Literature DB >> 10560734

An efficient synthesis of a 4'-phosphonodifluoromethyl-3'-formyl-phenylalanine containing SRC SH2 ligand.

W C Shakespeare1, R S Bohacek, S S Narula, M D Azimioara, R W Yuan, D C Dalgarno, L Madden, M C Botfield, D A Holt.   

Abstract

A CuBr-mediated, regioselective cross-coupling between methyl 2,5-diiodobenzoate (4) and [(diethoxyphosphinyl)difluoromethyl]zinc bromide is reported. Palladium-catalyzed incorporation of an amino acid side chain, followed by subsequent modifications resulted in the rapid construction of 2. Compound 2 was designed to engage Cys188 of the Src SH2 domain, however, this was not observed spectroscopically.

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Year:  1999        PMID: 10560734     DOI: 10.1016/s0960-894x(99)00545-4

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  1 in total

1.  Structure-based design of an osteoclast-selective, nonpeptide src homology 2 inhibitor with in vivo antiresorptive activity.

Authors:  W Shakespeare; M Yang; R Bohacek; F Cerasoli; K Stebbins; R Sundaramoorthi; M Azimioara; C Vu; S Pradeepan; C Metcalf; C Haraldson; T Merry; D Dalgarno; S Narula; M Hatada; X Lu; M R van Schravendijk; S Adams; S Violette; J Smith; W Guan; C Bartlett; J Herson; J Iuliucci; M Weigele; T Sawyer
Journal:  Proc Natl Acad Sci U S A       Date:  2000-08-15       Impact factor: 11.205

  1 in total

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