Synthesis of a novel macrocyclic library: Discovery of an IGF-1R inhibitor

Journal of Combinatorial Chemistry

Volumn 10, Issue 2, 2008, Pages 256-266

  Qvit, Nir ^a   Reuveni, Hadas ^a   Gazal, Sharon ^a   Zundelevich, Adi ^a   Blum, Galia ^a,b   Niv, Masha Y ^a   Feldstein, Alexandra ^a   Meushar, Sharon ^a   Shalev, Deborah E ^a   Friedler, Assaf ^a   Gilon, Chaim ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b STANFORD UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; SOMATOMEDIN C RECEPTOR;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; RECEPTOR, IGF TYPE 1;

EID: 42449085846     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc700113c     Document Type: Article

References (53)

1. Schreiber, S. L. Science 2000, 287, 1964-1969.
2. Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251.
3. Hall, D. G.; Manku, S.; Wang, F. J. Comb. Chem. 2001, 3, 125-150.
4. Haskell-Luevano, C.; Rosenquist, A.; Souers, A.; Khong, K. C.; Ellman, J. A.; Cone, R. D. J. Med. Chem. 1999, 42, 4380-4387.
5. Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448.
6. Bondebjerg, J.; Xiang, Z. M.; Bauzo, R. M.; Haskell-Luevano, C.; Meldal, M. J. Am. Chem. Soc. 2002, 124, 11046-11055.
7. Reichwein, J. F.; Versluis, C.; Liskamp, R. M. J. Org. Chem. 2000, 65, 6187-6195.
8. Brouwer, A. J.; Liskamp, R. M. J. Org. Chem. 2004, 69, 3662-3668.
9. Karush, F. J. Am. Chem. Soc. 1950, 72, 2705-2713.
10. Pauling, L. J. Am. Chem. Soc. 1940, 62, 2643-2657.
11. Arkin, M. R.; Wells, J. A. Nat. Rev. Drug Discovery 2004, 3, 301-317.
12. Zhao, L.; Chmielewski, J. Curr. Opin. Struct. Biol. 2005, 15, 31-34.
13. Sillerud, L. O.; Larson, R. S. Curr. Protein Pept. Sci. 2005, 6, 151-169.
14. Levitzki, A.; Mishani, E. Annu. Rev. Biochem. 2006, 75, 93-109.
15. Ludesche, U.; Schwyzer, R. Helv. Chim. Acta 1971, 54, 1637-1644.
16. Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204-12205.
17. Cheng, M. F.; Fang, J. M. J. Comb. Chem. 2004, 6, 99-104.
18. Blum, G.; Gazit, A.; Levitzki, A. J. Biol. Chem. 2003, 278, 40442-40454.
19. Favelyukis, S.; Till, J. H.; Hubbard, S. R.; Miller, W. T. Nat. Struct. Biol. 2001, 8, 1058-1063.
20. Bohula, E. A.; Playford, M. P.; Macaulay, V. M. Anticancer Drugs 2003, 14, 669-682.
21. Djavan, B.; Waldert, M.; Seitz, C.; Marberger, M. World J. Urol. 2001, 19, 225-233.
22. Pollak, M. N.; Schernhammer, E. S.; Hankinson, S. E. Nat. Rev. Cancer 2004, 4, 505-518.
23. Resnicoff, M.; Abraham, D.; Yutanawiboonchai, W.; Rotman, H. L.; Kajstura, J.; Rubin, R.; Zoltick, P.; Baserga, R. Cancer Res. 1995, 55, 2463-2469.
24. Dunn, S. E.; Ehrlich, M.; Sharp, N. J.; Reiss, K.; Solomon, G.; Hawkins, R.; Baserga, R.; Barrett, J. C. Cancer Res. 1998, 58, 3353-3361.
25. Riedemann, J.; Macaulay, V. M. Endocr. Relat. Cancer 2006, 13, S33-43.
26. Lipinski, C. A. J. Pharmacol. Toxicol. Methods 2000, 44, 235-249.
27. Veber, D. F.; Johnson, S. R.; Cheng, H. Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. J. Med. Chem. 2002, 45, 2615-2623.
28. Gazal, S.; Gellerman, G.; Glukhov, E.; Gilon, C. J. Pept. Res. 2001, 58, 527-539.
29. Otaka, A.; Koide, T.; Shide, A.; Fujii, N. Tetrahedron Lett. 1991, 32, 1223-1226.
30. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
31. Houghten, R. A. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 5131-5135.
32. Falb, E.; Yechezkel, T.; Salitra, Y.; Gilon, C. J. Pept. Res. 1999, 53, 507-517.
33. Rose, J. D.; Parker, W. B.; Someya, H.; Shaddix, S. C.; Montgomery, J. A.; Secrist, J. A. J. Med. Chem. 2002, 45, 4505-4512.
34. Fridkin, G.; Gilon, C.; Gilon, T.; Loyter, A. J. Pept. Res. 2001, 58, 36-44.
35. Carrington, S.; Renault, J.; Tomasi, S.; Corbel, J. C.; Uriac, P.; Blagbrough, I. S. Chem. Commun. 1999, 1341-1342.
36. Khan, N. M.; Arumugam, V.; Balasubramanian, S. Tetrahedron Lett. 1996, 37, 4819-4822.
37. Kung, P.; Swayze, E. Tetrahedron Lett. 1999, 40, 5651-5654.
38. Jefferson, E. A.; Swayze, E. Tetrahedron Lett. 1999, 40, 7757-7760.
39. Sidorova, M. V.; Molokoedov, A. S.; Az'muko, A. A.; Kudryavtseva, E. V.; Krause, E.; Ovchinnikov, M. V.; Bespalova, Z. D. Russ. J. Bioorg. Chem. 2004, 30, 101-110.
40. Schmidt, B.; Lindman, S.; Tong, W.; Lindeberg, G.; Gogoli, A.; Lai, Z.; Thornwall, M.; Synnergren, B.; Nilsson, A.; Welch, C. J.; Sohtell, M.; Westerlund, C.; Nyberg, F.; Karlen, A.; Hallberg, A. J. Med. Chem. 1997, 40, 903-919.
41. Ellman, G. L. Arch. Biochem. Biophys. 1958, 74, 443-450.
42. Munshi, S.; Hall, D. L.; Kornienko, M.; Darke, P. L.; Kuo, L. C. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2003, 59, 1725-1730.
43. Nefzi, A.; Dooley, C.; Ostresh, J. M.; Houghten, R. A. Bioorg. Med. Chem. Lett. 1998, 8, 2273-2278.
44. Reichwein, J. F.; Liskamp, R. M. J. Eur. J. Org. Chem. 2000, 2335-2344.
45. Gable, K. L.; Maddux, B. A.; Penaranda, C.; Zavodovskaya, M.; Campbell, M. J.; Lobo, M.; Robinson, L.; Schow, S.; Kerner, J. A.; Goldfine, I. D.; Youngren, J. F. Mol. Cancer Ther. 2006, 5, 1079-1086.
46. Kaiser, E.; Colescot, R. L.; Bossinge, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595-598.
47. Christensen, T. Acta Chem. Scand. B 1979, 33, 763-766.
48. Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 65, 355-360.
49. Aue, W. P.; Bartholdi, E.; Ernst, R. R. J. Chem. Phys. 1976, 64, 2229-2246.
50. Nagayama, K.; Kumar, A.; Wuthrich, K.; Ernst, R. R. J. Magn. Reson. 1980, 40, 321-334.
51. Macura, S.; Ernst, R. R. Mol. Phys. 1980, 41, 95-117.
52. Bax, A. Annu. Rev. Biochem. 1989, 58, 223-256.
53. Niv, M. Y.; Rubin, H.; Cohen, J.; Tsirulnikov, L.; Licht, T.; Peretzman-Shemer, A.; Cna'an, E.; Tartakovsky, A.; Stein, I.; Albeck, S.; Weinstein, I.; Goldenberg-Furmanov, M.; Tobi, D.; Cohen, E.; Laster, M.; Ben-Sasson, S. A.; Reuveni, H. J. Biol. Chem. 2004, 279, 1242-1255.