SCOPUS 정보 검색 플랫폼

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 21, 2012, Pages 6665-6670

Discovery of 4-morpholino-pyrimidin-6-one and 4-morpholino-pyrimidin-2-one- containing Phosphoinositide 3-kinase (PI3K) p110β isoform inhibitors through structure-based fragment optimisation

(8) Giordanetto, Fabrizio a Wållberg, Andreas a Cassel, Johan a Ghosal, Saswati a Kossenjans, Michael a Yuan, Zhong Qing a Wang, Xiaoping b Liang, Lifeng b

a ASTRAZENECA R AND D (Sweden)

b WUXI APPTEC (China)

Author keywords

Fragment based; Inhibitor; p110 ; Phosphoinositide 3 kinase; PI3K

Indexed keywords

4 MORPHOLINO PYRIMIDIN 2 ONE; 4 MORPHOLINO PYRIMIDIN 6 ONE; 9 (1 ANILINOETHYL) 7 METHYL 2 MORPHOLINOPYRIDO[1,2 A]PYRIMIDIN 4 ONE; PHOSPHATIDYLINOSITOL 3 KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG SELECTIVITY; IC 50; LIPOPHILICITY; STRUCTURE ACTIVITY RELATION;

DRUG DISCOVERY; ENZYME ACTIVATION; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MORPHOLINES; PEPTIDE FRAGMENTS; PHOSPHATIDYLINOSITOL 3-KINASES; PROTEIN BINDING; PROTEIN ISOFORMS; PYRIMIDINONES; SOLUBILITY;

EID: 84867578803 PISSN: 0960894X EISSN: 14643405 Source Type: Journal
DOI: 10.1016/j.bmcl.2012.08.101 Document Type: Article

Times cited : (19)

References (38)

1
- 11144358645
- Y. Samuels, Z. Wang, A. Bardelli, N. Silliman, J. Ptak, S. Szabo, H. Yan, A. Gazdar, S.M. Powell, G.J. Riggins, J.K. Willson, S. Markowitz, K.W. Kinzler, B. Vogelstein, and V.E. Velculescu Science 304 2004 554
- (2004) Science , vol.304 , pp. 554
- Samuels, Y.¹ Wang, Z.² Bardelli, A.³ Silliman, N.⁴ Ptak, J.⁵ Szabo, S.⁶ Yan, H.⁷ Gazdar, A.⁸ Powell, S.M.⁹ Riggins, G.J.¹⁰ Willson, J.K.¹¹ Markowitz, S.¹² Kinzler, K.W.¹³ Vogelstein, B.¹⁴ Velculescu, V.E.¹⁵

2
- 17144382038
- D.A. Levine, F. Bogomolniy, C.J. Yee, A. Lash, R.R. Barakat, P.I. Borgen, and J. Boyd Clin. Cancer Res. 11 2005 2875
- (2005) Clin. Cancer Res. , vol.11 , pp. 2875
- Levine, D.A.¹ Bogomolniy, F.² Yee, C.J.³ Lash, A.⁴ Barakat, R.R.⁵ Borgen, P.I.⁶ Boyd, J.⁷

3
- 29644444566
- D.B. Whyte, and S.L. Holbeck Biochem. Biophys. Res. Commun. 340 2006 469
- (2006) Biochem. Biophys. Res. Commun. , vol.340 , pp. 469
- Whyte, D.B.¹ Holbeck, S.L.²

4
- 0032590011
- L. Shayesteh, Y. Lu, W.L. Kuo, R. Baldocchi, T. Godfrey, C. Collins, D. Pinkel, B. Powell, G.B. Mills, and J.W. Gray Nat. Genet. 21 1999 99
- (1999) Nat. Genet. , vol.21 , pp. 99
- Shayesteh, L.¹ Lu, Y.² Kuo, W.L.³ Baldocchi, R.⁴ Godfrey, T.⁵ Collins, C.⁶ Pinkel, D.⁷ Powell, B.⁸ Mills, G.B.⁹ Gray, J.W.¹⁰

5
- 7444250290
- I.G. Campbell, S.E. Russell, D.Y. Choong, K.G. Montgomery, M.L. Ciavarella, C.S. Hooi, B.E. Cristiano, R.B. Pearson, and W.A. Phillips Cancer Res. 64 2004 7678
- (2004) Cancer Res. , vol.64 , pp. 7678
- Campbell, I.G.¹ Russell, S.E.² Choong, D.Y.³ Montgomery, K.G.⁴ Ciavarella, M.L.⁵ Hooi, C.S.⁶ Cristiano, B.E.⁷ Pearson, R.B.⁸ Phillips, W.A.⁹

6
- 21044454703
- S.P. Jackson, S.M. Schoenwaelder, I. Goncalves, W.S. Nesbitt, C.L. Yap, C.E. Wright, V. Kenche, K.E. Anderson, S.M. Dopheide, Y. Yuan, S.A. Sturgeon, H. Prabaharan, P.E. Thompson, G.E. Smith, P.R. Shepherd, N. Daniele, S. Kulkarni, B. Abbott, D. Saylik, C. Jones, L. Lu, S. Giuliano, S.C. Hughan, J.A. Angus, A.D. Robertson, and H.H. Salem Nat. Med. 11 2005 507
- (2005) Nat. Med. , vol.11 , pp. 507
- Jackson, S.P.¹ Schoenwaelder, S.M.² Goncalves, I.³ Nesbitt, W.S.⁴ Yap, C.L.⁵ Wright, C.E.⁶ Kenche, V.⁷ Anderson, K.E.⁸ Dopheide, S.M.⁹ Yuan, Y.¹⁰ Sturgeon, S.A.¹¹ Prabaharan, H.¹² Thompson, P.E.¹³ Smith, G.E.¹⁴ Shepherd, P.R.¹⁵ Daniele, N.¹⁶ Kulkarni, S.¹⁷ Abbott, B.¹⁸ Saylik, D.¹⁹ Jones, C.²⁰ more..

7
- 0034635452
- E. Hirsch, V.L. Katanaev, C. Garlanda, O. Azzolino, L. Pirola, L. Silengo, S. Sozzani, A. Mantovani, F. Altruda, and M.P. Wymann Science 287 2000 1049
- (2000) Science , vol.287 , pp. 1049
- Hirsch, E.¹ Katanaev, V.L.² Garlanda, C.³ Azzolino, O.⁴ Pirola, L.⁵ Silengo, L.⁶ Sozzani, S.⁷ Mantovani, A.⁸ Altruda, F.⁹ Wymann, M.P.¹⁰

8
- 11144354388
- K.D. Puri, T.A. Doggett, J. Douangpanya, Y. Hou, W.T. Tino, T. Wilson, T. Graf, E. Clayton, M. Turner, J.S. Hayflick, and T.G. Diacovo Blood 103 2004 3448
- (2004) Blood , vol.103 , pp. 3448
- Puri, K.D.¹ Doggett, T.A.² Douangpanya, J.³ Hou, Y.⁴ Tino, W.T.⁵ Wilson, T.⁶ Graf, T.⁷ Clayton, E.⁸ Turner, M.⁹ Hayflick, J.S.¹⁰ Diacovo, T.G.¹¹

9
- 0033604577
- B. Vanhaesebroeck, and M.D. Waterfield Exp. Cell. Res. 253 1999 239
- (1999) Exp. Cell. Res. , vol.253 , pp. 239
- Vanhaesebroeck, B.¹ Waterfield, M.D.²

10
- 84875674359
- doi
- Bradbury, R.H. doi: http://dx.doi.org/10.1002/0471266949.bmc214.
- Bradbury, R.H.¹

11
- 33646383684
- Z.A. Knight, B. Gonzalez, M.E. Feldman, E.R. Zunder, D.D. Goldenberg, O. Williams, R. Loewith, D. Stokoe, A. Balla, B. Toth, T. Balla, W.A. Weiss, R.L. Williams, and K.M. Shokat Cell 125 2006 733
- (2006) Cell , vol.125 , pp. 733
- Knight, Z.A.¹ Gonzalez, B.² Feldman, M.E.³ Zunder, E.R.⁴ Goldenberg, D.D.⁵ Williams, O.⁶ Loewith, R.⁷ Stokoe, D.⁸ Balla, A.⁹ Toth, B.¹⁰ Balla, T.¹¹ Weiss, W.A.¹² Williams, R.L.¹³ Shokat, K.M.¹⁴

12
- 34250704713
- C. Chaussade, G.W. Rewcastle, J.D. Kendall, W.A. Denny, K. Cho, L.M. Gronning, M.L. Chong, S.H. Anagnostou, S.P. Jackson, N. Daniele, and P.R. Shepherd Biochem. J. 404 2007 449
- (2007) Biochem. J. , vol.404 , pp. 449
- Chaussade, C.¹ Rewcastle, G.W.² Kendall, J.D.³ Denny, W.A.⁴ Cho, K.⁵ Gronning, L.M.⁶ Chong, M.L.⁷ Anagnostou, S.H.⁸ Jackson, S.P.⁹ Daniele, N.¹⁰ Shepherd, P.R.¹¹

13
- 49649087385
- S. Jia, Z. Liu, S. Zhang, P. Liu, L. Zhang, S. Hyun, L.J. Zhang, S. Signoretti, M. Loda, T.M. Roberts, and J.J. Zhao Nature 45 2008 776
- (2008) Nature , vol.45 , pp. 776
- Jia, S.¹ Liu, Z.² Zhang, S.³ Liu, P.⁴ Zhang, L.⁵ Hyun, S.⁶ Zhang, L.J.⁷ Signoretti, S.⁸ Loda, M.⁹ Roberts, T.M.¹⁰ Zhao, J.J.¹¹

14
- 51349148948
- S. Wee, D. Wiederschain, S.M. Maira, A. Loo, C. Miller, R. deBeaumont, F. Stegmeier, Y.M. Yao, and C. Lengauer Proc. Natl. Acad. Sci. U.S.A. 105 2008 13057
- (2008) Proc. Natl. Acad. Sci. U.S.A. , vol.105 , pp. 13057
- Wee, S.¹ Wiederschain, D.² Maira, S.M.³ Loo, A.⁴ Miller, C.⁵ Debeaumont, R.⁶ Stegmeier, F.⁷ Yao, Y.M.⁸ Lengauer, C.⁹

15
- 84861490514
- V. Certal, F. Halley, A. Virone-Oddos, C. Delorme, A. Karlsson, A. Rak, F. Thompson, B. Filoche-Rommé, Y. El-Ahmad, J.C. Carry, P.Y. Abecassis, P. Lejeune, L. Vincent, H. Bonnevaux, J.P. Nicolas, T. Bertrand, J.P. Marquette, N. Michot, T. Benard, P. Below, I. Vade, F. Chatreaux, G. Lebourg, F. Pilorge, O. Angouillant-Boniface, A. Louboutin, C. Lengauer, and L. Schio J. Med. Chem. 55 2012 4788
- (2012) J. Med. Chem. , vol.55 , pp. 4788
- Certal, V.¹ Halley, F.² Virone-Oddos, A.³ Delorme, C.⁴ Karlsson, A.⁵ Rak, A.⁶ Thompson, F.⁷ Filoche-Rommé, B.⁸ El-Ahmad, Y.⁹ Carry, J.C.¹⁰ Abecassis, P.Y.¹¹ Lejeune, P.¹² Vincent, L.¹³ Bonnevaux, H.¹⁴ Nicolas, J.P.¹⁵ Bertrand, T.¹⁶ Marquette, J.P.¹⁷ Michot, N.¹⁸ Benard, T.¹⁹ Below, P.²⁰ more..

16
- 84859826350
- R.M. Sanchez, K. Erhard, M.A. Hardwicke, H. Lin, J. McSurdy-Freed, R. Plant, K. Raha, C.M. Rominger, M.D. Schaber, M.D. Spengler, M.L. Moore, H. Yu, J.I. Luengo, R. Tedesco, and R.A. Rivero Bioorg. Med. Chem. Lett. 22 2012 3198
- (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 3198
- Sanchez, R.M.¹ Erhard, K.² Hardwicke, M.A.³ Lin, H.⁴ McSurdy-Freed, J.⁵ Plant, R.⁶ Raha, K.⁷ Rominger, C.M.⁸ Schaber, M.D.⁹ Spengler, M.D.¹⁰ Moore, M.L.¹¹ Yu, H.¹² Luengo, J.I.¹³ Tedesco, R.¹⁴ Rivero, R.A.¹⁵

17
- 84862800391
- H. Lin, K. Erhard, M.A. Hardwicke, J.I. Luengo, J.F. Mack, J. McSurdy-Freed, R. Plant, K. Raha, C.M. Rominger, R.M. Sanchez, M.D. Schaber, M.J. Schulz, M.D. Spengler, R. Tedesco, R. Xie, J.J. Zeng, and R.A. Rivero Bioorg. Med. Chem. Lett. 22 2012 2230
- (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 2230
- Lin, H.¹ Erhard, K.² Hardwicke, M.A.³ Luengo, J.I.⁴ MacK, J.F.⁵ McSurdy-Freed, J.⁶ Plant, R.⁷ Raha, K.⁸ Rominger, C.M.⁹ Sanchez, R.M.¹⁰ Schaber, M.D.¹¹ Schulz, M.J.¹² Spengler, M.D.¹³ Tedesco, R.¹⁴ Xie, R.¹⁵ Zeng, J.J.¹⁶ Rivero, R.A.¹⁷

18
- 84863845246
- H. Lin, M.J. Schulz, R. Xie, J. Zeng, J.I. Luengo, M.D. Squire, R. Tedesco, J. Qu, K. Erhard, J.F. Mack, K. Raha, R. Plant, C.M. Rominger, J.L. Ariazi, C.S. Sherk, M.D. Schaber, J. McSurdy-Freed, M.D. Spengler, C.B. Davis, M.A. Hardwicke, and R.A. Rivero ACS Med. Chem. Lett. 3 2012 524
- (2012) ACS Med. Chem. Lett. , vol.3 , pp. 524
- Lin, H.¹ Schulz, M.J.² Xie, R.³ Zeng, J.⁴ Luengo, J.I.⁵ Squire, M.D.⁶ Tedesco, R.⁷ Qu, J.⁸ Erhard, K.⁹ MacK, J.F.¹⁰ Raha, K.¹¹ Plant, R.¹² Rominger, C.M.¹³ Ariazi, J.L.¹⁴ Sherk, C.S.¹⁵ Schaber, M.D.¹⁶ McSurdy-Freed, J.¹⁷ Spengler, M.D.¹⁸ Davis, C.B.¹⁹ Hardwicke, M.A.²⁰ Rivero, R.A.²¹ more..

19
- 80255137206
- J. Kim, S. Hong, and S. Hong Bioorg. Med. Chem. Lett. 21 2011 6977
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 6977
- Kim, J.¹ Hong, S.² Hong, S.³

20
- 71749111351
- S. Kim, P. Mangin, C. Dangelmaier, R. Lillian, S.P. Jackson, J.L. Daniel, and S.P. Kunapuli J. Biol. Chem. 284 2009 33763
- (2009) J. Biol. Chem. , vol.284 , pp. 33763
- Kim, S.¹ Mangin, P.² Dangelmaier, C.³ Lillian, R.⁴ Jackson, S.P.⁵ Daniel, J.L.⁶ Kunapuli, S.P.⁷

21
- 71749121027
- K. Gilio, I.C. Munnix, P. Mangin, J.M. Cosemans, M.A. Feijge, P.E. van der Meijden, S. Olieslagers, M.B. Chrzanowska-Wodnicka, R. Lillian, S. Schoenwaelder, S. Koyasu, S.O. Sage, S.P. Jackson, and J.W. Heemskerk J. Biol. Chem. 284 2009 33750
- (2009) J. Biol. Chem. , vol.284 , pp. 33750
- Gilio, K.¹ Munnix, I.C.² Mangin, P.³ Cosemans, J.M.⁴ Feijge, M.A.⁵ Van Der Meijden, P.E.⁶ Olieslagers, S.⁷ Chrzanowska-Wodnicka, M.B.⁸ Lillian, R.⁹ Schoenwaelder, S.¹⁰ Koyasu, S.¹¹ Sage, S.O.¹² Jackson, S.P.¹³ Heemskerk, J.W.¹⁴

22
- 35349030204
- S.M. Schoenwaelder, A. Ono, S. Sturgeon, S.M. Chan, P. Mangin, M.J. Maxwell, S. Turnbull, M. Mulchandani, K. Anderson, G. Kauffenstein, G.W. Rewcastle, J. Kendall, C. Gachet, H.H. Salem, and S.P. Jackson J. Biol. Chem. 282 2007 28648
- (2007) J. Biol. Chem. , vol.282 , pp. 28648
- Schoenwaelder, S.M.¹ Ono, A.² Sturgeon, S.³ Chan, S.M.⁴ Mangin, P.⁵ Maxwell, M.J.⁶ Turnbull, S.⁷ Mulchandani, M.⁸ Anderson, K.⁹ Kauffenstein, G.¹⁰ Rewcastle, G.W.¹¹ Kendall, J.¹² Gachet, C.¹³ Salem, H.H.¹⁴ Jackson, S.P.¹⁵

23
- 70349251723
- I. Canobbio, L. Stefanini, L. Cipolla, E. Ciraolo, C. Gruppi, C. Balduini, E. Hirsch, and M. Torti Blood 114 2009 2193
- (2009) Blood , vol.114 , pp. 2193
- Canobbio, I.¹ Stefanini, L.² Cipolla, L.³ Ciraolo, E.⁴ Gruppi, C.⁵ Balduini, C.⁶ Hirsch, E.⁷ Torti, M.⁸

24
- 77954710233
- A. Garcia, S. Kim, K. Bhavaraju, S.M. Schoenwaelder, and S.P. Kunapuli Biochem. J. 429 2010 369
- (2010) Biochem. J. , vol.429 , pp. 369
- Garcia, A.¹ Kim, S.² Bhavaraju, K.³ Schoenwaelder, S.M.⁴ Kunapuli, S.P.⁵

25
- 44149087073
- S.A. Sturgeon, C. Jones, J.A. Angus, and C.E. Wright Eur. J. Pharmacol. 587 2008 209
- (2008) Eur. J. Pharmacol. , vol.587 , pp. 209
- Sturgeon, S.A.¹ Jones, C.² Angus, J.A.³ Wright, C.E.⁴

26
- 78651258569
- F. Giordanetto, B. Kull, and A. Dellsén Bioorg. Med. Chem. Lett. 21 2011 829
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 829
- Giordanetto, F.¹ Kull, B.² Dellsén, A.³

27
- 0033581886
- E.H. Walker, O. Perisic, C. Ried, L. Stephens, and R.L. Williams Nature 402 1999 313
- (1999) Nature , vol.402 , pp. 313
- Walker, E.H.¹ Perisic, O.² Ried, C.³ Stephens, L.⁴ Williams, R.L.⁵

28
- 0033634827
- E.H. Walker, M.E. Pacold, O. Perisic, L. Stephens, P.T. Hawkins, M.P. Wymann, and R.L. Williams Mol. Cell. 6 2000 909
- (2000) Mol. Cell. , vol.6 , pp. 909
- Walker, E.H.¹ Pacold, M.E.² Perisic, O.³ Stephens, L.⁴ Hawkins, P.T.⁵ Wymann, M.P.⁶ Williams, R.L.⁷

29
- 75349106113
- A. Berndt, S. Miller, O. Williams, D.D. Le, B.T. Houseman, J.I. Pacold, F. Gorrec, W.C. Hon, Y. Liu, C. Rommel, P. Gaillard, T. Ruckle, M.K. Schwarz, K.M. Shokat, J.P. Shaw, and R.L. Williams Nat. Chem. Biol. 6 2010 117
- (2010) Nat. Chem. Biol. , vol.6 , pp. 117
- Berndt, A.¹ Miller, S.² Williams, O.³ Le, D.D.⁴ Houseman, B.T.⁵ Pacold, J.I.⁶ Gorrec, F.⁷ Hon, W.C.⁸ Liu, Y.⁹ Rommel, C.¹⁰ Gaillard, P.¹¹ Ruckle, T.¹² Schwarz, M.K.¹³ Shokat, K.M.¹⁴ Shaw, J.P.¹⁵ Williams, R.L.¹⁶

30
- 84867571000
- WO2006092143
- Tornoee, C.W.; Khanzhin, N.; Rottlaender, M.; Watson, W.P.; Greve, D.R. WO2006092143, 2006.
- (2006)
- Tornoee, C.-W.¹ Khanzhin, N.² Rottlaender, M.³ Watson, W.-P.⁴ Greve, D.-R.⁵

31
- 0005938083
- C. Kashima, A. Katoh, M. Shimizu, and Y. Omote Heterocycles 22 1984 2591
- (1984) Heterocycles , vol.22 , pp. 2591
- Kashima, C.¹ Katoh, A.² Shimizu, M.³ Omote, Y.⁴

32
- 84944034682
- A.R. Katritzky, C.W. Rees, Pergamon Oxford
- D.J. Brown A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry Vol. 3 1984 Pergamon Oxford 57
- (1984) Comprehensive Heterocyclic Chemistry , vol.3 , pp. 57
- Brown, D.J.¹

33
- 84875643393
- Interbioscreen Ltd., PO Box 218, Moscow, 119019, Russia
- Interbioscreen Ltd., PO Box 218, Moscow, 119019, Russia.

34
- 84875646004
- Aurora Fine Chemicals Ltd, Reininghausstrasse 49, Graz, A-8020, Austria
- Aurora Fine Chemicals Ltd, Reininghausstrasse 49, Graz, A-8020, Austria.

35
- 0043022253
- D. Montebugni, P. Bravo, E. Brenna, C. Mioskowski, W. Panzeri, F. Viani, A. Volonterio, A. Wagner, and M. Zanda Tetrahedron 59 2003 7147
- (2003) Tetrahedron , vol.59 , pp. 7147
- Montebugni, D.¹ Bravo, P.² Brenna, E.³ Mioskowski, C.⁴ Panzeri, W.⁵ Viani, F.⁶ Volonterio, A.⁷ Wagner, A.⁸ Zanda, M.⁹

36
- 0037068144
- G. Lou, L. Chen, and G.S. Poindexter Tetrahedron Lett. 43 2002 5739
- (2002) Tetrahedron Lett. , vol.43 , pp. 5739
- Lou, G.¹ Chen, L.² Poindexter, G.S.³

37
- 84867571944
- WO2006005914
- Bailey, J.P.; Giles, M.B.; Pass, M. WO2006005914, 2006.
- (2006)
- Bailey, J.-P.¹ Giles, M.-B.² Pass, M.³

38
- 65549113862
- H. Wan, and A.G. Holmén Comb. Chem. High Throughput Screen 12 2009 315
- (2009) Comb. Chem. High Throughput Screen , vol.12 , pp. 315
- Wan, H.¹ Holmén, A.G.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.