Aerobic iron-based cross-dehydrogenative coupling enables efficient diversity-oriented synthesis of coumestrol-based selective estrogen receptor modulators

Chemistry - A European Journal

Volumn 19, Issue 40, 2013, Pages 13575-13583

  Kshirsagar, Umesh A ^a   Parnes, Regev ^a   Goldshtein, Hagit ^a   Ofir, Rivka ^a   Zarivach, Raz ^a   Pappo, Doron ^a  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

cross coupling; iron; natural products; structure activity relationships; total synthesis

Indexed keywords

CROSS-COUPLINGS; DIVERSITY-ORIENTED SYNTHESIS; MCF-7 BREAST CANCER CELLS; NATURAL PRODUCT SYNTHESIS; NATURAL PRODUCTS; SELECTIVE ESTROGEN RECEPTOR MODULATORS; STRUCTURE ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS;

CELLS; CHEMICAL REACTIONS;

IRON;

8 ACETAMIDO COUMESTROL; 8-ACETAMIDO-COUMESTROL; 9 ACETAMIDO COUMESTROL; 9-ACETAMIDO-COUMESTROL; ANTINEOPLASTIC AGENT; COUMESTROL; DRUG DERIVATIVE; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR ALPHA, HUMAN; IRON; SELECTIVE ESTROGEN RECEPTOR MODULATOR;

ARTICLE; BREAST TUMOR; CHEMICAL STRUCTURE; CHEMISTRY; CROSS-COUPLING; FEMALE; HUMAN; IC 50; NATURAL PRODUCTS; STRUCTURE-ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS; TUMOR CELL LINE;

CROSS-COUPLING; IRON; NATURAL PRODUCTS; STRUCTURE-ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; COUMESTROL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR MODULATORS; FEMALE; HUMANS; INHIBITORY CONCENTRATION 50; IRON; MOLECULAR STRUCTURE; RECEPTORS, ESTROGEN; SELECTIVE ESTROGEN RECEPTOR MODULATORS;

EID: 84884818578     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300389     Document Type: Article

References (91)

1. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215-1292
2. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780-1824
3. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2011, 111, 1293-1314.
4. C.-J. Li, Acc. Chem. Res. 2009, 42, 335-344.
5. W. Liu, J. Liu, D. Ogawa, Y. Nishihara, X. Guo, Z. Li, Org. Lett. 2011, 13, 6272-6275
6. H.-F. Jiang, J.-H. Li, Z.-W. Chen, Tetrahedron 2010, 66, 9721-9728
7. C. M. R. Volla, P. Vogel, Org. Lett. 2009, 11, 1701-1704
8. Y.-Z. Li, B.-J. Li, X.-Y. Lu, S. Lin, Z.-J. Shi, Angew. Chem. 2009, 121, 3875-3878
9. Angew. Chem. Int. Ed. 2009, 48, 3817-3820
10. C.-X. Song, G.-X. Cai, T. R. Farrell, Z.-P. Jiang, H. Li, L.-B. Gan, Z.-J. Shi, Chem. Commun. 2009, 6002-6004
11. X. Guo, S. Pan, J. Liu, Z. Li, J. Org. Chem. 2009, 74, 8848-8851
12. L. Zhao, C.-J. Li, Angew. Chem. 2008, 120, 7183-7186
13. Angew. Chem. Int. Ed. 2008, 47, 7075-7078
14. Z. Li, R. Yu, H. Li, Angew. Chem. 2008, 120, 7607-7610
15. Angew. Chem. Int. Ed. 2008, 47, 7497-7500
16. Y. Zhang, C.-J. Li, Eur. J. Org. Chem. 2007, 4654-4657
17. Y. Zhang, C.-J. Li, Angew. Chem. 2006, 118, 1983-1986
18. Angew. Chem. Int. Ed. 2006, 45, 1949-1952
19. Z. Li, D. S. Bohle, C.-J. Li, Proc. Natl. Acad. Sci. USA 2006, 103, 8928-8933
20. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 3672-3673
21. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 11810-11811
22. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968-6969.
23. H. Egami, K. Matsumoto, T. Oguma, T. Kunisu, T. Katsuki, J. Am. Chem. Soc. 2010, 132, 13633-13635.
24. P. A. Wender, B. L. Miller, Nature 2009, 460, 197-201.
25. K. C. Nicolaou, R. Reingruber, D. Sarlah, S. Brase, J. Am. Chem. Soc. 2009, 131, 2086-2087
26. M. P. DeMartino, K. Chen, P. S. Baran, J. Am. Chem. Soc. 2008, 130, 11546-11560
27. E. S. Krygowski, K. Murphy-Benenato, M. D. Shair, Angew. Chem. Int. Ed. 2008, 47, 1680-1684
28. P. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404-408
29. P. S. Baran, N. B. Ambhaikar, C. A. Guerrero, B. D. Hafensteiner, D. W. Lin, J. M. Richter, ARKIVOC 2006, 7, 310-325
30. R. H. Frazier, Jr., R. L. Harlow, J. Org. Chem. 1980, 45, 5408-5411.
31. A. A. O. Sarhan, C. Bolm, Chem. Soc. Rev. 2009, 38, 2730-2744.
32. D. Barton, A. Deflorin, O. Edwards, J. Chem. Soc. 1956, 530-534.
33. H. Eickhoff, G. Jung, A. Rieker, Tetrahedron 2001, 57, 353-364.
34. M. Chandrasekharam, B. Chiranjeevi, K. S. V. Gupta, B. Sridhar, J. Org. Chem. 2011, 76, 10229-10235
35. H.-P. Bi, W.-W. Chen, Y.-M. Liang, C.-J. Li, Org. Lett. 2009, 11, 3246-3249.
36. X. Guo, R. Yu, H. Li, Z. Li, J. Am. Chem. Soc. 2009, 131, 17387-17393.
37. R. Parnes, U. A. Kshirsagar, A. Werbeloff, C. Regev, D. Pappo, Org. Lett. 2012, 14, 3324-3327.
38. A. L. Ososki, E. J. Kennelly, Phytother. Res. 2003, 17, 845-869.
39. M. S. Kurzer, X. Xu, Annu. Rev. Nutr. 1997, 17, 353-381.
40. K. R. Price, G. R. Fenwick, Food Addit. Contam. 1985, 2, 73-106.
41. P. A. Melo, D. A. Pinheiro, H. D. Ricardo, F. F. A. Fernandes, M. A. Tomaz, C. Z. El-Kik, M. A. Strauch, F. T. F. da, D. N. Sifuentes, S. Calil-Elias, C. D. Buarque, F. V. Brito, P. R. R. Costa, S. A. J. M. Da Silva, Toxicon 2010, 55, 488-496.
42. K. W. Gaido, L. S. Leonard, S. Lovell, J. C. Gould, D. Babai, C. J. Portier, D. P. McDonnell, Toxicol. Appl. Pharmacol. 1997, 143, 205-212
43. C. C. Li, Z. X. Xie, Y. D. Zhang, J. H. Chen, Z. Yang, J. Org. Chem. 2003, 68, 8500-8504.
44. E. M. Bickoff, R. L. Lyman, A. L. Livingston, A. N. Booth, J. Am. Chem. Soc. 1958, 80, 3969-3971
45. E. M. Bickoff, A. N. Booth, R. L. Lyman, A. L. Livingston, C. R. Thompson, F. Deeds, Science 1957, 126, 969-970.
46. M. S. Kurzer, J. Nutr. 2003, 133, 1983S-1986S
47. S. Makela, V. L. Davis, W. C. Tally, J. Korkman, L. Salo, R. Vihko, R. Santti, K. S. Korach, Environ. Health Perspect. 1994, 102, 572-578.
48. N. Heldring, A. Pike, S. Andersson, J. Matthews, G. Cheng, J. Hartman, M. Tujague, A. Strom, E. Treuter, M. Warner, J. A. Gustafsson, Physiol. Rev. 2007, 87, 905-931
49. B. J. Deroo, K. S. Korach, J Clin Invest 2006, 116, 561-570.
50. J. K. Hess-Wilson, J. Boldison, K. E. Weaver, K. E. Knudsen, Breast Cancer Res. Treat. 2006, 96, 279-292
51. S. Gélinas, M.-G. Martinoli, J. Neurosci. Res. 2002, 70, 90-96
52. G. G. J. M. Kuiper, B. Carlsson, K. Grandien, E. Enmark, J. Häggblad, S. Nilsson, J.-Å. Gustafsson, Endocrinology 1997, 138, 863-870
53. G. G. J. M. Kuiper, J. G. Lemmen, B. Carlsson, J. C. Corton, S. H. Safe, P. T. van der Saag, B. van der Burg, J.-Å. Gustafsson, Endocrinology 1998, 139, 4252-4263.
54. C. Phillips, L. R. Roberts, M. Schade, R. Bazin, A. Bent, N. L. Davies, R. Moore, A. D. Pannifer, A. R. Pickford, S. H. Prior, C. M. Read, A. Scott, D. G. Brown, B. Xu, S. L. Irving, J. Am. Chem. Soc. 2011, 133, 9696-9699.
55. L. R. Roberts, D. Armor, C. Barker, A. Bent, K. Bess, A. Brown, D. A. Favor, D. Ellis, S. L. Irving, M. MacKenny, C. Phillips, N. Pullen, A. Stennett, L. Strand, M. Styles, Bioorg. Med. Chem. Lett. 2011, 21, 5680-5683.
56. A. K. Shiau, D. Barstad, J. T. Radek, M. J. Meyers, K. W. Nettles, B. S. Katzenellenbogen, J. A. Katzenellenbogen, D. A. Agard, G. L. Greene, Nat. Struct. Biol. 2002, 9, 359-364.
57. T. Yao, D. Yue, R. C. Larock, J. Org. Chem. 2005, 70, 9985-9989
58. N. Al-Maharik, N. P. Botting, Tetrahedron 2004, 60, 1637-1642
59. G. A. Kraus, N. Zhang, J. Org. Chem. 2000, 65, 5644-5646
60. K. Hiroya, N. Suzuki, A. Yasuhara, Y. Egawa, A. Kasano, T. Sakamoto, J. Chem. Soc. Perkin Trans. 1 2000, 4339-4346
61. R. Laschober, T. Kappe, Synthesis 1990, 387-388
62. S. B. Pandit, S. Y. Gadre, Synth. Commun. 1988, 18, 157-166
63. O. H. Emerson, E. M. Bickoff, J. Am. Chem. Soc. 1958, 80, 4381-4383.
64. C.-F. Chang, L.-Y. Yang, S.-W. Chang, Y.-T. Fang, Y.-J. Lee, Tetrahedron 2008, 64, 3661-3666
65. D.-H. Gong, C.-Z. Li, C.-Y. Yuan, Chin. J. Chem. 2010, 19, 522-527
66. A. J. M. da Silva, P. A. Melo, N. M. Silva, F. V. Brito, C. D. Buarque, D. V. de Souza, V. P. Rodrigues, E. S. Pocas, F. Noël, E. X. Albuquerque, P. R. Costa, Bioorg. Med. Chem. Lett. 2001, 11, 283-286
67. B. S. U. Rani, M. Darbarwar, J. Indian Chem. Soc. 1986, 63, 1060-1062
68. M. Darbarwar, V. Sundaramurthy, N. V. S. Rao, Proc.-Indian Acad. Sci., Sect. A 1974, 80, 93-96
69. H. W. Wanzlick, R. Gritzky, H. Heidepriem, Chem. Ber. 1963, 96, 305-307
70. C. Deschamps-Vallet, C. Mentzer, Compt. Rend. 1960, 251, 736-738.
71. L. Tang, Y. Pang, Q. Yan, L. Shi, J. Huang, Y. Du, K. Zhao, J. Org. Chem. 2011, 76, 2744-2752
72. A. L. Livingston, S. C. Witt, R. E. Lundin, E. M. Bickoff, J. Org. Chem. 1965, 30, 2353-2355.
73. Z. Li, L. Cao, C. J. Li, Angew. Chem. 2007, 119, 6625-6627
74. Angew. Chem. Int. Ed. 2007, 46, 6505-6507.
75. P. Liu, Z. Wang, J. Lin, X. Hu, Eur. J. Org. Chem. 2012, 1583-1589.
76. W. Liu, Y. Li, K. Liu, Z. Li, J. Am. Chem. Soc. 2011, 133, 10756-10759.
77. G. Zhang, Y. Zhang, R. Wang, Angew. Chem. 2011, 123, 10613-10616
78. Angew. Chem. Int. Ed. 2011, 50, 10429-10432.
79. C. A. Correia, C.-J. Li, Tetrahedron Lett. 2010, 51, 1172-1175.
80. H. Egami, T. Katsuki, J. Am. Chem. Soc. 2009, 131, 6082-6083
81. T. Oguma, T. Katsuki, J. Am. Chem. Soc. 2012, 134, 20017-20020.
82. F. Recupero, C. Punta, Chem. Rev. 2007, 107, 3800-3842.
83. S. H. Cho, M. S. Cheong, K. D. Jung, C. S. Kim, S. H. Han, Appl. Catal., A 2004, 267, 241-244.
84. K. Ramig, M. Englander, F. Kallashi, L. Livchits, J. Zhou, Tetrahedron Lett. 2002, 43, 7731-7734.
85. P. Ascenzi, A. Bocedi, M. Marino, Mol. Aspects Med. 2006, 27, 299-402.
86. E. S. Manas, R. J. Unwalla, Z. B. Xu, M. S. Malamas, C. P. Miller, H. A. Harris, C. Hsiao, T. Akopian, W.-T. Hum, K. Malakian, S. Wolfrom, A. Bapat, R. A. Bhat, M. L. Stahl, W. S. Somers, J. C. Alvarez, J. Am. Chem. Soc. 2004, 126, 15106-15119.
87. O. S. Wolfbeis, K. Schaffner, Photochem. Photobiol. 1980, 32, 143-148.
88. A. Cassetta, I. Krastanova, K. Kristan, M. Brunskole Švegelj, D. Lamba, T. Lanišnik Rižner, J. Stojan, Biochemical J. 2012, 441, 151-160.
89. E. W. Thompson, D. Katz, T. B. Shima, A. E. Wakeling, M. E. Lippman, R. B. Dickson, Cancer Res. 1989, 49, 6929-6934.
90. N. Dudai, Y. Weinstein, M. Krup, T. Rabinski, R. Ofir, Planta Med. 2005, 71, 484-488.
91. A. Matsumura, A. Ghosh, G. S. Pope, P. D. Darbre, J. Steroid Biochem. Mol. Biol. 2005, 94, 431-443.