3D-QSAR and docking studies of 3-Pyridine heterocyclic derivatives as potent PI3K/mTOR inhibitors

Journal of Molecular Structure

Volumn 1054-1055, Issue , 2013, Pages 107-116

  Yang, Wenjuan ^a   Shu, Mao ^a   Wang, Yuanqiang ^a   Wang, Rui ^a   Hu, Yong ^a   Meng, Lingxin ^a   Lin, Zhihua ^a,b  

^a CHONGQING UNIVERSITY OF TECHNOLOGY   (China)

^b CHONGQING UNIVERSITY   (China)

Author keywords

3D QSAR; CoMFA; CoMSIA; Docking; PI3K mTOR dual inhibitor

Indexed keywords

3D-QSAR; COMFA; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE-MOLECULAR-SIMILARITY-INDICES ANALYSIS; COMSIA; DUAL INHIBITORS; MAMMALIAN TARGET; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP;

ALIGNMENT; ANTIBIOTICS; COMPUTATIONAL CHEMISTRY; DOCKING; LIGANDS; THREE DIMENSIONAL;

ENZYME INHIBITION;

MAMMALIA;

EID: 84885540944     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2013.09.049     Document Type: Article

References (56)

1. T.L. Yuan, and L.C. Cantley Oncogene 27 2008 5497
2. A. Carracedo, and P.P. Pandolfi Oncogene 27 2008 5527
3. Ken Inoki, Michael N. Corradetti, and Kunliang Guan Nat. Genet. 37 2004 19
4. Romina Marone, Vladimir Cmiljanovic, Bernd Giese, and Matthias P. Wymann Biochim. Biophys. Acta (BBA) - Proteins Proteomics 1784 2008 159
5. Jeffrey A. Engelman, Ji Luo, and Lewis C. Cantley Nat. Rev. Genet. 7 2006 606
6. Pixu Liu, Hailing Cheng, Thomas M. Roberts, and Jean J. Zhao Nat. Rev. Drug Discovery 8 2009 627
7. Roy Katso, Klaus Okkenhaug, Khatereh Ahmadi, Sarah White, John Timms, and Michael D. Waterfield Ann. Rev. Cell Dev. Biol. 17 2001 615
8. Binghua Jiang, and Lingzhi Li Biochim. Biophys. Acta (BBA) - Proteins Proteomics 1784 2008 150
9. Yardena Samuels, Zhenghe Wang, Alberto Bardelli, Natalie Silliman, Janine Ptak, Steve Szabo, Hai Yan, Adi Gazdar, Steven M. Powell, Gregory J. Riggins, James K.V. Willson, Sanford Markowitz, Kenneth W. Kinzler, Bert Vogelstein, and Victor E. Velculescu Science 304 2004 554
10. Mariona Graupera, Julie Guillermet-Guibert, Lazaros C. Foukas, Li-Kun Phng, Robert J. Cain, Ashreena Salpekar, Wayne Pearce, Stephen Meek, Jaime Millan, Pedro R. Cutillas, Andrew J.H. Smith, Anne J. Ridley, Christiana Ruhrberg, Holger Gerhardt, and Bart Vanhaesebroeck Nature 453 2008 662
11. Reuben J. Shaw, and Lewis C. Cantley Nature 441 2006 424
12. Thomas Schöndorf, Martina Becker, Uwe-Jochen Göhring, Barbara Wappenschmidt, Hannelore Kolhagen, and Christian M. Kurbacher Anticancer Drugs 12 2001 797
13. Sanae Bouali, Anne-Sophie Chrétien, Carole Ramacci, Marie Rouyer, Philippe Becuwe, and Jean-Louis Merlin Oncol. Rep. 21 2009 731
14. Megan Cully, Han You, Arnold J. Levine, and Tak W. Mak1 Nat. Rev. Cancer 6 2006 184
15. Hua Yang, William Kong, Lili He, Jianjun Zhao, Joshua D. O'Donnell, Jiawang Wang, Robert M. Wenham, Domenico Coppola, Patricia A. Kruk, Santo V. Nicosia, and Jin Q. Cheng Cancer Res. 68 2008 425
16. Jing Li, Clifford Yen, Danny Liaw, Katrina Podsypanina, Shikha Bose, Steven I. Wang, Janusz Puc, Christa Miliaresis, Linda Rodgers, Richard McCombie, Sandra H. Bigner, Beppino C. Giovanella, Michael Ittmann, Ben Tycko, Hanina Hibshoosh, Michael H. Wigler, and Ramon Parsons Science 275 1997 1943
17. Yu Yonghao, Sang-Oh Yoon, George Poulogiannis, and Qian Yang Science 332 2011 1317
18. Pixu Liu, Hailing Cheng, Thomas M. Roberts, and Jean J. Zhao Nat. Rev. Drug Discovery 8 2009 627
19. A. Carracedo, and P.P. Pandolfi Oncogene 27 2008 5527
20. Vittoria Zinzalla, Daniele Stracka, Wolfgang Oppliger, and Michael N. Hall Cell 144 2011 757
21. Reuben J. Shaw, Katja A. Lamia, Debbie Vasquez, Seung-Hoi Koo, Nabeel Bardeesy, Ronald A. DePinho, Marc Montminy, and Lewis C. Cantley Science 310 2005 1642
22. Peggy P. Hsu, Seong A. Kang, Jonathan Rameseder, Yi Zhang, Kathleen A. Ottina, Daniel Lim, Timothy R. Peterson, Yongmun Choi, Nathanael S. Gray, Michael B. Yaffe, Jarrod A. Marto, and David M. Sabatini Science 332 2011 1317
23. Reuben J. Shaw, Nabeel Bardeesy, Brendan D. Manning, Lyle Lopez, Monica Kosmatka, Ronald A. DePinho, and Lewis C. Cantley Cancer Cell 6 2004 91
24. Ken Inoki, Tianqing Zhu, and Kunliang Guan Cell 115 2003 577
25. Nathan T. Ihle, and Garth Powis Mol. Cancer Ther. 8 2009 1
26. Romina Marone, Vladimir Cmiljanovic, Bernd Giese, and Matthias P. Wymann Biochim. Biophys. Acta (BBA) - Proteins Proteomics 1784 2008 159
27. Christoph M. Dehnhardt, Aranapakam M. Venkatesan, Efren Delos Santos, Zecheng Chen, Osvaldo Santos, Semiramis Ayral-Kaloustian, Natasja Brooijmans, Robert Mallon, Irwin Hollander, Larry Feldberg, Judy Lucas, Inder Chaudhary, Ker Yu, Jay Gibbons, Robert Abraham, and Tarek S. Mansour J. Med. Chem. 53 2010 798
28. Aranapakam M. Venkatesan, Christoph M. Dehnhardt, Efren Delos Santos, Zecheng Chen, Osvaldo Dos Santos, Semiramis Ayral-Kaloustian, Gulnaz Khafizova, Natasja Brooijmans, Robert Mallon, Irwin Hollander, Larry Feldberg, Judy Lucas, Ker Yu, James Gibbons, Robert T. Abraham, Inder Chaudhary, and Tarek S. Mansour J. Med. Chem. 53 2010 2636
29. Wei Xuan, Teng Shao, Yiping Li, and Sanqi Zhang Drugs Clinic 27 2012 133
30. Masahiko Hayakawa, Hiroyuki Kaizawa, Hiroyuki Moritomo, Tomonobu Koizumi, Takahide Ohishi, Mayumi Yamano, Minoru Okada, Mitsuaki Ohta, Shin-ichi Tsukamoto, Florence I. Raynaud, Paul Workman, Michael D. Waterfield, and Peter Parker Bioorg. Med. Chem. Lett. 17 2007 2438
31. Jonathan M. Large, Jane E. Torr, Florence I. Raynaud, Paul A. Clarke, Angela Hayes, Francesca di Stefano, Frederique Urban, Stephen J. Shuttleworth, Nahid Saghir, Peter Sheldrake, Paul Workman, and Edward McDonald Bioorg. Med. Chem. 19 2011 836
32. Adrian J. Folkes, Khatereh Ahmadi, Wendy K. Alderton, Sonia Alix, Stewart J. Baker, Gary Box, Irina S. Chuckowree, Paul A. Clarke, Paul Depledge, Suzanne A. Eccles, Lori S. Friedman, Angela Hayes, Timothy C. Hancox, Arumugam Kugendradas, Letitia Lensun, Pauline Moore, Alan G. Olivero, Jodie Pang, Sonal Patel, Giles H. Pergl-Wilson, Florence I. Raynaud, Anthony Robson, Nahid Saghir, Laurent Salphati, Sukhjit Sohal, Mark H. Ultsch, Melanie Valenti, Heidi J.A. Wallweber, Nan Chi Wan, Christian Wiesmann, Paul Workman, Alexander Zhyvoloup, Marketa J. Zvelebil, and Stephen J. Shuttleworth J. Med. Chem. 51 2008 5522
33. Stephan Wullschleger, Robbie Loewith, and Michael N. Hall Cell 124 2006 471
34. Aranapakam M. Venkatesan, Zecheng Chen, Osvaldo Dos Santos, Christoph Dehnhardt, Efren Delos Santos, Semiramis Ayral-Kaloustian, Robert Mallon, Irwin Hollander, Larry Feldberg, Judy Lucas, Ker Yu, Inder Chaudhary, and Tarek S. Mansour Bioorg. Med. Chem. Lett. 20 2010 5869
35. Violeta Serra, Ben Markman, Maurizio Scaltriti, Pieter J.A. Eichhorn, Vanesa Valero, Marta Guzman, Maria Luisa Botero, Elisabeth Llonch, Francesco Atzori, Serena Di Cosimo, Michel Maira, Carlos Garcia-Echeverria, Josep Lluis Parra, Joaquin Arribas, and José Baselga Cancer Res. 68 2008 8022
36. Steven D. Knight, Nicholas D. Adams, Joelle L. Burgess, Amita M. Chaudhari, Michael G. Darcy, Carla A. Donatelli, Juan I. Luengo, Ken A. Newlander, Cynthia A. Parrish, Lance H. Ridgers, Martha A. Sarpong, Stanley J. Schmidt, Glenn S. Van Aller, Jeffrey D. Carson, Melody A. Diamond, Patricia A. Elkins, Christine M. Gardiner, Eric Garver, Seth A. Gilbert, Richard R. Gontarek, Jeffrey R. Jackson, Kevin L. Kershner, Lusong Luo, Kaushik Raha, Christian S. Sherk, Chiu-Mei Sung, David Sutton, Peter J. Tummino, Ronald J. Wegrzyn, Kurt R. Auger, and Dashyant Dhanak ACS Med. Chem. Lett. 1 2010 39.s
37. Noel D. D'Angelo, Tae-Seong Kim, Kristin Andrews, Shon K. Booker, Sean Caenepeel, Kui Chen, Derin D'Amico, Dan Freeman, Jian Jiang, Longbin Liu, John D. McCarter, Tisha San Miguel, Erin L. Mullady, Michael Schrag, Raju Subramanian, Jin Tang, Robert C. Wahl, Ling Wang, Douglas A. Whittington, Tian Wu, Ning Xi, Yang Xu, Peter Yakowec, Kevin Yang, Leeanne P. Zalameda, Nancy Zhang, Paul Hughes, and Mark H. Norman J. Med. Chem. 54 2011 1789
38. Markian M. Stec, Kristin L. Andrews, Shon K. Booker, Sean Caenepeel, Daniel J. Freeman, Jian Jiang, Hongyu Liao, John McCarter, Erin L. Mullady, Tisha San Miguel, Raju Subramanian, Nuria Tamayo, Ling Wang, Kevin Yang, Leeanne P. Zalameda, Nancy Zhang, Paul E. Hughes, and Mark H. Norman J. Med. Chem. 54 2011 5174
39. Nobuko Nishimura, Aaron Siegmund, Longbin Liu, Kevin Yang, Marian C. Bryan, Kristin L. Andrews, Yunxin Bo, Shon K. Booker, Sean Caenepeel, Daniel Freeman, Hongyu Liao, John McCarter, Erin L. Mullady, Tisha San Miguel, Raju Subramanian, Nuria Tamayo, Ling Wang, Douglas A. Whittington, Leeanne Zalameda, Nancy Zhang, Paul E. Hughes, and Mark H. Norman J. Med. Chem. 54 2011 4735
40. Hengmiao Cheng, Shubha Bagrodia, Simon Bailey, Martin Edwards, Jacqui Hoffman, Qiyue Hu, Robert Kania, Daniel R. Knighton, Matthew A. Marx, Sacha Ninkovic, Shaoxian Sun, and Eric Zhang MedChemComm. 1 2010 139
41. Joseph R. Garlich, Pradip De, Nandini Dey, Jing Dong Su, Xiaodong Peng, Antoinette Miller, Ravoori Murali, Yiling Lu, Gordon B. Mills, Vikas Kundra, H.-K. Shu, Qiong Peng, and Donald L. Durden Cancer Res. 68 2008 206
42. Daniel P. Sutherlin, Linda Bao, Megan Berry, Georgette Castanedo, Irina Chuckowree, Jenna Dotson, Adrian Folks, Lori Friedman, Richard Goldsmith, Janet Gunzner, Timothy Heffron, John Lesnick, Cristina Lewis, Simon Mathieu, Jeremy Murray, Jim Nonomiya, Jodie Pang, Niel Pegg, Wei Wei Prior, Lionel Rouge, Laurent Salphati, Deepak Sampath, Qingping Tian, Vickie Tsui, Nan Chi Wan, Shumei Wang, BinQing Wei, Christian Wiesmann, Ping Wu, Bingyan Zhu, and Alan Olivero J. Med. Chem. 54 2011 7579
43. B. Markman, P.M. LoRusso, A. Patnaik, E. Heath, A.D. Laird, B. van Leeuwen, and J. Baselga Eur. J. Cancer Suppl. 6 2008 68
44. Alexander Golbraikh, and Alexander Tropsha J. Mol. Graph. Model. 20 2002 269
45. Richard D. Cramer, David E. Patterson, and Jeffrey D. Bunce J. Am. Chem. Soc. 110 1988 5959
46. Gerhard Klebe, Ute Abraham, and Thomas Mietzner J. Med. Chem. 37 1994 4130
47. Markus Böhm, J. Stürzebecher, and Gerhard Klebe J. Med. Chem. 42 1999 458
48. Jiaying Sun, Shaoxi Cai, Ning Yan, and Hu Mei Eur. J. Med. Chem. 45 2010 1008
49. C. Matthew, D.C. Richard III, and O. Van Nicole J. Comput. Chem. 10 1989 982
50. Jianling Liu, Hong Zhang, Zhengtao Xiao, Fangfang Wang, Xia Wang, and Yonghua Wang Int. J. Mol. Sci. 12 2011 1807
51. Hongyan Liu, Shushen Liu, Litang Qin, and Lingyun Mo J. Mol. Model. 15 2009 837
52. Huahui Zeng, and Huabei Zhang J. Mol. Graph. Model. 29 2010 54
53. Richard D. Cramer J. Med. Chem. 46 2003 374
54. Walter Lindberg, Jan-Aake Persson, and Svante Wold Anal. Chem. 55 1983 643
55. Yongjun Ji, Mao Shu, Yong Lin, Yuanqiang Wang, Rui Wang, Yong Hu, and Zhihua Lin J. Mol. Struct. 1045 2013 35
56. Oscar Mendez-Lucio, Jaime Perez-Villanueva, Antonio Romo-Mancillas, and Rafael Castillo Med. Chem. Commun. 2 2011 10