Synthesis and conformational analysis of macrocyclic dihydroxystilbenes linked between the para-para positions

Chemistry - A European Journal

Volumn 13, Issue 25, 2007, Pages 7246-7256

  Mateo, Carmen ^a   López, Vilmarí ^a   Medarde, Manuel ^a   Peláez, Rafael ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Combretastatin analogue; Conformational analysis; Cyctophanes; Macrocycles

Indexed keywords

CONFORMATIONS; DERIVATIVES; MOLECULAR MODELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

COMBRETASTATIN ANALOGUE; CONFORMATIONAL ANALYSIS; CYCTOPHANES; MACROCYCLES;

PHENOLS;

ANTINEOPLASTIC AGENT; BIBENZYL DERIVATIVE; COMBRETASTATIN; STILBENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BIBENZYLS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34548336346     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700323     Document Type: Article

References (72)

1. a) C. J. Dinsmore, M. J. Bogusky, J. C. Culberson, J. M. Bergman, C. F. Homnick, C. B. Zartman, S. D. Mosser, M. D. Schaber, R. G. Robinson, K. S. Koblan, H. E. Huber, S. L. Graham, O. D. Hartman, J. R. Huff, T. M. Williams, J. Am. Chem. Soc. 2001, 123, 2107-2108;
2. b) C.-M. Park, T. Oie, A. M. Petros, H. Zhang, P. M. Nimmer, R. F. Henry, S. W. Elmore, J. Am. Chem. Soc. 2006, 128, 16206-16212;
3. c) V. J. Hruby, Acc. Chem. Res. 2001, 34, 389-397, and references therein.
4. L. Barboni, C. Lambertucci, G. Appendino, D. G. Vander Velde, R. H. Himes, E. Bombardelli, M. M. Wang, J. P. Snyder. J. Med. Chem. 2001, 44, 1576-1587.
5. a) A. Janecka, R. Kruszynski, Curr. Med. Chem. 2005, 12, 471-481;
6. b) X. R. Tian, T. B. Field, A. G. Switzer, A. W. Mazur, F. H. Ebetino, J. A. Wos, S. M. Berberich, L. R. Jayasinghe, C. M. Obringer, M. E. Dowty, B. B. Pinney, J. A. Farmer, D. Crossdoersen, R. J. Sheldon, J. Med. Chem. 2006, 49, 4745-4761.
7. H. Lu, R. B. Silverman, J Med Chem. 2006, 49, 7404-7412.
8. M. Watanabe, Y. Kazuta, H. Hayashi, S. Yamada, A. Matsuda, S. Shuto, J Med Chem. 2006, 49, 5587-5596.
9. a) N. H. Nam, Curr. Med. Chem. 2003, 10, 1697-1722;
10. b) M. Cushman, D. Nagarathnam, D. Gopal, A. K. Chakraborti, C. M. Lin, E. Hamel, J. Med. Chem. 1991, 34, 2579-2588;
11. c) G. R. Pettit, S. B. Singh, M. R. Boyd, E. Hamel, R. K. Pettit, J. M. Schmidt, F. Hogan, J. Med. Chem. 1995, 38, 1666-1672;
12. d) G. G. Dark, S. A. Hill, V. E. Prise, G. M. Tozer, G. R. Pettit, D. J. Chaplin, Cancer Res. 1997, 57, 1829-1834;
13. e) G. C. Tron, T. Pirali, G. Sorba, F. Pagliai, S. Busacca, A. A. Genazzani, J. Med. Chem. 2006, 49, 3033-3044.
14. C. M. Lin, H. H. Ho, G. R. Pettit, E. Hamel, Biochemistry 1989, 28, 6984-6991.
15. G. R. Pettit, G. M. Cragg, D. L. Herald, J. M. Schmidt, P. Lohavanijaya, Can. J. Chem. 1982, 60, 1374-1376.
16. a) P. Nandy, S. Banerjee, H. Gao, M. B. Hui, E. J. Lien, Pharm. Res. 1991, 8, 776-781;
17. b) C. M. Lin, S. B. Singh, P. S. Chu, R. O. Dempcy, J. M. Schmidt, G. R. Pettit, E. Hamel, Mol. Pharmacol. 1988, 34, 200-208;
18. c) M. L. Brown, J. M. Rieger, T. L. MacDonald. Bioorg. Med. Chem. 2000, 8, 1433-1441.
19. a) E. Gur, M. Kaftory, S. E. Biali, Z. Rappoport, J. Org. Chem. 1999, 64, 8144-8148;
20. b) R. Monaco, W. C. Gardiner, S. Kirschner, Int. Photogr. Int. J. Quant. Chem. 1999, 71, 57-62.
21. M. Cushman, D. Nagarathnam, D. Gopal, H. M. He, C. M. Lin, E. Hamel, J. Med. Chem. 1992, 35, 2293-2306.
22. R. Shirai, H. Takayama. A. Nishikawa, Y. Koiso, Y. Hashimoto, Bioorg. Med. Chem. Lett. 1998, 8, 1997-2000.
23. G. R. Pettit, J. W. Lippert III, D. L. Herald, E. Hamel, R. K. Pettit, J. Nat. Prod. 2000, 63, 969-974.
24. G. R. Pettit, B. E. Toki, D. L. Herald, M. R. Boyd, E. Hamel, R. K Pettit, J. C. Chapuis, J. Med. Chem. 1999, 42, 1459-1465.
25. R. B. G. Ravelli, B. Gigant, P. A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, M. Knossow, Nature 2004, 428. 198-202.
26. Y. Kim, M. A. Arai, T. Arai, J. O. Lamenzo, E. F. Dean, N. Patterson, P. A. Clemons, S. L. Schreiber, J. Am. Chem. Soc. 2004, 126, 14740-14745.
27. a) Lignans; B. Madrigal, P. Puebla, R. Peláez, E. Caballero, M. Medarde, J. Org. Chem. 2003, 68, 854-864;
28. b) indolocarbazole alkaloids: M. Adeva, H. Sahagun, E. Caballero, R. Peláez, M. Medarde, F. Tomé, J. Org. Chem. 2000, 65, 3387-3394;
29. c) combretastatins: C. Pérez-Melero, A. B. S. Maya, B. del Rey. R. Pelaez, E. Caballero, M. Medarde, Bioorg. Med. Chem. Lett. 2004, 14, 3771-3774;
30. d) A. B. S. Maya, C. Perez-Melero, C. Mateo, D. Alonso, J. L. Fernandez, C. Gajaite, F. Mollinedo, R. Pelaez, E. Caballero, M. Medarde, J. Med. Chem. 2005, 48, 556-568.
31. For representative stilbenophane references, see: a) P. Rajakumar, V. Murali, Tetrahedron 2004, 60, 2351-2360;
32. b) J. Gierschner, H. G. Mack, D. Oelkrug, I. Waldner, H. Rau, J. Phys. Chem. A 2004, 108, 257-263;
33. c) L. Ernst, Prog. Nucl. Magn. Reson. Spectrosc. 2000, 37, 4-190;
34. d) D. Tanner, O. Wennerstrom, Tetrahedron Lett. 1981, 22, 2313-2316.
35. For representative crownophane references, see: a) A. Furstner, G. Seidel, C. Kopiske, C. Kruger, R. Mynott, Liebigs Ann. 1996, 655-662;
36. b) K. Hiratani, N. Sakamoto, N. Kameta, M. Karikomia, Y. E. Nagawa, Chem. Commun. 2004, 1474-1475;
37. c) S. Inokuma, S. Sakai, J. Nishimura, Cyclophanes 1994, 172, 87-118;
38. d) S. Inokuma, T. Funaki, D. Hara, J. Nishimura, Heterocycles 2004, 63, 333-346;
39. e) N. G. Lukyanenko, T. I. Kirichenko, A. Y. Lyapunov, C. Y. Kulygina, Y. A. Siminov, M. S. Fonari, M. M. Botoshansky, Tetrahedron Lett. 2004, 45, 2927-2930.
40. a) C. Mateo, C. Pérez-Melero, R. Peláez, M. Medarde, J. Org. Chem. 2005, 70, 6544-6547;
41. b) C. Mateo, C. Pérez-Melero, R. Peláez, M. Medarde, Tetrahedron Lett. 2005, 46, 7055-7057.
42. a) F. Vögtle, P. Neumann, Tetrahedron 1970, 26, 5847-5873;
43. b) Cyclophanes, Vols. 1 and 2, (Eds. P. M. Keehn, S. M. Rosenfeld), Academic Press, New York, 1983;
44. c) F. Vögtle, Cyclophane Chemistry, Wiley, Chichester, UK, 1993.
45. a) D. Marquis, J. P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1995, 60, 7984-7996;
46. b) P. C. Hellier, J. S. Bradshaw, J. J. Young, X. X. Zhang, R. M. Izatt, J. Org. Chem. 1996, 61, 7270-7275;
47. c) H. Sharghi, M. A. Nasseri, K. Niknam, J. Org. Chem. 2001, 66, 7287-7293;
48. d) H. Sharghi, A. R. Massah, H. Eshghi, K. Niknam, J. Org. Chem. 1998, 63, 1455-1461;
49. e) A. J. Pearson, A. M. Gelormini, J. Org. Chem. 1995, 60, 281-284;
50. f) K. Komura. S. Itsuno, K. Ito, Chem. Commun. 1999, 35-36;
51. g) P. R. Ashton, V. Baldoni, V. Balzani, A. Credi, H. D. A. Hoffmann, M. V. Martínez-Díaz, F. M. Raymo, J. F. Stoddart, M. Venturi, Chem. Eur. J. 2001, 7, 3482-3493;
52. h) J. D. Badjic, V. Balzani, A. Crcdi, J. N. Lowe, S. Silvi, J. F. Stoddart, Chem. Eur. J. 2004, 10, 1926-1935;
53. i) P. R. Ashton, V. Balzani, J. Becher, A. Credi, M. C. T. Fyfe, G. Mattersteig, S. Menzer, M. B. Nielsen, F. M. Raymo, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1999, 121, 3951-3957.
54. V. Dvornikovs, B. E. House, M. Kaetzel, J. R. Dedman, D. B. Smithrud, J. Am. Chem. Soc. 2003, 125, 8290-8291.
55. S. Bartlett, G. S. Beddard, R. M. Jackson, V. Kayser, C. Kilner, A. Leach, A. Nelson, P. R. Oledzki, P. Parker, G. D. Reid, S. L. Warriner, J. Am. Chem. Soc. 2005, 127, 11699-11708, and references therein.
56. J. E. McMurry, Chem. Rev. 1989, 89, 1513-1524.
57. a) O. Mitsunobu, Synthesis 1981, 1-28;
58. b) D. L. Hughes, Org. React. 1992, 42, 335-656;
59. c) D. L. Hughes, Org. Prep. Proced. 1996, 28, 127-164.
60. a) G. M. Robertson, in Comprehensive Organic Synthesis: Carbon-Carbon a-Bond Formation, Pergamon Press, New York, 1991, pp. 563-611;
61. b) T. A. Lipski, A. Hilfoker, S. G. Nelson, J. Org. Chem. 1997, 62, 4566-4567.
62. J. E. McMurry, J. G. Rico, Tetrahedron Lett. 1989, 30, 1169-1172.
63. a) B. P. Mundy, R. Srinivasa, Y. Kim, T. Dolph, J. Org. Chem. 1982, 47, 1657-1661;
64. b) M. Nazaré, H. Waldmann, Chem. Eur. J. 2001, 7, 3363-3376.
65. Systematic conformational searches using Monte Carlo and MM2 and MM3 as molecular force fields were performed with Macromodel v. 5.1 and clustering of the resulting conformations with XCluster on Silicon Graphics workstations; the most stable conformations for the cis and trans glycols agree with the schematic drawings depicted in Scheme 11.
66. R. Shirai, T. Okabe, S. Iwasaki, Heterocycles 1997, 46, 145-148.
67. C for the protons of the tetrasubstituted ring ortho to the linker, and for chemically equivalent proton pairs; numbers are given so that the lower number is given to the more downfield shifted proton: e.g., δ(HA1)> δ(HA2) δ-(HB1) > δ(HB2) and so forth.
68. For a superposition of several alignments, see: http://web.usal.es/ ~pelaez/Pelaez/DIOLS.htm
69. W T. Pennington, S. Chakraborty, I. C. Paul, D. Y. Curtin, J. Am. Chem. Soc. 1988, 100, 6498-6504.
70. T. G. Momchilova, P. M. Ivanov, J. Mol. Struct. 1993, 288, 133-143.
71. a) J. K. Whitesell, M. A. Minton in Stereochemical Analysis of Alicyclic Compounds by NMR Spectroscopy, Chapman and Hall, New York, 1987, pp. 50-51;
72. b) G. Dyker, J. Körning, W. Stirner, Eur. J. Org. Chem. 1998, 1, 149-154.