Synthesis of aminopyrimidylindoles structurally related to meridianins

Tetrahedron

Volumn 63, Issue 41, 2007, Pages 10169-10176

  Rossignol, Emilie ^a   Youssef, Ali ^a   Moreau, Pascale ^a   Prudhomme, Michelle ^a   Anizon, Fabrice ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

Antitumor agents; Indole; Kinase inhibitors; Meridianins; Pyrimidine

Indexed keywords

1 METHYL 3 (3 N,N DIMETHYLAMINO 1 OXOPROP 2 ENYL) 1H INDOLE; 3 (2 AMINO 5 (4 TRIFLUOROMETHOXYPHENYL)PYRIMIDIN 4 YL] 1H INDOLE; 3 (2 AMINO 5 BROMOPYRIMIDIN 4 YL) 1 METHYL 1H INDOLE; 3 (2 AMINO 5 BROMOPYRIMIDIN 4 YL) 1H INDOLE; 3 (2 AMINO 5 PHENYLPYRIMIDIN 4 YL) 1 METHYL 1H INDOLE; 3 (2 AMINO 5 PHENYLPYRIMIDIN 4 YL) 1H INDOL; 3 (2 AMINOPYRIMIDIN 4 YL) 1H INDOLE; 3 (3 N,N DIMETHYLAMINO 1 OXOPROP 2 ENYL) 1H INDOLE; 3 [2 AMINO 5 (2,4 DIFLUOROPHENYL)PYRIMIDIN 4 YL] 1 METHYL 1H INDOLE; 3 [2 AMINO 5 (2,4 DIFLUOROPHENYL)PYRIMIDIN 4 YL] 1H INDOLE; 3 [2 AMINO 5 (4 ACETYLPHENYL)PYRIMIDIN 4 YL] 1 METHYL 1H INDOLE; 3 [2 AMINO 5 (4 ACETYLPHENYL)PYRIMIDIN 4 YL] 1H INDOLE; 3 [2 AMINO 5 (4 BIPHENYL)PYRIMIDIN 4 YL) 1H INDOLE; 3 [2 AMINO 5 (4 BIPHENYL)PYRIMIDIN 4 YL] 1 METHYL 1H INDOLE; 3 [2 AMINO 5 (4 FLUOROPHENYL)PYRIMIDIN 4 YL] 1 METHYL 1HINDOLE; 3 [2 AMINO 5 (4 FLUOROPHENYL)PYRIMIDIN 4 YL] 1H INDOLE; 3 [2 AMINO 5 (4 TRIFLUOROMETHOXYPHENYL)PYRIMIDIN 4 YL 1 METHYL 1H INDOLE; 3 [2 AMINO 5 (4 TRIFLUOROMETHYLPHENYL)PYRIMIDIN 4 YL] 1 METHYL 1H INDOLE; 3 [2 AMINO 5 (4 TRIFLUOROMETHYLPHENYL)PYRIMIDIN 4 YL] 1H INDOLE; INDOLE ALKALOID; INDOLE DERIVATIVE; MERIDIANIN; METHYL GROUP; NITROGEN; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; AMINO ACID SYNTHESIS; ARTICLE; BROMINATION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; SUZUKI REACTION;

EID: 34548247722     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.095     Document Type: Article

References (66)

1. Jiang X., Zhao B., Britton R., Lim L.Y., Leong D., Sanghera J.S., Zhou B.-B.S., Piers E., Andersen R.J., and Roberge M. Mol. Cancer Ther. 3 (2004) 1221
2. Hénon H., Messaoudi S., Anizon F., Aboab B., Kucharczyk N., Léonce S., Golsteyn R.M., Pfeiffer B., and Prudhomme M. Eur. J. Pharmacol. 554 (2007) 106
3. Meijer L., and Raymond E. Acc. Chem. Res. 36 (2003) 417
4. Eisenbrand G., Hippe F., Jakobs S., and Muehlbeyer S. J. Cancer Res. Clin. Oncol. 130 (2004) 627
5. Sassatelli M., Bouchikhi F., Messaoudi S., Anizon F., Debiton E., Barthomeuf C., Prudhomme M., and Moreau P. Eur. J. Med. Chem. 41 (2006) 88
6. Tamaoki T., Nomoto H., Takahashi I., Kato Y., Morimoto M., and Tomita F. Biochem. Biophys. Res. Commun. 135 (1986) 397
7. Omura S., Sasaki Y., Iwai Y., and Takeshima H. J. Antibiot. 48 (1995) 535
8. Mizuno K., Saido T.C., Ohno S., Tamaoki T., and Suzuki K. FEBS Lett. 330 (1993) 114
9. Nakanishi S., Matsuda Y., Iwahashi K., and Kase H. J. Antibiot. 34 (1986) 1066
10. Toullec D., Pianetti P., Coste H., Bellevergue P., Grand-Perret T., Ajakane M., Baudet V., Boissin P., Boursier E., Loriolle F., Duhamel L., Charon D., and Kirilovsky J. J. Biol. Chem. 266 (1991) 15771
11. Davis P.D., Hill C.H., Keech E., Lawton G., Nixon J.S., Sedgwick A.D., Wadsworth J., Westmacott D., and Wilkinson S.E. FEBS Lett. 259 (1989) 61
12. Davis, P. D.; Hill, C. H.; Lawton, G. Eur. Patent EP0328026 A1, 1989;
13. Chem. Abstr. 112 (1990) 98378
14. Franco L.H., Bal de Kier Joffé E., Puricelli L., Tatian M., Seldes A.M., and Palermo J.A. J. Nat. Prod. 61 (1998) 1130
15. Franco L.H., and Palermo J.A. Chem. Pharm. Bull. 51 (2003) 975
16. Gompel M., Leost M., Bal de Kier Joffé E., Puricelli L., Franco L.H., Palermo J., and Meijer L. Bioorg. Med. Chem. Lett. 14 (2004) 1703
17. Radwan M.A.A., and El-Sherbiny M. Bioorg. Med. Chem. 14 (2007) 1206
18. Huang S., Li R., Connolly P.J., Emanuel S., Fuentes-Pesquera A., Adams M., Gruninger R.H., Seraj J., Middleton S.A., Davis J.M., and Moffat D.F.C. Bioorg. Med. Chem. Lett. 17 (2007) 2179
19. Fischer, P. M.; Wang, S.; Meades, C. K.; Andrews, M. J. I.; Gibson, D.; Duncan, K. PCT Int. Appl. WO 2006075152 A1, 2006;
20. Chem. Abstr. 145 (2006) 167275
21. Ratcliffe, A. J.; Alam, M.; Beevers, R. E.; Davenport, R. J.; Davies, N.; Haughan, A. F.; Jones, M. W.; Lowe, C.; Perry, B. G.; Phillips, D. J.; Pitt, W. R.; Sharpe, A. PCT Int. Appl. WO 2006038001 A1, 2006;
22. Chem. Abstr. 144 (2006) 390934
23. Bressi, J. C.; Gangloff, A. R.; Hosfield, D. J.; Jennings, A. J.; Paraselli, B. R.; Stafford, J. A. PCT Int. Appl. WO 2005123672 A2, 2005;
24. Chem. Abstr. 144 (2006) 88168
25. Reddy, E. P.; Reddy, M. V. R.; Cosenza, S. C.; Gumireddy, K. PCT Int. Appl. WO 2005065074 A2, 2005;
26. Chem. Abstr. 143 (2005) 149136
27. Agarwal A., Srivastava K., Puri S.K., and Chauhan P.M.S. Bioorg. Med. Chem. Lett. 15 (2005) 3133
28. Agarwal A., Kumar B., Mehrotra P.K., and Chauhan P.M.S. Bioorg. Med. Chem. 13 (2005) 1893
29. Bollbuck, B.; Denholm, A.; Eder, J.; Hersperger, R.; Janser, P.; Revesz, L.; Schlapbach, A.; Waelchli, R. PCT Int. Appl. WO 2004089913 A1, 2004;
30. Chem. Abstr. 141 (2004) 379931
31. Kidwai M., Rastogi S., and Saxena S. Bull. Korean Chem. Soc. 24 (2003) 1575
32. Kim, Y.; Hanney, B. PCT Int. Appl. WO 2002102783, 2002;
33. Chem. Abstr. 138 (2003) 55974
34. Batchelor, M. J.; Moffat, D. F. C.; Davis, J. M.; Hutchings, M. C. PCT Int. Appl. WO 2000078731 A1, 2000;
35. Chem. Abstr. 134 (2001) 71598
36. Berger, J.; Flippin, L. A.; Greenhouse, R.; Jaime-Figueroa, S.; Liu, Y.; Miller, A. K.; Putman, D. G.; Weinhardt, K. K.; Zhao, S.-H. PCT Int. Appl. WO 9744326 A1, 1997;
37. Chem. Abstr. 128 (1998) 48235
38. Davis, P. D.; Moffat, D. F. C.; Davis, J. M.; Hutchings, M. C. PCT Int. Appl. WO 9719065 A1, 1997;
39. Chem. Abstr. 127 (1997) 81461
40. Zimmerman J., Buchdunger E., Mett H., Meyer T., and Lydon N.B. Bioorg. Med. Chem. Lett. 7 (1997) 187
41. Zimmerman J., Caravatti G., Mett H., Meyer T., Mueller M., Lydon N.B., and Fabbro D. Arch. Pharm. (Weinheim, Ger.) 329 (1996) 371
42. Zimmerman, J. PCT Int. Appl. WO 9509847 A1, 1995;
43. Chem. Abstr. 123 (1995) 313996
44. Zimmerman, J. PCT Int. Appl. WO 9509852 A1, 1995;
45. Chem. Abstr. 123 (1995) 169650
46. Paul R., Hallett W.A., Hanifin J.W., Reich M.F., Johnson B.D., Lenhard R.H., Dusza J.P., Kerwar S.S., Lin Y.-I., Pickett W.C., Seifert C.M., Torley L.W., Tarrant M.E., and Wrenn S. J. Med. Chem. 36 (1993) 2716
47. Torley, L. W.; Johnson, B. B.; Dusza, J. P. Eur. Pat. Appl. EP 233461 A2, 1987;
48. Chem. Abstr. 108 (1988) 112478
49. Kobayashi, G.; Matsuda, Y. Jpn Tokyo Koho JP 46008698, 1971;
50. Chem. Abstr. 75 (1971) 449129
51. Kobayashi G., Furukawa S., Matsuda Y., and Washida Y. Yakugaku Zasshi 87 (1967) 857
52. Davies S.P., Reddy H., Caivano M., and Cohen P. Biochem. J. 351 (2000) 95
53. Bain J., McLauchlan H., Elliott M., and Cohen P. Biochem. J. 371 (2003) 199
54. http://www.upstate.com/features/kp_reference.asp.
55. Peifer C., Stoiber T., Unger E., Totzke F., Schächtele C., Marmé D., Brenk R., Klebe G., Schollmeyer D., and Dannhardt G. J. Med. Chem. 49 (2006) 1271
56. Dow R.L. Curr. Med. Chem. 1 (1994) 192
57. Jiang B., and Yang C.-G. Heterocycles 53 (2000) 1489
58. Fresneda P.M., Molina P., Delgado S., and Bleda J.A. Tetrahedron Lett. 41 (2000) 4777
59. Fresneda P.M., Molina P., and Bleda J.A. Tetrahedron 57 (2001) 2355
60. Karpov A.S., Merkul E., Rominger F., and Müller T.J.J. Angew. Chem., Int. Ed. 44 (2005) 6951
61. Fresneda P.M., Delgado S., Francesch A., Manzanares I., Cuevas C., and Molina P. J. Med. Chem. 49 (2006) 1217
62. Bergman J., and Rehn S. Tetrahedron 58 (2002) 9179
63. Stanovnik B., and Svete J. Chem. Rev. 104 (2004) 2433
64. Meissner A., and Sørensen W. Magn. Reson. Chem. 39 (2001) 49
65. Byth K.F., Culshaw J.D., Green S., Oakes S.E., and Thomas A.P. Bioorg. Med. Chem. Lett. 14 (2004) 2245
66. Hannah D.R., Sherer E.C., Davies R.V., Titman R.B., Laughton C.A., and Stevens M.F.G. Bioorg. Med. Chem. 8 (2000) 739