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Original Articles

Molecular docking-based 3D-QSAR studies of pyrrolo[3,4-c]pyrazole derivatives as Aurora-A inhibitors

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Pages 31-42 | Received 27 Aug 2009, Accepted 12 Aug 2010, Published online: 28 Jan 2011

References

  • Crane , R. , Gadea , B. , Littlepage , L. , Wu , H. and Ruderman , J.V. 2004 . Aurora A, meiosis and mitosis . Biol. Cell , 96 : 215 – 229 .
  • Tseng , T.C. , Chen , S.H. , Hsu , Y.P. and Tang , T.K. 1998 . Protein kinase profile of sperm and eggs: Cloning and characterization of two novel testis-specific protein kinases (AIE1, AIE2) related to yeast and fly chromosome segregation regulators . DNA Cell Biol. , 17 : 823 – 833 .
  • Kimura , M. , Kotani , S. , Hattori , T. , Sumi , N. , Yoshioka , T. , Todokoro , K. and Okano , Y. 1997 . Cell cycle-dependent expression and spindle pole localization of a novel human protein kinase, Aik, related to Aurora of Drosophila and yeast Ipl1 . J. Biol. Chem. , 272 : 13766 – 13771 .
  • Keen , N. and Taylor , S. 2004 . Aurora-kinase inhibitors as anticancer agents . Nat. Rev. Cancer , 4 : 927 – 936 .
  • Ditchfield , C. , Johnson , V.L. , Tighe , A. , Ellston , R. , Haworth , C. , Johnson , T. , Mortlock , A. , Keen , N. and Taylor , S. 2003 . Aurora B couples chromosome alignment with anaphase by targeting BubR1, Mad2, and Cenp-E to kinetochores . J. Cell Biol. , 161 : 267 – 280 .
  • Mortlock , A. , Keen , N.J. , Jung , F.H. , Heron , N.M. , Foote , K.M. , Wilkinson , R. and Green , S. 2005 . Progress in the development of selective inhibitors of Aurora kinases . Curr. Topp. Med. Chem. , 5 : 199 – 213 .
  • Harrington , E.A. , Bebbington , D. , Moore , J. , Rasmussen , R.K. , Ajose-Adeogun , A.O. , Nakayama , T. , Graham , J.A. , Demur , C. , Hercend , T. , Diu-Hercend , A. , Su , M. , Golec , J.M.C. and Miller , K.M. 2004 . VX-680, a potent and selective small-molecule inhibitor of the Aurora kinases, suppresses tumor growth in vivo . Nat. Med. , 10 : 262 – 267 .
  • Gontarewicz , A. , Balabanov , S. , Keller , G. , Colombo , R. , Graziano , A. , Pesenti , E. , Benten , D. , Bokemeyer , C. , Fiedler , W. , Moll , J. and Brummendorf , T.H. 2008 . Simultaneous targeting of Aurora kinases and Bcr-Abl kinase by the small molecule inhibitor PHA-739358 is effective against imatinib-resistant BCR-ABL mutations including T315I . Blood , 111 : 4355 – 4364 .
  • Deng , X.Q. , Wang , H.Y. , Zhao , Y.L. , Xiang , M.L. , Jiang , P.D. , Cao , Z.X. , Zheng , Y.Z. , Luo , S.D. , Yu , L.T. , Wei , Y.Q. and Yang , S.Y. 2008 . Pharmacophore modelling and virtual screening for identification of new Aurora-A kinase inhibitors . Chem. Biol. Drug Des. , 71 : 533 – 539 .
  • Wang , H.Y. , Li , L.L. , Cao , Z.X. , Luo , S.D. , Wei , Y.Q. and Yang , S.Y. 2009 . A specific pharmacophore model of Aurora B kinase inhibitors and virtual screening studies based on it . Chem. Biol. Drug Des. , 73 : 115 – 126 .
  • Zou , J. , Xie , H.Z. , Yang , S.Y. , Chen , J.J. , Ren , J.X. and Wei , Y.Q. 2008 . Towards more accurate pharmacophore modeling: Multicomplex-based comprehensive pharmacophore map and most-frequent-feature pharmacophore model of CDK2 . J. Mol. Graph. Model. , 27 : 430 – 438 .
  • Talele , T.T. and McLaughlin , M.L. 2008 . Molecular docking/dynamics studies of Aurora A kinase inhibitors . J. Mol. Graph. Model. , 26 : 1213 – 1222 .
  • Cramer , R.D. III , Patterson , D.E. and Bunce , J.D. 1988 . Comparative molecular-field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins . J. Am. Chem. Soc. , 110 : 5959 – 5967 .
  • Klebe , G. , Abraham , U. and Mietzner , T. 1994 . Molecular similarity indexes in a comparative-analysis (COMSIA) of drug molecules to correlate and predict their biological-activity . J. Med. Chem. , 37 : 4130 – 4146 .
  • Fancelli , D. , Berta , D. , Bindi , S. , Cameron , A. , Cappella , P. , Carpinelli , P. , Catana , C. , Forte , B. , Giordano , P. , Giorgini , M.L. , Mantegani , S. , Marsiglio , A. , Meroni , M. , Moll , J. , Pittala , V. , Roletto , F. , Severino , D. , Soncini , C. , Storici , P. , Tonani , R. , Varasi , M. , Vulpetti , A. and Vianello , P. 2005 . Potent and selective Aurora inhibitors identified by the expansion of a novel scaffold for protein kinase inhibition . J. Med. Chem. , 48 : 3080 – 3084 .
  • Pevarello , P. , Fancelli , D. , Vulpetti , A. , Amici , R. , Villa , M. , Pittala , V. , Vianello , P. , Cameron , A. , Ciomei , M. , Mercurio , C. , Bischoff , J.R. , Roletto , F. , Varasi , M. and Brasca , M.G. 2006 . 3-Amino-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles: A new class of CDK2 inhibitors . Bioorg. Med. Chem. Lett. , 16 : 1074 – 1090 .
  • Fancelli , D. , Moll , J. , Varasi , M. , Bravo , R. , Artico , R. , Berta , D. , Bindi , S. , Cameron , A. , Candiani , I. , Cappella , P. , Carpinelli , P. , Croci , W. , Forte , B. , Giorgini , M.L. , Klapwijk , J. , Marsiglio , A. , Pesenti , E. , Rocchetti , M. , Roletto , F. , Severino , D. , Soncini , C. , Storici , P. , Tonani , R. , Zugnoni , P. and Vianello , P. 2006 . 1,4,5,6-Tetrahydropyrrolo[3,4-c]pyrazoles: Identification of a potent Aurora kinase inhibitor with a favorable antitumor kinase inhibition profile . J. Med. Chem. , 49 : 7247 – 7251 .
  • Brasca , M.G. , Albanese , C. , Amici , R. , Ballinari , D. , Corti , L. , Croci , V. , Fancelli , D. , Fiorentini , F. , Nesi , M. , Orsini , P. , Orzi , F. , Pastori , W. , Perrone , E. , Pesenti , E. , Pevarello , P. , Riccardi-Sirtori , F. , Roletto , F. , Roussel , P. , Varasi , M. , Vulpetti , A. and Mercurio , C. 2007 . 6-Substituted pyrrolo[3,4-c]pyrazoles: An improved class of CDK2 inhibitors . Chem. Med. Chem. , 2 : 841 – 852 .
  • 2001 . Sybyl Version 6.9 , St Louis, MO : Tripos Associates .
  • Clark , M. , Cramer , R.D. and Opdenbosch , N.V. 1989 . Validation of the general-purpose Tripos 5.2 force-field . J. Comput. Chem. , 10 : 982 – 1012 .
  • Hou , T.J. , Li , Y.Y. , Liao , N. and Xu , X.J. 2000 . Three-dimension quantitative structure–activity relationship analysis of some cinnamamides using comparative molecular similarity indices analysis (CoMSIA) . J. Mol. Model. , 6 : 438 – 455 .
  • Guo , Y.S. , Xiao , J.F. , Guo , Z.R. , Chu , F.M. , Cheng , Y.H. and Wu , S. 2005 . Exploration of a binding mode of indole amide analogues as potent histone deacetylase inhibitors and 3D-QSAR analyses . Bioorg. Med. Chem. , 13 : 5424 – 5434 .
  • Singh , J. , van Vlijmen , H. , Lee , W.C. , Liao , Y. , Lin , K.C. , Ateeq , H. , Cuervo , J. , Zimmerman , C. , Hammond , C. , Karpusas , M. , Palmer , R. , Chattopadhyay , T. and Adams , S.P. 2002 . 3D QSAR (COMFA) of a series of potent and highly selective VLA-4 antagonists . J. Comput. Aided Mol. Des. , 16 : 201 – 211 .

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