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1.
Structure-based design of novel bicyclic nonpeptide inhibitors for the src SH2 domain.
Shakespeare, W C; Bohacek, R S; Azimioara, M D; Macek, K J; Luke, G P; Dalgarno, D C; Hatada, M H; Lu, X; Violette, S M; Bartlett, C; Sawyer, T K.
J Med Chem ; 43(21): 3815-9, 2000 Oct 19.
Article in English | MEDLINE | ID: mdl-11052784

Subject(s)
Bridged Bicyclo Compounds/chemical synthesis , src Homology Domains , Bridged Bicyclo Compounds/chemistry , Crystallography, X-Ray , Drug Design , Fluorescence Polarization , Models, Molecular , Structure-Activity Relationship
2.
An efficient synthesis of a 4'-phosphonodifluoromethyl-3'-formyl-phenylalanine containing SRC SH2 ligand.
Shakespeare, W C; Bohacek, R S; Narula, S S; Azimioara, M D; Yuan, R W; Dalgarno, D C; Madden, L; Botfield, M C; Holt, D A.
Bioorg Med Chem Lett ; 9(21): 3109-12, 1999 Nov 01.
Article in English | MEDLINE | ID: mdl-10560734

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.


Subject(s)
Fluorine Compounds/chemical synthesis , Organophosphonates/chemical synthesis , Phenylalanine/analogs & derivatives , src Homology Domains , Binding Sites , Cysteine/chemistry , Fluorine Compounds/pharmacology , Ligands , Molecular Structure , Organophosphonates/pharmacology , Protein Binding , Protein-Tyrosine Kinases/chemistry
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