SCOPUS 정보 검색 플랫폼

Volumn 8, Issue 9, 2013, Pages 1483-1494

Rational design of resorcylic acid lactone analogues as covalent MNK1/2 kinase inhibitors by tuning the reactivity of an enamide Michael acceptor

(7) Xu, Jin a,b Chen, Anqi a Joy, Joma c Xavier, Vanessa Joanne a Ong, Esther H Q c Hill, Jeffrey c Chai, Christina L L a,b

a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES (Singapore)

b NATIONAL UNIVERSITY OF SINGAPORE (Singapore)

c Agency for Science (Singapore)

Author keywords

Antitumor agents; Covalent inhibitors; Enamides; Kinases; Michael acceptors; Resorcylic acid lactones

Indexed keywords

ALPHA RESORCYLIC ACID; L 783277; LACTONE DERIVATIVE; MITOGEN ACTIVATED PROTEIN KINASE INTERACTING KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE INTERACTING KINASE 1 INHIBITOR; MITOGEN ACTIVATED PROTEIN KINASE INTERACTING KINASE 2; MITOGEN ACTIVATED PROTEIN KINASE INTERACTING KINASE 2 INHIBITOR; NATURAL PRODUCT; PROTEIN KINASE; PROTEIN KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; COVALENT BOND; DRUG DESIGN; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ANTITUMOR AGENTS; COVALENT INHIBITORS; ENAMIDES; KINASES; MICHAEL ACCEPTORS; RESORCYLIC ACID LACTONES;

AMIDES; CELL LINE, TUMOR; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HELA CELLS; HUMANS; INTRACELLULAR SIGNALING PEPTIDES AND PROTEINS; ISOMERISM; KINETICS; LACTONES; PROTEIN BINDING; PROTEIN KINASE INHIBITORS; PROTEIN-SERINE-THREONINE KINASES; RESORCINOLS;

EID: 84882948239 PISSN: 18607179 EISSN: 18607187 Source Type: Journal
DOI: 10.1002/cmdc.201300231 Document Type: Article

Times cited : (29)

References (51)

1
- 64349093749
- M. H. Potashman, M. E. Duggan, J. Med. Chem. 2009, 52, 1231-1246.
- (2009) J. Med. Chem. , vol.52 , pp. 1231-1246
- Potashman, M.H.¹ Duggan, M.E.²

2
- 79953314480
- J. Singh, R. C. Petter, T. A. Baillie, A. Whitty, Nat. Rev. Drug Discovery 2011, 10, 307-317.
- (2011) Nat. Rev. Drug Discovery , vol.10 , pp. 307-317
- Singh, J.¹ Petter, R.C.² Baillie, T.A.³ Whitty, A.⁴

3
- 77953631133
- D. S. Johnson, E. Weerapana, B. F. Cravatt, Future Med. Chem. 2010, 2, 949-964.
- (2010) Future Med. Chem. , vol.2 , pp. 949-964
- Johnson, D.S.¹ Weerapana, E.² Cravatt, B.F.³

4
- 84883046937

5
- 0030893008
- J. Singh, E. M. Dobrusin, D. W. Fry, T. Haske, A. Whitty, D. J. McNamara, J. Med. Chem. 1997, 40, 1130-1135;
- (1997) J. Med. Chem. , vol.40 , pp. 1130-1135
- Singh, J.¹ Dobrusin, E.M.² Fry, D.W.³ Haske, T.⁴ Whitty, A.⁵ McNamara, D.J.⁶

6
- 77949558462
- W. Zhou, W. Hur, U. McDermott, A. Dutt, W. Xian, S. B. Ficarro, J. Zhang, S. V. Sharma, J. Brugge, M. Meyerson, J. Settleman, N. S. Gray, Chem. Biol. 2010, 17, 285-295;
- (2010) Chem. Biol. , vol.17 , pp. 285-295
- Zhou, W.¹ Hur, W.² McDermott, U.³ Dutt, A.⁴ Xian, W.⁵ Ficarro, S.B.⁶ Zhang, J.⁷ Sharma, S.V.⁸ Brugge, J.⁹ Meyerson, M.¹⁰ Settleman, J.¹¹ Gray, N.S.¹²

7
- 0037413550
- A. Wissner, E. Overbeek, M. F. Reich, M. B. Floyd, B. D. Johnson, N. Mamuya, E. C. Rosfjord, C. Discafani, R. Davis, X. Shi, S. K. Rabindran, B. C. Gruber, F. Ye, W. A. Hallett, R. Nilakantan, R. Shen, Y.-F. Wang, L. M. Greenberger, H.-R. Tsou, J. Med. Chem. 2003, 46, 49-63;
- (2003) J. Med. Chem. , vol.46 , pp. 49-63
- Wissner, A.¹ Overbeek, E.² Reich, M.F.³ Floyd, M.B.⁴ Johnson, B.D.⁵ Mamuya, N.⁶ Rosfjord, E.C.⁷ Discafani, C.⁸ Davis, R.⁹ Shi, X.¹⁰ Rabindran, S.K.¹¹ Gruber, B.C.¹² Ye, F.¹³ Hallett, W.A.¹⁴ Nilakantan, R.¹⁵ Shen, R.¹⁶ Wang, Y.-F.¹⁷ Greenberger, L.M.¹⁸ Tsou, H.-R.¹⁹

8
- 78650513897
- M. Hagel, Nat. Chem. Biol. 2011, 7, 22-24;
- (2011) Nat. Chem. Biol. , vol.7 , pp. 22-24
- Hagel, M.¹

9
- 19744364796
- M. S. Cohen, C. Zhang, K. M. Shokat, J. Taunton, Science 2005, 308, 1318-1321.
- (2005) Science , vol.308 , pp. 1318-1321
- Cohen, M.S.¹ Zhang, C.² Shokat, K.M.³ Taunton, J.⁴

10
- 84859845948
- I. M. Serafimova, M. A. Pufall, S. Krishnan, K. Duda, M. S. Cohen, R. L. Maglathlin, J. M. McFarland, R. M. Miller, M. Frodin, J. Taunton, Nat. Chem. Biol. 2012, 8, 471-476.
- (2012) Nat. Chem. Biol. , vol.8 , pp. 471-476
- Serafimova, I.M.¹ Pufall, M.A.² Krishnan, S.³ Duda, K.⁴ Cohen, M.S.⁵ Maglathlin, R.L.⁶ McFarland, J.M.⁷ Miller, R.M.⁸ Frodin, M.⁹ Taunton, J.¹⁰

11
- 84865407060
- C.-U. Lee, T. N. Grossmann, Angew. Chem. 2012, 124, 8829-8831; Angew. Chem. Int. Ed. 2012, 51, 8699-8700.
- (2012) Angew. Chem. 2012, 124, 8829-8831; Angew. Chem. Int. Ed. , vol.51 , pp. 8699-8700
- Lee, C.-U.¹ Grossmann, T.N.²

12
- 84883039120

13
- 77956271160
- T. Ueda, M. Sasaki, A. J. Elia, I. I. C. Chio, K. Hamada, R. Fukunaga, T. W. Mak, Proc. Natl. Acad. Sci. USA 2010, 107, 13984-13990;
- (2010) Proc. Natl. Acad. Sci. USA , vol.107 , pp. 13984-13990
- Ueda, T.¹ Sasaki, M.² Elia, A.J.³ Chio, I.I.C.⁴ Hamada, K.⁵ Fukunaga, R.⁶ Mak, T.W.⁷

14
- 77956741769
- J. Oyarzabal, N. Zarich, M. I. Albarran, I. Palacios, M. Urbano-Cuadrado, G. Mateos, I. Reymundo, O. Rabal, A. Salgado, A. Corrionero, J. Fominaya, J. Pastor, J. R. Bischoff, J. Med. Chem. 2010, 53, 6618-6628.
- (2010) J. Med. Chem. , vol.53 , pp. 6618-6628
- Oyarzabal, J.¹ Zarich, N.² Albarran, M.I.³ Palacios, I.⁴ Urbano-Cuadrado, M.⁵ Mateos, G.⁶ Reymundo, I.⁷ Rabal, O.⁸ Salgado, A.⁹ Corrionero, A.¹⁰ Fominaya, J.¹¹ Pastor, J.¹² Bischoff, J.R.¹³

15
- 84883031323

16
- 77956275194
- N. Hay, Proc. Natl. Acad. Sci. USA 2010, 107, 13975-13976;
- (2010) Proc. Natl. Acad. Sci. USA , vol.107 , pp. 13975-13976
- Hay, N.¹

17
- 84879316511
- S. Lim, T. Y. Saw, M. Zhang, M. R. Jane, K. Nacro, J. Hill, A. Q. Lim, C.-T. Chang, D. A. Fruman, D. A. Rizzieri, S. Y. Tan, H. Fan, C. T. H. Chuah, S. T. Ong, Proc. Natl. Acad. Sci. USA 2013, 110, E2298-E2307.
- (2013) Proc. Natl. Acad. Sci. USA , vol.110
- Lim, S.¹ Saw, T.Y.² Zhang, M.³ Jane, M.R.⁴ Nacro, K.⁵ Hill, J.⁶ Lim, A.Q.⁷ Chang, C.-T.⁸ Fruman, D.A.⁹ Rizzieri, D.A.¹⁰ Tan, S.Y.¹¹ Fan, H.¹² Chuah, C.T.H.¹³ Ong, S.T.¹⁴

18
- 0030977269
- A. J. Waskiewicz, A. Flynn, C. G. Pround, J. A. Cooper, EMBO J. 1997, 16, 1909-1920.
- (1997) EMBO J. , vol.16 , pp. 1909-1920
- Waskiewicz, A.J.¹ Flynn, A.² Pround, C.G.³ Cooper, J.A.⁴

19
- 33645233076
- A. Schirmer, J. Kennedy, S. Murli, R. Reid, D. V. Santi, Proc. Natl. Acad. Sci. USA 2006, 103, 4234-4239.
- (2006) Proc. Natl. Acad. Sci. USA , vol.103 , pp. 4234-4239
- Schirmer, A.¹ Kennedy, J.² Murli, S.³ Reid, R.⁴ Santi, D.V.⁵

20
- 84882993313

21
- 0033380609
- A. Zhao, S. H. Lee, M. Mojena, R. G. Jenkins, D. R. Patrick, H. E. Huber, M. A. Goetz, O. D. Hensens, D. L. Zink, D. Vilella, A. W. Dombrowski, R. B. Lingham, L. Huang, J. Antibiot. 1999, 52, 1086-1094;
- (1999) J. Antibiot. , vol.52 , pp. 1086-1094
- Zhao, A.¹ Lee, S.H.² Mojena, M.³ Jenkins, R.G.⁴ Patrick, D.R.⁵ Huber, H.E.⁶ Goetz, M.A.⁷ Hensens, O.D.⁸ Zink, D.L.⁹ Vilella, D.¹⁰ Dombrowski, A.W.¹¹ Lingham, R.B.¹² Huang, L.¹³

22
- 70350511755
- P. Y. Dakas, R. Jogireddy, G. Valot, S. Barluenga, N. Winssinger, Chem. Eur. J. 2009, 15, 11490-11497.
- (2009) Chem. Eur. J. , vol.15 , pp. 11490-11497
- Dakas, P.Y.¹ Jogireddy, R.² Valot, G.³ Barluenga, S.⁴ Winssinger, N.⁵

23
- 0037903145
- J. Ninomiya-Tsuji, T. Kajino, K. Ono, T. Ohtomo, M. Matsumoto, M. Shiina, M. Mihara, M. Tsuchiya, K. Matsumoto, J. Biol. Chem. 2003, 278, 18485-18490.
- (2003) J. Biol. Chem. , vol.278 , pp. 18485-18490
- Ninomiya-Tsuji, J.¹ Kajino, T.² Ono, K.³ Ohtomo, T.⁴ Matsumoto, M.⁵ Shiina, M.⁶ Mihara, M.⁷ Tsuchiya, M.⁸ Matsumoto, K.⁹

24
- 51549120564
- G. Rastelli, R. Rosenfeld, R. Reid, D. V. Santi, J. Struct. Biol. 2008, 164, 18-23.
- (2008) J. Struct. Biol. , vol.164 , pp. 18-23
- Rastelli, G.¹ Rosenfeld, R.² Reid, R.³ Santi, D.V.⁴

25
- 84882953519

26
- 84875208605
- J. Wu, F. Powell, N. A. Larsen, Z. Lai, K. F. Byth, J. Read, R.-F. Gu, M. Roth, D. Toader, J. C. Saeh, H. Chen, ACS Chem. Biol. 2013, 8, 643-650;
- (2013) ACS Chem. Biol. , vol.8 , pp. 643-650
- Wu, J.¹ Powell, F.² Larsen, N.A.³ Lai, Z.⁴ Byth, K.F.⁵ Read, J.⁶ Gu, R.-F.⁷ Roth, M.⁸ Toader, D.⁹ Saeh, J.C.¹⁰ Chen, H.¹¹

27
- 77955497476
- R. Scholz, C. L. Sidler, R. F. Thali, N. Winssinger, P. C. F. Cheung, D. Neumann, J. Biol. Chem. 2010, 285, 25753-25766;
- (2010) J. Biol. Chem. , vol.285 , pp. 25753-25766
- Scholz, R.¹ Sidler, C.L.² Thali, R.F.³ Winssinger, N.⁴ Cheung, P.C.F.⁵ Neumann, D.⁶

28
- 84855292725
- A. Hamidi, V. vonBulow, R. Hamidi, N. Winssinger, S. Barluenga, C.-H. Heldin, M. Landstrom, J. Biol. Chem. 2012, 287, 123-133.
- (2012) J. Biol. Chem. , vol.287 , pp. 123-133
- Hamidi, A.¹ vonBulow, V.² Hamidi, R.³ Winssinger, N.⁴ Barluenga, S.⁵ Heldin, C.-H.⁶ Landstrom, M.⁷

29
- 84882961098

30
- 33845481603
- N. Winssinger, S. Barbluenga, Chem. Commun. 2007, 22-36;
- (2007) Chem. Commun. , pp. 22-36
- Winssinger, N.¹ Barbluenga, S.²

31
- 57049163500
- S. Barluenga, P.-Y. Dakas, M. Boulifa, E. Moulin, N. Winssinger, C. R. Chim. 2008, 11, 1306-1317;
- (2008) C. R. Chim. , vol.11 , pp. 1306-1317
- Barluenga, S.¹ Dakas, P.-Y.² Boulifa, M.³ Moulin, E.⁴ Winssinger, N.⁵

32
- 84882946605
- University of Strasbourg/CNRS, France PCT WO036299A1
- N. Winssinger, S. Barluenga, (University of Strasbourg/CNRS, France), PCT WO036299A1, 2011.
- (2011)
- Winssinger, N.¹ Barluenga, S.²

33
- 84883039726

34
- 77952109517
- Y. Shen, R. Boivin, N. Yoneda, H. Du, S. Schiller, T. Matsushima, M. Goto, H. Shirota, F. Gusovsky, C. Lemelin, Y. Jiang, Z. Zhang, R. Pelletier, M. Ikemori-Kawada, Y. Kawakami, A. Inoue, M. Schnaderbeck, Y. Wang, Bioorg. Med. Chem. Lett. 2010, 20, 3155-3157;
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 3155-3157
- Shen, Y.¹ Boivin, R.² Yoneda, N.³ Du, H.⁴ Schiller, S.⁵ Matsushima, T.⁶ Goto, M.⁷ Shirota, H.⁸ Gusovsky, F.⁹ Lemelin, C.¹⁰ Jiang, Y.¹¹ Zhang, Z.¹² Pelletier, R.¹³ Ikemori-Kawada, M.¹⁴ Kawakami, Y.¹⁵ Inoue, A.¹⁶ Schnaderbeck, M.¹⁷ Wang, Y.¹⁸

35
- 70350449262
- M. Goto, J. Chow, K. Muramoto, K. Chiba, S. Yamamoto, M. Fujita, H. Obaishi, K. Tai, Y. Mizui, I. Tanaka, D. Young, H. Yang, Y. J. Wang, H. Shirota, F. Gusovsky, J. Pharmacol. Exp. Ther. 2009, 331, 485-495.
- (2009) J. Pharmacol. Exp. Ther. , vol.331 , pp. 485-495
- Goto, M.¹ Chow, J.² Muramoto, K.³ Chiba, K.⁴ Yamamoto, S.⁵ Fujita, M.⁶ Obaishi, H.⁷ Tai, K.⁸ Mizui, Y.⁹ Tanaka, I.¹⁰ Young, D.¹¹ Yang, H.¹² Wang, Y.J.¹³ Shirota, H.¹⁴ Gusovsky, F.¹⁵

36
- 84882975071
- Eisai Inc., Clinicaltrials.gov ID: NCT00794781, November 19
- Eisai Inc., Clinicaltrials.gov ID: NCT00794781, November 19, 2008; http://clinicaltrials.gov/.
- (2008)

37
- 84882989332

38
- 77955591791
- S. Barluenga, R. Jogireddy, G. K. Koripelly, N. Winssinger, ChemBioChem 2010, 11, 1692-1699;
- (2010) ChemBioChem , vol.11 , pp. 1692-1699
- Barluenga, S.¹ Jogireddy, R.² Koripelly, G.K.³ Winssinger, N.⁴

39
- 79952269716
- E. Leproult, S. Barluenga, D. Moras, J.-M. Wurtz, N. Winssinger, J. Med. Chem. 2011, 54, 1347-1355.
- (2011) J. Med. Chem. , vol.54 , pp. 1347-1355
- Leproult, E.¹ Barluenga, S.² Moras, D.³ Wurtz, J.-M.⁴ Winssinger, N.⁵

40
- 84875789074
- C. Zambaldo, K. K. Sadhu, G. Karthikeyan, S. Barluenga, J.-P. Daguer, N. Winssinger, Chem. Sci. 2013, 4, 2088-2092.
- (2013) Chem. Sci. , vol.4 , pp. 2088-2092
- Zambaldo, C.¹ Sadhu, K.K.² Karthikeyan, G.³ Barluenga, S.⁴ Daguer, J.-P.⁵ Winssinger, N.⁶

41
- 80052641774
- J. Xu, A. Chen, M.-L. Go, K. Nacro, B. Liu, C. L. Chai, ACS Med. Chem. Lett. 2011, 2, 662-666.
- (2011) ACS Med. Chem. Lett. , vol.2 , pp. 662-666
- Xu, J.¹ Chen, A.² Go, M.-L.³ Nacro, K.⁴ Liu, B.⁵ Chai, C.L.⁶

42
- 26444592983
- R. Jauch, S. Jäkel, C. Netter, K. Schreiter, B. Aicher, H. Jäckle, M. C. Wahl, Structure 2005, 13, 1559-1568.
- (2005) Structure , vol.13 , pp. 1559-1568
- Jauch, R.¹ Jäkel, S.² Netter, C.³ Schreiter, K.⁴ Aicher, B.⁵ Jäckle, H.⁶ Wahl, M.C.⁷

43
- 84882942118

44
- 70350509085
- R. Jogireddy, P. Y. Dakas, G. Valot, S. Barluenga, N. Winssinger, Chem. Eur. J. 2009, 15, 11498-11506;
- (2009) Chem. Eur. J. , vol.15 , pp. 11498-11506
- Jogireddy, R.¹ Dakas, P.Y.² Valot, G.³ Barluenga, S.⁴ Winssinger, N.⁵

45
- 77951686876
- R. Jogireddy, S. Barluenga, N. Winssinger, ChemMedChem 2010, 5, 670-673.
- (2010) ChemMedChem , vol.5 , pp. 670-673
- Jogireddy, R.¹ Barluenga, S.² Winssinger, N.³

46
- 41549118967
- J. Tan, Z. Zhang, Z. Wang, Org. Biomol. Chem. 2008, 6, 1344-1348.
- (2008) Org. Biomol. Chem. , vol.6 , pp. 1344-1348
- Tan, J.¹ Zhang, Z.² Wang, Z.³

47
- 78049500108
- C. Napolitano, P. McArdle, P. V. Murphy, J. Org. Chem. 2010, 75, 7404-7407.
- (2010) J. Org. Chem. , vol.75 , pp. 7404-7407
- Napolitano, C.¹ McArdle, P.² Murphy, P.V.³

48
- 78650855820
- C. Avonto, O. Taglialatela-Scafati, F. Pollastro, A. Minassi, V. DiMarzo, L. DePetrocellis, G. Appendino, Angew. Chem. 2011, 123, 487-491; Angew. Chem. Int. Ed. 2011, 50, 467-471.
- (2011) Angew. Chem. 2011, 123, 487-491; Angew. Chem. Int. Ed. , vol.50 , pp. 467-471
- Avonto, C.¹ Taglialatela-Scafati, O.² Pollastro, F.³ Minassi, A.⁴ DiMarzo, V.⁵ DePetrocellis, L.⁶ Appendino, G.⁷

49
- 78651510163
- M. Liniger, C. Neuhaus, T. Hofmann, L. Fransioli-Ignazio, M. Jordi, P. Drueckes, J. Trappe, D. Fabbro, K.-H. Atlmann, ACS Med. Chem. Lett. 2011, 2, 22-27.
- (2011) ACS Med. Chem. Lett. , vol.2 , pp. 22-27
- Liniger, M.¹ Neuhaus, C.² Hofmann, T.³ Fransioli-Ignazio, L.⁴ Jordi, M.⁵ Drueckes, P.⁶ Trappe, J.⁷ Fabbro, D.⁸ Atlmann, K.-H.⁹

50
- 27844500638
- J. L. Parra, M. Buxade, C. G. Proud, J. Biol. Chem. 2005, 280, 37623-37833.
- (2005) J. Biol. Chem. , vol.280 , pp. 37623-37833
- Parra, J.L.¹ Buxade, M.² Proud, C.G.³

51
- 79957812702
- S. Ayers, T. N. Graf, A. F. Adcock, D. J. Kroll, S. Matthew, E. J. C. deBlanco, Q. Shen, S. M. Swanson, M. C. Wani, C. J. Pearce, N. H. Oberlies, J. Nat. Prod. 2011, 74, 1126-1131.
- (2011) J. Nat. Prod. , vol.74 , pp. 1126-1131
- Ayers, S.¹ Graf, T.N.² Adcock, A.F.³ Kroll, D.J.⁴ Matthew, S.⁵ deBlanco, E.J.C.⁶ Shen, Q.⁷ Swanson, S.M.⁸ Wani, M.C.⁹ Pearce, C.J.¹⁰ Oberlies, N.H.¹¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.