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Application of Stereocontrolled Stepwise [3+2] Cycloadditions to the Preparation of Inhibitors of α 4 β 1 ‐Integrin‐Mediated Hepatic Melanoma Metastasis

2005; Wiley; Volume: 44; Issue: 19 Linguagem: Inglês

10.1002/anie.200462497

1521-3773

Aizpea Zubia, Lorea Mendoza, Silvia Vivanco, Eneko Aldaba, Teresa Carrascal, Begoña Lecea, Ana Arrieta, Tahl Zimmerman, Fernando Vidal‐Vanaclocha, Fernando P. Cossío,

Biochemical and Structural Characterization

Angewandte Chemie International EditionVolume 44, Issue 19 p. 2903-2907 Communication Application of Stereocontrolled Stepwise [3+2] Cycloadditions to the Preparation of Inhibitors of α4β1-Integrin-Mediated Hepatic Melanoma Metastasis† Aizpea Zubia Dr., Aizpea Zubia Dr. Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this authorLorea Mendoza Dr., Lorea Mendoza Dr. Dominion Pharmakine, Ltd. Zamudio Technology Park, 48170 Zamudio, SpainSearch for more papers by this authorSilvia Vivanco Dr., Silvia Vivanco Dr. Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this authorEneko Aldaba, Eneko Aldaba Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this authorTeresa Carrascal Dr., Teresa Carrascal Dr. Dominion Pharmakine, Ltd. Zamudio Technology Park, 48170 Zamudio, SpainSearch for more papers by this authorBegoña Lecea Prof., Begoña Lecea Prof. Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this authorAna Arrieta Prof., Ana Arrieta Prof. Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this authorTahl Zimmerman, Tahl Zimmerman Centro Nacional de Investigaciones Oncológicas (CNIO), Structural and Computational Biology Programme, Melchor Fernández Almagro 3, 28029 Madrid, SpainSearch for more papers by this authorFernando Vidal-Vanaclocha Prof., Fernando Vidal-Vanaclocha Prof. Facultad de Medicina y Odontología-Medikuntza eta Odontologia Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, 48940 Lejona-Leioa, SpainSearch for more papers by this authorFernando P. Cossío Prof., Fernando P. Cossío Prof. fpcossio@sq.ehu.es Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this author Aizpea Zubia Dr., Aizpea Zubia Dr. Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this authorLorea Mendoza Dr., Lorea Mendoza Dr. Dominion Pharmakine, Ltd. Zamudio Technology Park, 48170 Zamudio, SpainSearch for more papers by this authorSilvia Vivanco Dr., Silvia Vivanco Dr. Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this authorEneko Aldaba, Eneko Aldaba Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this authorTeresa Carrascal Dr., Teresa Carrascal Dr. Dominion Pharmakine, Ltd. Zamudio Technology Park, 48170 Zamudio, SpainSearch for more papers by this authorBegoña Lecea Prof., Begoña Lecea Prof. Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this authorAna Arrieta Prof., Ana Arrieta Prof. Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this authorTahl Zimmerman, Tahl Zimmerman Centro Nacional de Investigaciones Oncológicas (CNIO), Structural and Computational Biology Programme, Melchor Fernández Almagro 3, 28029 Madrid, SpainSearch for more papers by this authorFernando Vidal-Vanaclocha Prof., Fernando Vidal-Vanaclocha Prof. Facultad de Medicina y Odontología-Medikuntza eta Odontologia Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, 48940 Lejona-Leioa, SpainSearch for more papers by this authorFernando P. Cossío Prof., Fernando P. Cossío Prof. fpcossio@sq.ehu.es Facultad de Química-Kimika Fakultatea, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P. O. Box 1072, 20080 San Sebastián-Donostia, Spain, Fax: (+34) 943-212-236Search for more papers by this author First published: 03 May 2005 https://doi.org/10.1002/anie.200462497Citations: 54 † This work was supported by the Universidad del País Vasco-Euskal Herriko Unibertsitatea, Gobierno Vasco-Eusko Jaurlaritza (grants 9/UPV00170.215-13548/2001 and -13641/2001), Dominion Pharmakine Ltd., and by the Spanish Ministerio de Educación y Ciencia (grants BQU2001-0904, BIO2003-02246, and SAF99-0042). A.Z. and E.A. are recipients of fellowships from the GV-EJ. We thank Dr. Francisco J. Blanco and Dr. Pascal García (CNIO, Spain) for their advice on the 15N–1H HSQC experiments. We also thank Dr. Antonio Llamas (Unidade de Raios X, Universidade de Santiago de Compostela, Spain) for the X-ray diffraction analysis of compound 11 d. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract Inhibitors of the interaction between protein VLA-4 and its natural ligand VCAM-1 have been designed, even though the structure of the protein remains unresolved. The rational design relied on the simulation of the steric and electronic properties of the active loop of VCAM-1, whose structure is known (see picture), and the inhibitors were readily prepared by stereoselective stepwise [3+2] cycloadditions. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z462497_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume44, Issue19May 6, 2005Pages 2903-2907 RelatedInformation