-
1
-
-
0029049468
-
-
D. M. Bollag, P. A. McQueeney, J. Zhu, O. Hensens, L. Koupal, J. Liesch, M. Goetz, E. Lazarides, C. M. Woods, Cancer Res. 1995, 55, 2325.
-
(1995)
Cancer Res.
, vol.55
, pp. 2325
-
-
Bollag, D.M.1
McQueeney, P.A.2
Zhu, J.3
Hensens, O.4
Koupal, L.5
Liesch, J.6
Goetz, M.7
Lazarides, E.8
Woods, C.M.9
-
2
-
-
0032483019
-
-
T.-C. Chou, X.-G. Zhang, A. Balog, D.-S. Su, D. Meng, K. Savin, J. R. Bertino, S. J. Danishefsky, Proc. Natl. Acad. Sci. USA 1998, 95, 9642.
-
(1998)
Proc. Natl. Acad. Sci. USA
, vol.95
, pp. 9642
-
-
Chou, T.-C.1
Zhang, X.-G.2
Balog, A.3
Su, D.-S.4
Meng, D.5
Savin, K.6
Bertino, J.R.7
Danishefsky, S.J.8
-
3
-
-
0032416734
-
-
T.-C. Chou, X.-G. Zhang, C. R. Harris, S. D. Kuduk, A. Balog, K. Savin, J. R. Bertino, S. J. Danishefsky, Proc. Natl. Acad. Sci. USA 1998, 95, 15 798.
-
(1998)
Proc. Natl. Acad. Sci. USA
, vol.95
, pp. 15798
-
-
Chou, T.-C.1
Zhang, X.-G.2
Harris, C.R.3
Kuduk, S.D.4
Balog, A.5
Savin, K.6
Bertino, J.R.7
Danishefsky, S.J.8
-
4
-
-
0033007667
-
-
L. Sepp-Lorenzino, A. Balog, D.-S. Su, D. Meng, N. Timaul, H. I. Scher, S. J. , Danishefsky, N. Rosen, Prostate Cancer Prostatic Dis. 1999, 2, 41.
-
(1999)
Prostate Cancer Prostatic Dis.
, vol.2
, pp. 41
-
-
Sepp-Lorenzino, L.1
Balog, A.2
Su, D.-S.3
Meng, D.4
Timaul, N.5
Scher, H.I.6
Danishefsky, S.J.7
Rosen, N.8
-
5
-
-
0033550167
-
-
R. Christina, C. R. Harris, S. J. Danishefsky, J. Org. Chem. 1999, 64, 8434.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 8434
-
-
Christina, R.1
Harris, C.R.2
Danishefsky, S.J.3
-
6
-
-
0030018666
-
-
K. Gerth, N. Bedorf, G. Höfle, H. Irschik, H. Reichenbach, J. Antibiot. 1996, 49, 560.
-
(1996)
J. Antibiot.
, vol.49
, pp. 560
-
-
Gerth, K.1
Bedorf, N.2
Höfle, G.3
Irschik, H.4
Reichenbach, H.5
-
7
-
-
0001448991
-
-
G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671;
-
(1996)
Angew. Chem.
, vol.108
, pp. 1671
-
-
Höfle, G.1
Bedorf, N.2
Steinmetz, H.3
Schomburg, D.4
Gerth, K.5
Reichenbach, H.6
-
9
-
-
33845476466
-
-
GBF, DE4138042 C2
-
G. Hoefle, N. Bedorf, K. Gerth, H. Reichenbach (GBF), DE4138042 C2, 1993.
-
(1993)
-
-
Hoefle, G.1
Bedorf, N.2
Gerth, K.3
Reichenbach, H.4
-
10
-
-
0001682838
-
-
A. Balog, D. Meng, T. Kamenecka, P. Bertinato, D.-S. Su, E. J. Sorensen, S. J. Danishefsky, Angew. Chem. 1996, 108, 2976;
-
(1996)
Angew. Chem.
, vol.108
, pp. 2976
-
-
Balog, A.1
Meng, D.2
Kamenecka, T.3
Bertinato, P.4
Su, D.-S.5
Sorensen, E.J.6
Danishefsky, S.J.7
-
12
-
-
0001125046
-
-
K. C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, Z. Yang, Angew. Chem. 1997, 109, 170;
-
(1997)
Angew. Chem.
, vol.109
, pp. 170
-
-
Nicolaou, K.C.1
He, Y.2
Vourloumis, D.3
Vallberg, H.4
Yang, Z.5
-
14
-
-
0001556960
-
-
D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm, M. Cordes, Angew. Chem. 1997, 109, 543;
-
(1997)
Angew. Chem.
, vol.109
, pp. 543
-
-
Schinzer, D.1
Limberg, A.2
Bauer, A.3
Böhm, O.M.4
Cordes, M.5
-
16
-
-
0030767001
-
-
K. C. Nicolaou, S. Ninkovic, F. Sarabia, D. Vourloumis, Y. He, H. Vallberg, M. R. V. Finlay, Z. Yang, J. Am. Chem. Soc. 1997, 119, 7974.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 7974
-
-
Nicolaou, K.C.1
Ninkovic, S.2
Sarabia, F.3
Vourloumis, D.4
He, Y.5
Vallberg, H.6
Finlay, M.R.V.7
Yang, Z.8
-
17
-
-
0030669587
-
-
D. Meng, P. Bertinato, A. Balog, D.-S. Su, T. Kamenecka, E. J. Sorensen, S. J. Danishefsky, J. Am. Chem. Soc. 1997, 119, 10 073.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 10073
-
-
Meng, D.1
Bertinato, P.2
Balog, A.3
Su, D.-S.4
Kamenecka, T.5
Sorensen, E.J.6
Danishefsky, S.J.7
-
18
-
-
0032844073
-
-
D. Schinzer, A. Bauer, J. Schieber, Chem. Eur. J. 1999, 5, 2492.
-
(1999)
Chem. Eur. J.
, vol.5
, pp. 2492
-
-
Schinzer, D.1
Bauer, A.2
Schieber, J.3
-
19
-
-
33845494017
-
-
E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, J. Am. Chem. Soc. 1997, 119, 2733.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 2733
-
-
Sorensen, E.J.1
Danishefsky, S.J.2
Zheng, Y.-H.3
Chou, T.-C.4
He, L.5
Horwitz, S.B.6
-
20
-
-
0035949548
-
-
R. B. Lichtner, A. Rotgeri, T. Bunte, B. Buchmann, J. Hoffmann, W. Schwede, W. Skuballa, U. Klar, Proc. Natl. Acad. Sci. USA 2001, 98, 11 743.
-
(2001)
Proc. Natl. Acad. Sci. USA
, vol.98
, pp. 11743
-
-
Lichtner, R.B.1
Rotgeri, A.2
Bunte, T.3
Buchmann, B.4
Hoffmann, J.5
Schwede, W.6
Skuballa, W.7
Klar, U.8
-
21
-
-
0034684787
-
-
In parallel, colleagues from Novartis had also replaced the side chain at C15 with bicyclic heteroaromatic groups: K.-H. Altmann, G. Bold, G. Caravatti, A. Flörsheimer, V. Guagnano, M. Wartmann, Bioorg. Med. Chem. Lett. 2000, 10, 2765.
-
(2000)
Bioorg. Med. Chem. Lett.
, vol.10
, pp. 2765
-
-
Altmann, K.-H.1
Bold, G.2
Caravatti, G.3
Flörsheimer, A.4
Guagnano, V.5
Wartmann, M.6
-
22
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33845505434
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note
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Since the IUPAC nomenclature of epothilone D is completely different from epothilone B we prefer to use the numbering depicted in Scheme 2 throughout the following discussions.
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23
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1642401832
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(Eds.: I. Ojima, G. D. Vite, K.-H. Altmann), Oxford University Press, New York
-
"Synthesis and biological activity of epothilones": U. Klar, W. Skuballa, B. Buchmann, W. Schwede, T. Bunte, J. Hoffmann, R. B. Lichtner in Anticancer Agents. Frontiers in Cancer Chemotherapy (Eds.: I. Ojima, G. D. Vite, K.-H. Altmann), Oxford University Press, New York, 2001, pp. 131-147.
-
(2001)
Anticancer Agents. Frontiers in Cancer Chemotherapy
, pp. 131-147
-
-
Klar, U.1
Skuballa, W.2
Buchmann, B.3
Schwede, W.4
Bunte, T.5
Hoffmann, J.6
Lichtner, R.B.7
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24
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33845492303
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note
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Compounds that inhibit the proliferation of tumor cells by 50% at concentrations below 100 nM are defined as active.
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25
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33845505949
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note
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Three other epothilones have been investigated in early clinical studies (phase I): Kos-1584 (Kosan/Roche), ABJ879 (Novartis), BMS 310705 (BMS).
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27
-
-
13844294082
-
-
U. Klar, B. Röhr, F. Kuczynski, W. Schwede, M. Berger, W. Skuballa, B. Buchmann, Synthesis 2005, 301.
-
(2005)
Synthesis
, pp. 301
-
-
Klar, U.1
Röhr, B.2
Kuczynski, F.3
Schwede, W.4
Berger, M.5
Skuballa, W.6
Buchmann, B.7
-
31
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33845479202
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note
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Only stereochemically homogeneous material obtained from the direct crystallization was used in the calculation. Additional product can be obtained from the mother liquor.
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-
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-
32
-
-
18744410664
-
-
E. Watkins, A. G. Chittiboyina, J.-C. Jung, M. A. Avery, Curr. Pharm. Des. 2005, 11, 1615.
-
(2005)
Curr. Pharm. Des.
, vol.11
, pp. 1615
-
-
Watkins, E.1
Chittiboyina, A.G.2
Jung, J.-C.3
Avery, M.A.4
-
35
-
-
0001448991
-
-
G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671;
-
(1996)
Angew. Chem.
, vol.108
, pp. 1671
-
-
Höfle, G.1
Bedorf, N.2
Steinmetz, H.3
Schomburg, D.4
Gerth, K.5
Reichenbach, H.6
-
37
-
-
0037425543
-
-
R. E. Taylor, Y. Chen, A. Beatty, D. C. Myles, Y. Zhou, J. Am. Chem. Soc. 2003, 125, 26.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 26
-
-
Taylor, R.E.1
Chen, Y.2
Beatty, A.3
Myles, D.C.4
Zhou, Y.5
-
38
-
-
33845503838
-
-
note
-
See supporting information.
-
-
-
-
39
-
-
0034895987
-
-
F. Y. F. Lee, R. Borzilleri, C. R. Fairchild, S.-H. Kim, B. H. Long, C. Reventos-Suarez, G. D. Vite, W. C. Rose, R. A. Kramer, Clin. Cancer Res. 2001, 7, 1429.
-
(2001)
Clin. Cancer Res.
, vol.7
, pp. 1429
-
-
Lee, F.Y.F.1
Borzilleri, R.2
Fairchild, C.R.3
Kim, S.-H.4
Long, B.H.5
Reventos-Suarez, C.6
Vite, G.D.7
Rose, W.C.8
Kramer, R.A.9
-
40
-
-
0034692354
-
-
R. M. Borzilleri, X. Zheng, R. J. Schmidt, J. A. Johnson, S.-H. Kim, J. D. DiMarco, C. R. Fairchild, J. Z. Gougoutas, F. Y. Lee, B. H. Long, G. D. Vite, J. Am. Chem. Soc. 2000, 122, 8890.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 8890
-
-
Borzilleri, R.M.1
Zheng, X.2
Schmidt, R.J.3
Johnson, J.A.4
Kim, S.-H.5
DiMarco, J.D.6
Fairchild, C.R.7
Gougoutas, J.Z.8
Lee, F.Y.9
Long, B.H.10
Vite, G.D.11
-
43
-
-
33845495103
-
-
unpublished results
-
J. Hoffmann, B. Buchmann, W. Schwede, W. Skuballa, R.B. Lichtner, G. Siemeister, S. Hammer, K. Mittelstaedt, S. Winsel, J. Eschenbrenner, C. Demarche, U. Klar, unpublished results.
-
-
-
Hoffmann, J.1
Buchmann, B.2
Schwede, W.3
Skuballa, W.4
Lichtner, R.B.5
Siemeister, G.6
Hammer, S.7
Mittelstaedt, K.8
Winsel, S.9
Eschenbrenner, J.10
Demarche, C.11
Klar, U.12
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