Type: Chapter

References (81)

1. Jeschke P. ChemBioChem 2004, 5(5):570-589.
2. Hagmann W.K. J. Med. Chem. 2008, 51(15):4359-4369.
3. O'Hagan D. J. Fluorine Chem. 2010, 131(11):1071-1081.
4. Harper D.B., O'Hagan D. Nat. Pro. Rep. 1994, 11:123-133.
5. O'Hagan D., Harper D.B. J. Fluorine Chem. 1999, 100(1-2):127-133.
6. Smart B.E. J. Fluorine Chem. 2001, 109(1):3-11.
7. Lemal D.M. J. Org. Chem. 2004, 69(1):1-11.
8. Böhm H.-J., Banner D., Bendels S., et al. ChemBioChem 2004, 5(5):637-643.
9. Müller K., Faeh C., Diederich F. Science 2007, 317(5846):1881-1886.
10. O'Hagan D. Chem. Soc. Rev. 2008, 37:308-319.
11. Purser S., Moore P.R., Swallow S., Gouverneur V. Chem. Soc. Rev. 2008, 37:320-330.
12. Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications 2004, Wiley-VCH, Weinheim.
13. Uneyama K. Organofluorine Chemistry 2006, Blackwell, Oxford.
14. Bégué J.-P., Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine 2007, Wiley, Hoboken.
15. Smart B.E. Molecular Structure and Energetics 1986, Vol. 3:141-191. VCH Publishers, Deerfield Beach, Chapter 4.
16. Blanksby S.J., Ellison G.B. Acc. Chem. Res. 2003, 36(4):255-263.
17. Pauling L. The Nature of the Chemical Bond and the Structure of Molecules and Crystals: An Introduction to Modern Structural Chemistry 1939, Cornell University Press, Ithaca.
18. van Niel M.B., Collins I., Beer M.S., et al. J. Med. Chem. 1999, 42(12):2087-2104.
19. Blint R.J., McMahon T.B., Beauchamp J.L. J. Am. Chem. Soc. 1974, 96(5):1269-1278.
20. Rowley M., Hallett D.J., Goodacre S. J. Med. Chem. 2001, 44(10):1603-1614.
21. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. Adv. Drug Deliv. Rev. 2001, 46(1-3):3-26.
22. Hansch C., Maloney P.P., Fujita T., Muir R.M. Nature 1962, 194(4824):178-180.
23. Fujita T., Iwasa J., Hansch C. J. Am. Chem. Soc. 1964, 86(23):5175-5180.
24. Leo A., Hansch C., Elkins D. Chem. Rev. 1971, 71(6):525-616.
25. Hansch C., Leo A., Unger S.H., et al. J. Med. Chem. 1973, 16(11):1207-1216.
26. Bondi A. J. Phys. Chem. 1964, 68(3):441-451.
27. Eliel E.L., Wilen S.H., Mander L.N. Stereochemistry of Organic Compounds 1994, Wiley, New York.
28. Taft J.R.W. Steric Effects in Organic Chemistry 1956, Wiley, New York.
29. Tvaroska I., Carver J.P. J. Phys. Chem. 1994, 98(26):6452-6458.
30. Takahashi O., Yamasaki K., et al. Carbohydr. Res. 2009, 344(10):1225-1229.
31. Wolfe S. Acc. Chem. Res. 1972, 5(3):102-111.
32. Thibaudeau C., Plavec J., Garg N., et al. J. Am. Chem. Soc. 1994, 116(9):4038-4043.
33. Wiberg K.B., Murcko M.A., Laidig K.E., MacDougall P.J. J. Phys. Chem. 1990, 94(18):6956-6959.
34. O'Hagan D., Bilton C., Howard J.A.K., Knight L., Tozer D.J. J. Chem. Soc. Perkin Trans. 2 2000, (4):605-607.
35. Briggs C.R.S., Allen M.J., O'Hagan D., et al. Org. Biomol. Chem. 2004, 2(5):732-740.
36. Sum A., Lankin D.C., Hardcastle K., Snyder J.P. Chem. - Eur. J. 2005, 11(5):1579-1591.
37. Howard J.A.K., Hoy V.J., O'Hagan D., Smith G.T. Tetrahedron 1996, 52(38):12613-12622.
38. Dunitz J.D., Taylor R. Chem. - Eur. J. 1997, 3(1):89-98.
39. Dunitz J.D. ChemBioChem 2004, 5(5):614-621.
40. Cantacuzene D., Kirk K.L., McCulloh D.H., Creveling C.R. Science 1979, 204(4398):1217-1219.
41. Fried J., Sabo E.F. J. Am. Chem. Soc. 1954, 76(5):1455-1456.
42. Phillipps G.H., Bailey E.J., Bain B.M., et al. J. Med. Chem. 1994, 37(22):3717-3729.
43. Banks R.E. J. Fluorine Chem. 1998, 87(1):1-17.
44. Chernyak, S.; Zarbov, M.; Gutman, D. (Taro Pharmaceuticals U.S.A. Inc) Method for the Preparation of 6-α Fluoro Corticosteroids. US Patent 7,718,793 B2, May 18th 2010.
45. Waller C.W., Patrick J.B., Fulmor W., Meyer W.E. J. Am. Chem. Soc. 1957, 79(4):1011-1012.
46. Pankiewicz K.W. Carbohydr. Res. 2000, 327(1-2):87-105.
47. Tann C.H., Brodfuehrer P.R., Brundidge S.P., Sapino C., Howell H.G. J. Org. Chem. 1985, 50(19):3644-3647.
48. Bauta W.E., Schulmeier B.E., Burke B. Org. Process Res. Dev. 2004, 8(6):889-896.
49. Pankiewicz K.W., Krzeminski J., Ciszewski L.A., Ren W.-Y., Watanabe K.A. J. Org. Chem. 1992, 57(2):553-559.
50. Pankiewicz K.W., Krzeminski J., Watanabe K.A. J. Org. Chem. 1992, 57(26):7315-7321.
51. Brik A., Wong C.-H. Org. Biomol. Chem. 2003, 1(1):5-14.
52. Myers A.G., Barbay J.K., Zhong B. J. Am. Chem. Soc. 2001, 123(30):7207-7219.
53. Wall M.E., Wani M.C., Cook C.E., et al. J. Am. Chem. Soc. 1966, 88(16):3888-3890.
54. Lavergne O., Demarquay D., Bailly C., et al. J. Med. Chem. 2000, 43(11):2285-2289.
55. Staker B.L., Hjerrild K., Feese M.D., et al. Proc. Natl. Acad. Sci. USA 2002, 99(24):15387-15392.
56. Tangirala R.S., Dixon R., Yang D., et al. Bioorg. Med. Chem. Lett. 2005, 15(21):4736-4740.
57. Shibata N., Ishimaru T., Nakamura M., Toru T. Synlett 2004, 14:2509-2512.
58. Shibata N., Suzuki E., Asahi T., Shiro M. J. Am. Chem. Soc. 2001, 123(29):7001-7009.
59. Mohar B., Baudoux J., Plaquevent J.-C., Cahard D. Angew. Chem., Int. Ed. 2001, 40(22):4214-4216.
60. Ishimaru T., Shibata N., Horikawa T., et al. Angew. Chem., Int. Ed. 2008, 47(22):4157-4161.
61. Hewawasam P., Gribkoff V.K., Pendri Y., et al. Bioorg. Med. Chem. Lett. 2002, 12(7):1023-1026.
62. Shibata N., Ishimaru T., Suzuki E., Kirk K.L. J. Org. Chem. 2003, 68(6):2494-2497.
63. Zoute L., Audouard C., Plaquevent J.-C., Cahard D. Org. Biomol. Chem. 2003, 1(11):1833-1834.
64. Shibata N., Ishimaru T., Nagai T., Kohno J., Toru T. Synlett 2004, 10:1703-1706.
65. Shibata N., Kohno J., Takai K., et al. Angew. Chem., Int. Ed. 2005, 44(27):4204-4207.
66. Hamashima Y., Yagi K., Takano H., Tamás L., Sodeoka M. J. Am. Chem. Soc. 2002, 124(49):14530-14531.
67. Hamashima Y., Suzuki T., Takano H., Shimura Y., Sodeoka M. J. Am. Chem. Soc. 2005, 127(29):10164-10165.
68. Sheskin J. Clin. Pharmacol. Ther. 1965, 6(3):303-306.
69. Sampaio E.P., Sarno E.N., Galilly R., Cohn Z.A., Kaplan G. J. Exp. Med. 1991, 173(3):699-703.
70. Eriksson T., Bjöurkman S., Roth B., Fyge Å., Höuglund P. Chirality 1995, 7(1):44-52.
71. Takeuchi Y., Shiragami T., Kimura K., Suzuki E., Shibata N. Org. Lett. 1999, 1(10):1571-1573.
72. Man H.-W., Corral L.G., Stirling D.I., Muller G.W. Bioorg. Med. Chem. Lett. 2003, 13(20):3415-3417.
73. Mei Y., He X., Xiang Y., Zhang D.W., Zhang J.Z.H. Proteins 2005, 59(3):489-495.
74. Pierce M.E., Parsons R.L., Radesca L.A., et al. J. Org. Chem. 1998, 63(23):8536-8543.
75. Tan L., Chen C.-Y., Tillyer R.D., Grabowski E.J.J., Reider P.J. Angew. Chem., Int. Ed. 1999, 38(5):711-713.
76. Sani M., Volonterio A., Zanda M. ChemMedChem 2007, 2(12):1693-1700.
77. Volonterio A., Bellosta S., Bravo P., et al. Eur. J. Org. Chem. 2002, 3:428-438.
78. Molteni M., Volonterio A., Zanda M. Org. Lett. 2003, 5(21):3887-3890.
79. Black W.C., Bayly C.I., Davis D.E., et al. Bioorg. Med. Chem. Lett. 2005, 15(21):4741-4744.
80. Li C.S., Deschenes D., Desmarais S., Falgueyret J.-P., et al. Bioorg. Med. Chem. Lett. 2006, 16(7):1985-1989.
81. Hughes G., Devine P.N., Naber J.R., et al. Angew. Chem., Int. Ed. 2007, 46(11):1839-1842.