Synthetic studies of 3-(3-fluorooxindol-3-yl)-l-alanine

Journal of Fluorine Chemistry

Volumn 129, Issue 9, 2008, Pages 829-835

  Fujiwara, Tomoya ^a   Yin, Bin ^a   Jin, Meixiang ^a   Kirk, Kenneth L ^b   Takeuchi, Yoshio ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

Epimerization; Fluorooxindole; Hydroxyoxindole; Indole; Oxindole; Oxindolylalanine; Selectfluor ; Tryptophan

Indexed keywords

EID: 50849121054     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.06.026     Document Type: Article

References (39)

1. Ma J., and Hecht S.M. Chem. Commun. (2004) 1190-1191
2. Kam T., and Choo Y. Phytochemistry 65 (2004) 603-608
3. Pandey R., Singh S.C., and Gupta M.M. Phytochemistry 67 (2006) 2164-2169
4. Kogure N., Ishii N., Kitajima M., Wongseripipatana S., and Takayama H. Org. Lett. 8 (2006) 3085-3088
5. Kagata T., Saito S., Shigemori H., Ohsaki A., Ishiyama H., Kubota T., and Kobayashi J. J. Nat. Prod. 69 (2006) 1517-1521
6. Suzuki H., Morita H., Shiro M., and Kobayashi J. Tetrahedron 60 (2004) 2489-2495
7. Dermatakis A., Luk K., and DePinto W. Bioorg. Med. Chem. Lett. 13 (2003) 1873-1881
8. Natarajan A., Fan Y., Chen H., Guo Y., Iyasere J., Harbinski F., Christ W.J., Aktas H., and Halperin J.A. J. Med. Chem. 47 (2004) 1882-1885
9. Pandit B., Sun Y., Chen P., Sackett D.L., Hu Z., Rich W., Li C., Lewis A., Schaefera K., and Lia P. Bioorg. Med. Chem. 14 (2006) 6492-6501
10. Li H., Zhang X., Tan J., Chen L., Liu H., Luo X., Shen X., Lin L., Chen K., Ding J., and Jiang H. Acta Pharmacol. Sin. 28 (2007) 140-152
11. Tokunaga T., Hume W.E., Umezome T., Okazaki K., Ueki Y., Kumagai K., Hourai S., Nagamine J., Seki H., Taiji M., Noguchi H., and Nagata R. J. Med. Chem. 44 (2001) 4641-4649
12. Tokunaga T., Hume W.E., Nagamine J., Kawamura T., Taiji M., and Nagata R. Bioorg. Med. Chem. Lett. 15 (2005) 1789-1792
13. Koguchi Y., Kohno J., Nishio M., Takahashi K., Okuda T., Ohnuki T., and Komatsubara S. J. Antibiot. 53 (2000) 105-109
14. Kohno J., Koguchi Y., Nishio M., Nakao K., Kuroda M., Shimizu R., Ohnuki T., and Komatsubara S. J. Org. Chem. 65 (2000) 990-995
15. Borissenko L., and Groll M. Chem. Rev. 107 (2007) 687-717
16. Phillips R.S., Miles E.W., and Cohen L.A. Biochemistry 23 (1984) 6228-6234
17. Phillips R.S., Miles E.W., and Cohen L.A. J. Biol. Chem. 260 (1985) 14665-14670
18. Kiick D.M., and Phillips R.S. Biochemistry 27 (1988) 7339-7344
19. Roy M., Miles E.W., Phillips R.S., and Dunn M.F. Biochemistry 27 (1988) 8661-8669
20. Phillips R.S., Bender S.L., Brzovic P., and Dunn M.F. Biochemistry 29 (1990) 8608-8614
21. Labroo R.B., and Cohen L.A. J. Org. Chem. 55 (1990) 4901-4904
22. Takeuchi Y., Shiragami T., Kimura K., Suzuki E., and Shibata N. Org. Lett. 1 (1999) 1571-1573
23. Chem. Abstr., 136, 247496v (2002).
24. Y. Takeuchi, N. Shibata, E. Suzuki, Y. Iimura, T. Kosasa, T. Yamanishi, H. Sugimoto, PCT Int. Appl. WO 2002020482.
25. Fujisawa H., Fujiwara T., Takeuchi Y., and Omata K. Chem. Pharm. Bull. 53 (2005) 524-528
26. Takeuchi Y., Fujisawa H., Fujiwara T., Matsuura M., Komatsu H., Ueno S., and Matsuzaki T. Chem. Pharm. Bull. 53 (2005) 1062-1064
27. Ojima I., McCarthy J.R., and Welch J.T. Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639 (1996), American Chemical Society, Washington, DC
28. Filler R., and Kobayashi Y. Biomedical Aspects of Fluorine Chemistry (1982), Kodansha/Elsevier Biomedical, Tokyo
29. Blaschke G., Kraft H.P., Fickentscher K., and Koehler F. Arzneim. -Forsch./Drug Res. 29 (1979) 1640-1642
30. Nishimura K., Hashimoto Y., and Iwasaki S. Biochem. Biophys. Res. Commun. 199 (1994) 455-460
31. Winter W., and Frankus E. Lancet 339 (1992) 365
32. Xu Y., Qian L., and Prestwich G.D. J. Org. Chem. 68 (2003) 5320-5330
33. Jäckel C., and Koksch B. Eur. J. Org. Chem. (2005) 4483-4503
34. Hewawasam P., Gribkoff V.K., Pendri Y., Dworetzky S.I., Meanwell N.A., Martinez E., Boissard C.G., Post-Munson D.J., Trojnacki J.T., Yeleswaram K., Pajor L.M., Knipe J., Gao Q., Perrone R., and Starrett Jr. J.E. Bioorg. Med. Chem. Lett. 12 (2002) 1023-1026
35. Takeuchi Y., Tarui T., and Shibata N. Org. Lett. 2 (2000) 639-642
36. Banks R.E. J. Fluorine Chem. 87 (1998) 1-17
37. Lal G.S., Pez G.P., and Syvret R.G. Chem. Rev. 96 (1996) 1737-1755
38. Taniguchi M., and Hino T. Tetrahedron 37 (1981) 1487-1494
39. Kiso Y., Inai M., Kitagawa K., and Akita T. Chem. Lett. (1983) 739-742