3-Aryl β-carbolin-1-ones as a new class of potent inhibitors of tumor cell proliferation: Synthesis and biological evaluation

Organic and Biomolecular Chemistry

Volumn 3, Issue 5, 2005, Pages 911-916

  Wang, Shaozhong ^a   Dong, Yanmei ^a   Wang, Xinyan ^a   Hu, Xiaoyi ^b   Liu, Jun O ^b   Hu, Yuefei ^a  

^a TSINGHUA UNIVERSITY   (China)

^b JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; CELLS; HYDROCHLORIC ACID; MOLECULAR STRUCTURE; NEUROLOGY; OPTIMIZATION; SYNTHESIS (CHEMICAL); TUMORS;

ATOM-SAVING; CELL PROLIFERATION; CYCLIZATION; KETONE-NITRILE ANNULATION;

AROMATIC COMPOUNDS;

ANTINEOPLASTIC AGENT; CARBOLINE DERIVATIVE; COPPER; CUPROUS ION; KETONE; NITRILE;

ARTICLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECT; HELA CELL; HUMAN; IC 50; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CARBOLINES; CELL PROLIFERATION; COPPER; CRYSTALLOGRAPHY, X-RAY; HELA CELLS; HUMANS; INHIBITORY CONCENTRATION 50; KETONES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITRILES;

EID: 15244359226     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b412921k     Document Type: Article

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48. For selected reports see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525-7546; (b) S. Wagaw, R. A. Rennels and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451-8458; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417-6418; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35-37; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101-1104; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035-2038; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681-3684; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043-6048.
49. For selected reports see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525-7546; (b) S. Wagaw, R. A. Rennels and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451-8458; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417-6418; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35-37; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101-1104; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035-2038; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681-3684; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043-6048.
50. For selected reports see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525-7546; (b) S. Wagaw, R. A. Rennels and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451-8458; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417-6418; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35-37; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101-1104; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035-2038; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681-3684; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043-6048.
51. For selected reports see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525-7546; (b) S. Wagaw, R. A. Rennels and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451-8458; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417-6418; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35-37; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101-1104; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035-2038; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681-3684; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043-6048.
52. For selected reports see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525-7546; (b) S. Wagaw, R. A. Rennels and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451-8458; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417-6418; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35-37; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101-1104; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035-2038; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681-3684; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043-6048.
53. For selected reports see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525-7546; (b) S. Wagaw, R. A. Rennels and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451-8458; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417-6418; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35-37; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101-1104; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035-2038; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681-3684; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043-6048.
54. For selected reports see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525-7546; (b) S. Wagaw, R. A. Rennels and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451-8458; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417-6418; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35-37; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101-1104; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035-2038; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681-3684; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043-6048.
55. For selected reports see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531-9542; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326-329; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439-3450; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 7727-7729; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421-7428; (f) K. Yamada, T. Kubo, H. Tokuyama and T. Fukuyama, Synlett, 2002, 231-234; (g) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630-6631.
56. For selected reports see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531-9542; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326-329; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439-3450; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 7727-7729; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421-7428; (f) K. Yamada, T. Kubo, H. Tokuyama and T. Fukuyama, Synlett, 2002, 231-234; (g) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630-6631.
57. For selected reports see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531-9542; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326-329; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439-3450; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 7727-7729; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421-7428; (f) K. Yamada, T. Kubo, H. Tokuyama and T. Fukuyama, Synlett, 2002, 231-234; (g) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630-6631.
58. For selected reports see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531-9542; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326-329; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439-3450; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 7727-7729; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421-7428; (f) K. Yamada, T. Kubo, H. Tokuyama and T. Fukuyama, Synlett, 2002, 231-234; (g) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630-6631.
59. For selected reports see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531-9542; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326-329; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439-3450; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 7727-7729; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421-7428; (f) K. Yamada, T. Kubo, H. Tokuyama and T. Fukuyama, Synlett, 2002, 231-234; (g) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630-6631.
60. For selected reports see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531-9542; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326-329; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439-3450; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 7727-7729; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421-7428; (f) K. Yamada, T. Kubo, H. Tokuyama and T. Fukuyama, Synlett, 2002, 231-234; (g) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630-6631.
61. For selected reports see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531-9542; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326-329; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439-3450; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2001, 123, 7727-7729; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421-7428; (f) K. Yamada, T. Kubo, H. Tokuyama and T. Fukuyama, Synlett, 2002, 231-234; (g) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630-6631.
62. O. A. Moe and D. T. Warner, J. Am. Chem. Soc., 1948, 70, 2763-2765.
63. For selected reports see: (a) L. Cheng, C. A. Goodwin, M. F. Schully, V. V. Kakkar and G. Claeson, J. Med. Chem., 1992, 35, 3364-3369; (b) C. Wang and H. I. Mosberg, Tetrahedron Lett., 1995, 36, 3623-3626; (c) D. Choi, J. P. Stables and H. Kohn, J. Med. Chem., 1996, 39, 1907-1916; (d) R. J. Smith, S. Bratovanov and S. Bieoz, Tetrahedron, 1997, 53, 13695-13702; (e) M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshino, K. Teshima, K. Chiba, S. Sasaki and T. Fujita, J. Med. Chem., 2000, 43, 2946-2961.
64. For selected reports see: (a) L. Cheng, C. A. Goodwin, M. F. Schully, V. V. Kakkar and G. Claeson, J. Med. Chem., 1992, 35, 3364-3369; (b) C. Wang and H. I. Mosberg, Tetrahedron Lett., 1995, 36, 3623-3626; (c) D. Choi, J. P. Stables and H. Kohn, J. Med. Chem., 1996, 39, 1907-1916; (d) R. J. Smith, S. Bratovanov and S. Bieoz, Tetrahedron, 1997, 53, 13695-13702; (e) M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshino, K. Teshima, K. Chiba, S. Sasaki and T. Fujita, J. Med. Chem., 2000, 43, 2946-2961.
65. For selected reports see: (a) L. Cheng, C. A. Goodwin, M. F. Schully, V. V. Kakkar and G. Claeson, J. Med. Chem., 1992, 35, 3364-3369; (b) C. Wang and H. I. Mosberg, Tetrahedron Lett., 1995, 36, 3623-3626; (c) D. Choi, J. P. Stables and H. Kohn, J. Med. Chem., 1996, 39, 1907-1916; (d) R. J. Smith, S. Bratovanov and S. Bieoz, Tetrahedron, 1997, 53, 13695-13702; (e) M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshino, K. Teshima, K. Chiba, S. Sasaki and T. Fujita, J. Med. Chem., 2000, 43, 2946-2961.
66. For selected reports see: (a) L. Cheng, C. A. Goodwin, M. F. Schully, V. V. Kakkar and G. Claeson, J. Med. Chem., 1992, 35, 3364-3369; (b) C. Wang and H. I. Mosberg, Tetrahedron Lett., 1995, 36, 3623-3626; (c) D. Choi, J. P. Stables and H. Kohn, J. Med. Chem., 1996, 39, 1907-1916; (d) R. J. Smith, S. Bratovanov and S. Bieoz, Tetrahedron, 1997, 53, 13695-13702; (e) M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshino, K. Teshima, K. Chiba, S. Sasaki and T. Fujita, J. Med. Chem., 2000, 43, 2946-2961.
67. For selected reports see: (a) L. Cheng, C. A. Goodwin, M. F. Schully, V. V. Kakkar and G. Claeson, J. Med. Chem., 1992, 35, 3364-3369; (b) C. Wang and H. I. Mosberg, Tetrahedron Lett., 1995, 36, 3623-3626; (c) D. Choi, J. P. Stables and H. Kohn, J. Med. Chem., 1996, 39, 1907-1916; (d) R. J. Smith, S. Bratovanov and S. Bieoz, Tetrahedron, 1997, 53, 13695-13702; (e) M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshino, K. Teshima, K. Chiba, S. Sasaki and T. Fujita, J. Med. Chem., 2000, 43, 2946-2961.
68. (a) S. Wang, G. Yu, J. Lu, K. Xiao, Y. Hu and H. Hu, Synthesis, 2003, 487-490;
69. (b) G. Yu, S. Wang, K. Wang, Y. Hu and H. Hu, Synthesis, 2004, 1021-1028.
70. 2 = 0.2036.