Literature DB >> 19362847

Design and synthesis of a novel tyrosine kinase inhibitor template.

P Jake Slavish1, Qin Jiang, Xiaoli Cui, Stephan W Morris, Thomas R Webb.   

Abstract

We report the design and synthesis of an insulin receptor kinase family-targeted inhibitor template using the inhibitor conformation observed in an IGF1R/inhibitor co-crystal complex by application of a novel molecular design approach that we have recently published. The synthesis of the template involves a one pot Opatz cyclization reaction that provides a versatile n class="Chemical">indole ester in good yields. We also developed the required chemistry to elaborate this template with additional substituents and have used this chemistry to prepare some initial compounds that show selective inhibition of anaplastic lymphoma kinase (ALK).

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Year:  2009        PMID: 19362847      PMCID: PMC2696309          DOI: 10.1016/j.bmc.2009.03.046

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  15 in total

1.  3-(2-aminoalkyl)-1-(2,6-difluorobenzyl)-5- (2-fluoro-3-methoxyphenyl)-6-methyl-uracils as orally bioavailable antagonists of the human gonadotropin releasing hormone receptor.

Authors:  Fabio C Tucci; Yun-Fei Zhu; Zhiqiang Guo; Timothy D Gross; Patrick J Connors; Yinghong Gao; Martin W Rowbottom; R Scott Struthers; Greg J Reinhart; Qiu Xie; Ta Kung Chen; Haig Bozigian; Anne L Killam Bonneville; Andrew Fisher; Liping Jin; John Saunders; Chen Chen
Journal:  J Med Chem       Date:  2004-07-01       Impact factor: 7.446

2.  Development of 6-substituted indolylquinolinones as potent Chek1 kinase inhibitors.

Authors:  Shaei Huang; Robert M Garbaccio; Mark E Fraley; Justin Steen; Constantine Kreatsoulas; George Hartman; Steve Stirdivant; Bob Drakas; Keith Rickert; Eileen Walsh; Kelly Hamilton; Carolyn A Buser; James Hardwick; Xianzhi Mao; Marc Abrams; Steve Beck; Weikang Tao; Rob Lobell; Laura Sepp-Lorenzino; Youwei Yan; Mari Ikuta; Joan Zugay Murphy; Vinod Sardana; Sanjeev Munshi; Lawrence Kuo; Michael Reilly; Elizabeth Mahan
Journal:  Bioorg Med Chem Lett       Date:  2006-09-20       Impact factor: 2.823

3.  Preparation of indoles from alpha-aminonitriles: A short synthesis of FGIN-1-27.

Authors:  Till Opatz; Dorota Ferenc
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

4.  Asymmetric carbon-carbon coupling of phenols or anilines with aryllead triacetates.

Authors:  Taichi Kano; Yuki Ohyabu; Susumu Saito; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2002-05-15       Impact factor: 15.419

5.  Design and synthesis of 5-aryl-pyridone-carboxamides as inhibitors of anaplastic lymphoma kinase.

Authors:  Rongshi Li; Liquan Xue; Tong Zhu; Qin Jiang; Xiaoli Cui; Zheng Yan; Danny McGee; Jian Wang; Vidyasagar Reddy Gantla; Jason C Pickens; Doug McGrath; Alexander Chucholowski; Stephan W Morris; Thomas R Webb
Journal:  J Med Chem       Date:  2006-02-09       Impact factor: 7.446

6.  Synthesis of methylene- and difluoromethylenephosphonate analogues of uridine-4-phosphate and 3-deazauridine-4-phosphate.

Authors:  Scott D Taylor; Farzad Mirzaei; Ali Sharifi; Stephen L Bearne
Journal:  J Org Chem       Date:  2006-12-08       Impact factor: 4.354

7.  Potent, orally active corticotropin-releasing factor receptor-1 antagonists containing a tricyclic pyrrolopyridine or pyrazolopyridine core.

Authors:  Brian Dyck; Dimitri E Grigoriadis; Raymond S Gross; Zhiqiang Guo; Mustapha Haddach; Dragan Marinkovic; James R McCarthy; Manisha Moorjani; Collin F Regan; John Saunders; Michael K Schwaebe; Tomas Szabo; John P Williams; Xiaohu Zhang; Haig Bozigian; Ta Kung Chen
Journal:  J Med Chem       Date:  2005-06-16       Impact factor: 7.446

8.  An orally available small-molecule inhibitor of c-Met, PF-2341066, exhibits cytoreductive antitumor efficacy through antiproliferative and antiangiogenic mechanisms.

Authors:  Helen Y Zou; Qiuhua Li; Joseph H Lee; Maria E Arango; Scott R McDonnell; Shinji Yamazaki; Tatiana B Koudriakova; Gordon Alton; Jingrong J Cui; Pei-Pei Kung; Mitchell D Nambu; Gerrit Los; Steven L Bender; Barbara Mroczkowski; James G Christensen
Journal:  Cancer Res       Date:  2007-05-01       Impact factor: 12.701

9.  Imidazole moiety replacements in the 3-(1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one inhibitors of insulin-like growth factor receptor-1 (IGF-1R) to improve cytochrome P450 profile.

Authors:  Upender Velaparthi; Peiying Liu; Balu Balasubramanian; Joan Carboni; Ricardo Attar; Marco Gottardis; Aixin Li; Ann Greer; Mary Zoeckler; Mark D Wittman; Dolatrai Vyas
Journal:  Bioorg Med Chem Lett       Date:  2007-03-19       Impact factor: 2.823

10.  Activating mutations in ALK provide a therapeutic target in neuroblastoma.

Authors:  Rani E George; Takaomi Sanda; Megan Hanna; Stefan Fröhling; William Luther; Jianming Zhang; Yebin Ahn; Wenjun Zhou; Wendy B London; Patrick McGrady; Liquan Xue; Sergey Zozulya; Vlad E Gregor; Thomas R Webb; Nathanael S Gray; D Gary Gilliland; Lisa Diller; Heidi Greulich; Stephan W Morris; Matthew Meyerson; A Thomas Look
Journal:  Nature       Date:  2008-10-16       Impact factor: 49.962

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  2 in total

Review 1.  ALK inhibitors: a new targeted therapy in the treatment of advanced NSCLC.

Authors:  Francesca Casaluce; Assunta Sgambato; Paolo Maione; Antonio Rossi; Carmine Ferrara; Alba Napolitano; Giovanni Palazzolo; Fortunato Ciardiello; Cesare Gridelli
Journal:  Target Oncol       Date:  2013-01-17       Impact factor: 4.493

2.  ALK and NSCLC: Targeted therapy with ALK inhibitors.

Authors:  Bengt Hallberg; Ruth H Palmer
Journal:  F1000 Med Rep       Date:  2011-11-01
  2 in total

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