SCOPUS 정보 검색 플랫폼

Volumn 8, Issue 7, 2013, Pages 1067-1085

The lab oddity prevails: Discovery of Pan-CDK inhibitor (R)-S-Cyclopropyl-S-(4-{[4-{[(1R,2R)-2-hydroxy-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)sulfoximide (BAY1000394) for the treatment of cancer

(12) Lücking, Ulrich a Jautelat, Rolf a Krüger, Martin a Brumby, Thomas a Lienau, Philip a Schäfer, Martina a Briem, Hans a Schulze, Julia a Hillisch, Alexander a Reichel, Andreas a Wengner, Antje Margret a Siemeister, Gerhard a

a BAYER PHARMA AG (Germany)

Author keywords

Antitumor agents; Biological activity; CDK; Medicinal chemistry; Sulfoximines

Indexed keywords

ANTINEOPLASTIC AGENT; BAY 1000394; BUTHIONINE SULFOXIMINE; CARBONATE DEHYDRATASE; CYCLOPROPYL[4 [[4[[[(1 ,2 ) 2 HYDROXY 1 METHYLPROPYL]OXY] 5 (TRIFLUOROMETHYL)PYRIMIDIN 2 YL]AMINO]PHENYL]SULFOXIMIDE; SULFONAMIDE; UNCLASSIFIED DRUG; ZK 304709;

ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG ABSORPTION; DRUG EFFICACY; DRUG ELIMINATION; DRUG IDENTIFICATION; DRUG SOLUBILITY; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; HUMAN; IC 50; INDIVIDUALITY; LIVER MICROSOME; MOUSE; NONHUMAN; PRIORITY JOURNAL; STEREOISOMERISM;

ANIMALS; ANTINEOPLASTIC AGENTS; CYCLIN-DEPENDENT KINASES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; FEMALE; HELA CELLS; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; NEOPLASMS, EXPERIMENTAL; PROTEIN KINASE INHIBITORS; PYRIMIDINES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFOXIDES; UTERINE CERVICAL NEOPLASMS;

EID: 84879785697 PISSN: 18607179 EISSN: 18607187 Source Type: Journal
DOI: 10.1002/cmdc.201300096 Document Type: Article

Times cited : (155)

References (50)

1
- 77953401049
- J. Wesierska-Gadek, I. Chamrad, V. Krystof, Future Med. Chem. 2009, 1, 1561-1581.
- (2009) Future Med. Chem. , vol.1 , pp. 1561-1581
- Wesierska-Gadek, J.¹ Chamrad, I.² Krystof, V.³

2
- 77955485400
- D. Parry, T. Guzi, F. Shanahan, N. Davis, D. Prabhavalkar, D. Wiswell, W. Seghezzi, K. Paruch, M. P. Dwyer, R. Doll, A. Nomeir, W. Windsor, T. Fischmann, Y. Wang, M. Oft, T. Chen, P. Kirschmeier, E. M. Lees, Mol. Cancer Ther. 2010, 9, 2344-2352.
- (2010) Mol. Cancer Ther. , vol.9 , pp. 2344-2352
- Parry, D.¹ Guzi, T.² Shanahan, F.³ Davis, N.⁴ Prabhavalkar, D.⁵ Wiswell, D.⁶ Seghezzi, W.⁷ Paruch, K.⁸ Dwyer, M.P.⁹ Doll, R.¹⁰ Nomeir, A.¹¹ Windsor, W.¹² Fischmann, T.¹³ Wang, Y.¹⁴ Oft, M.¹⁵ Chen, T.¹⁶ Kirschmeier, P.¹⁷ Lees, E.M.¹⁸

3
- 9444228344
- D. W. Fry, P. J. Harvey, P. R. Keller, W. L. Elliott, M. Meade, E. Trachet, M. Albassam, X. Zheng, W. R. Leopold, N. K. Pryer, P. L. Toogood, Mol. Cancer Ther. 2004, 3, 1427-1438.
- (2004) Mol. Cancer Ther. , vol.3 , pp. 1427-1438
- Fry, D.W.¹ Harvey, P.J.² Keller, P.R.³ Elliott, W.L.⁴ Meade, M.⁵ Trachet, E.⁶ Albassam, M.⁷ Zheng, X.⁸ Leopold, W.R.⁹ Pryer, N.K.¹⁰ Toogood, P.L.¹¹

4
- 0034665961
- S.-H. Chao, K. Fujinaga, J. E. Marion, R. Taube, E. A. Sausville, A. M. Senderowicz, B. M. Peterlin, D. H. Price, J. Biol. Chem. 2000, 275, 28345-28348.
- (2000) J. Biol. Chem. , vol.275 , pp. 28345-28348
- Chao, S.-H.¹ Fujinaga, K.² Marion, J.E.³ Taube, R.⁴ Sausville, E.A.⁵ Senderowicz, A.M.⁶ Peterlin, B.M.⁷ Price, D.H.⁸

5
- 77955495586
- C. Albanese, R. Alzani, N. Amboldi, N. Avanzi, D. Ballinari, M. G. Brasca, C. Festuccia, F. Fiorentini, G. Locatelli, W. Pastori, V. Patton, F. Roletto, F. Colotta, A. Galvani, A. Isacchi, J. Moll, E. Pesenti, C. Mercurio, M. Ciomei, Mol. Cancer Ther. 2010, 9, 2243-2254.
- (2010) Mol. Cancer Ther. , vol.9 , pp. 2243-2254
- Albanese, C.¹ Alzani, R.² Amboldi, N.³ Avanzi, N.⁴ Ballinari, D.⁵ Brasca, M.G.⁶ Festuccia, C.⁷ Fiorentini, F.⁸ Locatelli, G.⁹ Pastori, W.¹⁰ Patton, V.¹¹ Roletto, F.¹² Colotta, F.¹³ Galvani, A.¹⁴ Isacchi, A.¹⁵ Moll, J.¹⁶ Pesenti, E.¹⁷ Mercurio, C.¹⁸ Ciomei, M.¹⁹

6
- 33747128468
- G. Siemeister, U. Luecking, C. Wagner, K. Detjen, C. McCoy, K. Bosslet, Biomed. Pharmacother. 2006, 60, 269-272.
- (2006) Biomed. Pharmacother. , vol.60 , pp. 269-272
- Siemeister, G.¹ Luecking, U.² Wagner, C.³ Detjen, K.⁴ McCoy, C.⁵ Bosslet, K.⁶

7
- 67650073265
- S. Lapenna, A. Giordano, Nat. Rev. Drug Discovery 2009, 8, 547-566.
- (2009) Nat. Rev. Drug Discovery , vol.8 , pp. 547-566
- Lapenna, S.¹ Giordano, A.²

8
- 79960836823
- E. A. Musgrove, C. E. Caldon, J. Barraclough, A. Stone, R. L. Sutherland, Nat. Rev. Cancer 2011, 11, 558-572.
- (2011) Nat. Rev. Cancer , vol.11 , pp. 558-572
- Musgrove, E.A.¹ Caldon, C.E.² Barraclough, J.³ Stone, A.⁴ Sutherland, R.L.⁵

9
- 79959732195
- J. Schamberger, M. Grimm, A. Steinmeyer, A. Hillisch, Drug Discovery Today 2011, 16, 636-641.
- (2011) Drug Discovery Today , vol.16 , pp. 636-641
- Schamberger, J.¹ Grimm, M.² Steinmeyer, A.³ Hillisch, A.⁴

10
- 42949157650
- U. Lücking, G. Siemeister, M. Schäfer, H. Briem, M. Krüger, P. Lienau, R. Jautelat, ChemMedChem 2007, 2, 63-77.
- (2007) ChemMedChem , vol.2 , pp. 63-77
- Lücking, U.¹ Siemeister, G.² Schäfer, M.³ Briem, H.⁴ Krüger, M.⁵ Lienau, P.⁶ Jautelat, R.⁷

11
- 12444257368
- M. Anderson, J. F. Beattie, G. A. Breault, J. Breed, K. F. Byth, J. D. Culshaw, R. P. A. Ellston, S. Green, C. A. Minshull, R. A. Norman, R. A. Pauptit, J. Stanway, A. P. Thomas, P. J. Jewsbury, Bioorg. Med. Chem. Lett. 2003, 13, 3021-3026.
- (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 3021-3026
- Anderson, M.¹ Beattie, J.F.² Breault, G.A.³ Breed, J.⁴ Byth, K.F.⁵ Culshaw, J.D.⁶ Ellston, R.P.A.⁷ Green, S.⁸ Minshull, C.A.⁹ Norman, R.A.¹⁰ Pauptit, R.A.¹¹ Stanway, J.¹² Thomas, A.P.¹³ Jewsbury, P.J.¹⁴

12
- 20144388968
- S. Verma, D. Nagarathnam, J. Shao, L. Zhang, J. Zhao, Y. Wang, T. Li, E. Mull, I. Enyedy, C. Wang, Q. Zhu, M. Altieri, J. Jordan, T.-T.-A. Dang, S. Reddy, Bioorg. Med. Chem. Lett. 2005, 15, 1973-1977.
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1973-1977
- Verma, S.¹ Nagarathnam, D.² Shao, J.³ Zhang, L.⁴ Zhao, J.⁵ Wang, Y.⁶ Li, T.⁷ Mull, E.⁸ Enyedy, I.⁹ Wang, C.¹⁰ Zhu, Q.¹¹ Altieri, M.¹² Jordan, J.¹³ Dang, T.-T.-A.¹⁴ Reddy, S.¹⁵

13
- 84879784441
- Schering AG), WO 2002/096888
- T. Brumby, R. Jautelat, O. Prien, M. Schaefer, G. Siemeister, U. Luecking, (Schering AG), WO 2002/096888, 2002.
- (2002)
- Brumby, T.¹ Jautelat, R.² Prien, O.³ Schaefer, M.⁴ Siemeister, G.⁵ Luecking, U.⁶

14
- 84882088781
- Academic Press, Burlington
- E. H. Kerns, L. Di, Drug-like Properties: Concepts, Structure Design and Methods, Academic Press, Burlington, 2008, pp.276-286.
- (2008) Drug-like Properties: Concepts, Structure Design and Methods , pp. 276-286
- Kerns, E.H.¹ Di, L.²

15
- 0019382327
- W. F. Bayne, F. T. Tao, G. Rogers, L. C. Chu, F. Theeuwes, J. Pharm. Sci. 1981, 70, 75-81.
- (1981) J. Pharm. Sci. , vol.70 , pp. 75-81
- Bayne, W.F.¹ Tao, F.T.² Rogers, G.³ Chu, L.C.⁴ Theeuwes, F.⁵

16
- 53249100318
- J. S. Graham, R. Plummer, C. McCoy, K. Kowal, H. Wiesinger, K. Detjen, H. Calvert, B. Wiedenmann, J. Cassidy, Eur. J. Cancer 2008, 44, 2162-2168.
- (2008) Eur. J. Cancer , vol.44 , pp. 2162-2168
- Graham, J.S.¹ Plummer, R.² McCoy, C.³ Kowal, K.⁴ Wiesinger, H.⁵ Detjen, K.⁶ Calvert, H.⁷ Wiedenmann, B.⁸ Cassidy, J.⁹

17
- 84940363592
- E. N. Scott, A. L. Thomas, L. R. Molife, S. Ahmed, S. Blagden, P. C. Fong, K. Kowal, C. McCoy, H. Wiesinger, W. Steward, J. DeBono, Cancer Chemother. Pharmacol. 2009, 64, 425-429.
- (2009) Cancer Chemother. Pharmacol. , vol.64 , pp. 425-429
- Scott, E.N.¹ Thomas, A.L.² Molife, L.R.³ Ahmed, S.⁴ Blagden, S.⁵ Fong, P.C.⁶ Kowal, K.⁷ McCoy, C.⁸ Wiesinger, H.⁹ Steward, W.¹⁰ DeBono, J.¹¹

18
- 0010367592
- W. T. Caldwell, E. C. Kornfeld, J. Am. Chem. Soc. 1942, 64, 1695-1698.
- (1942) J. Am. Chem. Soc. , vol.64 , pp. 1695-1698
- Caldwell, W.T.¹ Kornfeld, E.C.²

19
- 37049153109
- H. Burton, W. A. Davy, J. Chem. Soc. 1948, 525-527.
- (1948) J. Chem. Soc. , pp. 525-527
- Burton, H.¹ Davy, W.A.²

20
- 84879784741
- Schering AG), WO 2003/076437
- U. Luecking, M. Krueger, R. Jautelat, O. Prien, G. Siemeister, A. Ernst, (Schering AG), WO 2003/076437, 2003.
- (2003)
- Luecking, U.¹ Krueger, M.² Jautelat, R.³ Prien, O.⁴ Siemeister, G.⁵ Ernst, A.⁶

21
- 0038149006
- A. Casini, F. Abbate, A. Scozzafava, C. T. Supuran, Bioorg. Med. Chem. Lett. 2003, 13, 2759-2763.
- (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 2759-2763
- Casini, A.¹ Abbate, F.² Scozzafava, A.³ Supuran, C.T.⁴

22
- 84879782288
- Schering AG), WO 2006/034872
- A. Cleve, U. Luecking, C. West, H. Briem, G. Siemeister, M. Krueger, R. Jautelat, P. Lienau, (Schering AG), WO 2006/034872, 2006.
- (2006)
- Cleve, A.¹ Luecking, U.² West, C.³ Briem, H.⁴ Siemeister, G.⁵ Krueger, M.⁶ Jautelat, R.⁷ Lienau, P.⁸

23
- 0011365269
- H. R. Bentley, E. E. McCermott, J. Pace, J. K. Whitehead, T. Moran, Nature 1949, 163, 675-676.
- (1949) Nature , vol.163 , pp. 675-676
- Bentley, H.R.¹ McCermott, E.E.² Pace, J.³ Whitehead, J.K.⁴ Moran, T.⁵

24
- 0033985468
- M. Reggelin, C. Zur, Synthesis 2000, 1-64.
- (2000) Synthesis , pp. 1-64
- Reggelin, M.¹ Zur, C.²

25
- 4243987802
- H. H. Bailey, Chem.-Biol. Interact. 1998, 111-112, 239-254.
- (1998) Chem.-Biol. Interact. , vol.111-112 , pp. 239-254
- Bailey, H.H.¹

26
- 9044254931
- P. J. O'Dwyer, T. C. Hamilton, F. P. LaCreta, J. M. Gallo, D. Kilpatrick, T. Halbherr, J. Brennan, M. A. Bookman, J. Hoffman, R. C. Young, R. L. Comis, R. F. Ozols, J. Clin. Oncol. 1996, 14, 249-256.
- (1996) J. Clin. Oncol. , vol.14 , pp. 249-256
- O'Dwyer, P.J.¹ Hamilton, T.C.² LaCreta, F.P.³ Gallo, J.M.⁴ Kilpatrick, D.⁵ Halbherr, T.⁶ Brennan, J.⁷ Bookman, M.A.⁸ Hoffman, J.⁹ Young, R.C.¹⁰ Comis, R.L.¹¹ Ozols, R.F.¹²

27
- 0023917674
- I. R. Ager, A. C. Barnes, G. W. Danswan, P. W. Hairsine, D. P. Kay, P. D. Kennewell, S. S. Matharu, P. Miller, P. Robson, D. A. Rowlands, R. Tully, R. Westwood, J. Med. Chem. 1988, 31, 1098-1115.
- (1988) J. Med. Chem. , vol.31 , pp. 1098-1115
- Ager, I.R.¹ Barnes, A.C.² Danswan, G.W.³ Hairsine, P.W.⁴ Kay, D.P.⁵ Kennewell, P.D.⁶ Matharu, S.S.⁷ Miller, P.⁸ Robson, P.⁹ Rowlands, D.A.¹⁰ Tully, R.¹¹ Westwood, R.¹²

28
- 0020450202
- R. Pothmann, Drugs Future 1982, 7, 478-480.
- (1982) Drugs Future , vol.7 , pp. 478-480
- Pothmann, R.¹

29
- 0001363277
- C. R. Johnson, M. Haake, C. W. Schroeck, J. Am. Chem. Soc. 1970, 92, 6594-6598.
- (1970) J. Am. Chem. Soc. , vol.92 , pp. 6594-6598
- Johnson, C.R.¹ Haake, M.² Schroeck, C.W.³

30
- 84879785153
- Schering AG), WO 2005/037800
- U. Luecking, M. Krueger, R. Jautelat, G. Siemeister, (Schering AG), WO 2005/037800, 2005.
- (2005)
- Luecking, U.¹ Krueger, M.² Jautelat, R.³ Siemeister, G.⁴

31
- 60449109522
- J. D. Oslob, S. A. Heumann, C. H. Yu, D. A. Allen, S. Baskaran, M. Bui, E. Delarosa, A. D. Fung, A. Hashash, J. Hau, S. Ivy, J. W. Jacobs, W. Lew, J. Maung, R. S. McDowell, S. Ritchie, M. J. Romanowski, J. A. Silverman, W. Yang, M. Zhong, T. Fuchs-Knotts, Bioorg. Med. Chem. Lett. 2009, 19, 1409-1412.
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 1409-1412
- Oslob, J.D.¹ Heumann, S.A.² Yu, C.H.³ Allen, D.A.⁴ Baskaran, S.⁵ Bui, M.⁶ Delarosa, E.⁷ Fung, A.D.⁸ Hashash, A.⁹ Hau, J.¹⁰ Ivy, S.¹¹ Jacobs, J.W.¹² Lew, W.¹³ Maung, J.¹⁴ McDowell, R.S.¹⁵ Ritchie, S.¹⁶ Romanowski, M.J.¹⁷ Silverman, J.A.¹⁸ Yang, W.¹⁹ Zhong, M.²⁰ Fuchs-Knotts, T.²¹ more..

32
- 79952804851
- M. Ishikawa, Y. Hashimoto, J. Med. Chem. 2011, 54, 1539-1554.
- (2011) J. Med. Chem. , vol.54 , pp. 1539-1554
- Ishikawa, M.¹ Hashimoto, Y.²

33
- 2542432021
- J. Olsen, P. Seiler, B. Wagner, H. Fischer, T. Tschopp, U. Obst-Sander, D. W. Banner, M. Kansy, K. Müller, F. Diederich, Org. Biomol. Chem. 2004, 2, 1339-1352.
- (2004) Org. Biomol. Chem. , vol.2 , pp. 1339-1352
- Olsen, J.¹ Seiler, P.² Wagner, B.³ Fischer, H.⁴ Tschopp, T.⁵ Obst-Sander, U.⁶ Banner, D.W.⁷ Kansy, M.⁸ Müller, K.⁹ Diederich, F.¹⁰

34
- 38049033180
- N. V. Kondratenko, O. A. Radchenko, L. M. Yagupol'ski, J. Org. Chem. USSR 1984, 20, 2051-2052.
- (1984) J. Org. Chem. USSR , vol.20 , pp. 2051-2052
- Kondratenko, N.V.¹ Radchenko, O.A.² Yagupol'ski, L.M.³

35
- 84879785813
- This method also gave very good results in other imination reactions, but was later abandoned due to safety concerns.
- This method also gave very good results in other imination reactions, but was later abandoned due to safety concerns.

36
- 2542470498
- H. Okamura, C. Bolm, Org. Lett. 2004, 6, 1305-1307.
- (2004) Org. Lett. , vol.6 , pp. 1305-1307
- Okamura, H.¹ Bolm, C.²

37
- 0000605378
- E. Block, A. Schwan, D. A. Dixon, J. Am. Chem. Soc. 1992, 114, 3492-3499.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 3492-3499
- Block, E.¹ Schwan, A.² Dixon, D.A.³

38
- 0031140114
- G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757-786.
- (1997) Chem. Rev. , vol.97 , pp. 757-786
- Prakash, G.K.S.¹ Yudin, A.K.²

39
- 84879785480
- Bayer Schering Pharma AG), EP 2179991
- U. Luecking, G. Siemeister, P. Lienau, R. Jautelat, J. Schulze, (Bayer Schering Pharma AG), EP 2179991, 2010.
- (2010)
- Luecking, U.¹ Siemeister, G.² Lienau, P.³ Jautelat, R.⁴ Schulze, J.⁵

40
- 84879786410
- Bayer Schering Pharma AG), EP 2179992
- U. Luecking, G. Siemeister, P. Lienau, R. Jautelat, J. Schulze, (Bayer Schering Pharma AG), EP 2179992, 2010.
- (2010)
- Luecking, U.¹ Siemeister, G.² Lienau, P.³ Jautelat, R.⁴ Schulze, J.⁵

41
- 84904274827

42
- 84867422165
- G. Siemeister, U. Luecking, A. M. Wengner, P. Lienau, W. Steinke, C. Schatz, D. Mumberg, K. Ziegelbauer, Mol. Cancer Ther. 2012, 11, 2265-2273;
- (2012) Mol. Cancer Ther. , vol.11 , pp. 2265-2273
- Siemeister, G.¹ Luecking, U.² Wengner, A.M.³ Lienau, P.⁴ Steinke, W.⁵ Schatz, C.⁶ Mumberg, D.⁷ Ziegelbauer, K.⁸

43
- 84879784695
- Bayer Schering Pharma AG), DE 102010014427
- U. Luecking, G. Siemeister, A. Wengner, (Bayer Schering Pharma AG), DE 102010014427, 2011.
- (2011)
- Luecking, U.¹ Siemeister, G.² Wengner, A.³

44
- 0014062860
- Y. Pocker, J. T. Stone, Biochemistry 1967, 6, 668-678.
- (1967) Biochemistry , vol.6 , pp. 668-678
- Pocker, Y.¹ Stone, J.T.²

45
- 0030599010
- M. Rarey, B. Kramer, T. Lengauer, G. Klebe, J. Mol. Biol. 1996, 261, 470-489.
- (1996) J. Mol. Biol. , vol.261 , pp. 470-489
- Rarey, M.¹ Kramer, B.² Lengauer, T.³ Klebe, G.⁴

46
- 84879787279
- SYBYL 6.7, Tripos Inc., 1699 S. Hanley Road, Suite 303, St.Louis, MO 63144-2913 (USA), 2000.
- SYBYL 6.7, Tripos Inc., 1699 S. Hanley Road, Suite 303, St.Louis, MO 63144-2913 (USA), 2000.

47
- 0029025445
- P. A. Boriack, D. W. Christianson, J. Kingery-Wood, G. M. Whitesides, J. Med. Chem. 1995, 38, 2286-2291.
- (1995) J. Med. Chem. , vol.38 , pp. 2286-2291
- Boriack, P.A.¹ Christianson, D.W.² Kingery-Wood, J.³ Whitesides, G.M.⁴

48
- 0037571112
- T. A. Halgren, J. Comput. Chem. 1996, 17, 490-519.
- (1996) J. Comput. Chem. , vol.17 , pp. 490-519
- Halgren, T.A.¹

49
- 84920325457
- J. Navaza, Acta Crystallogr. Sect. A 1994, 50, 157-163.
- (1994) Acta Crystallogr. Sect. A , vol.50 , pp. 157-163
- Navaza, J.¹

50
- 0013461295
- M. D. Winn, G. N. Murshudov, M. Z. Papiz, Methods Enzymol. 2003, 374, 300-321.
- (2003) Methods Enzymol. , vol.374 , pp. 300-321
- Winn, M.D.¹ Murshudov, G.N.² Papiz, M.Z.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.