Bioorganic & Medicinal Chemistry Letters · 1998 · 19 citations · 27 references
PharmacyMedicinal ChemistryPharmacologyDrug DiscoveryStructure-activity RelationshipsSynthetic Medicinal ChemistryAmino Acid Biosynthesis InhibitionEnzyme InhibitionStructure-activity Relationship AnalysisBiological Activity FeaturesOne-pot Heterocycle SynthesisSubstituent Effects On Biological ActivityTyrosine BiosynthesisTyrosine OxidationTyrosine-targeted Inhibitors
A didemnin B analog containing a Tic (1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) as a conformationally restrained replacement for tyrosine has been synthesized and shown to have comparable potency as a protein biosynthesis inhibitor. Synthetic highlights include an oxidation of an alcohol to an acid in the presence of the sensitive Tic heterocycle and a modified Schmidt-type one-pot macrocyclization.
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B. Lindgren, Torsten Nilsson, Steinar Husebye et al. · Acta chemica Scandinavica/Acta chemica Scandinavica. B, Organic chemistry and biochemistry/Acta chemica Scandinavica. A, Physical and inorganic chemistry/Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry/Acta chemica Scandinavica. Series A, Physical and inorganic chemistry · 1973 · 506 citations · Full text
Structure−Activity Relationships of the Didemnins
Ryuichi Sakai, Kenneth L. Rinehart, Vimal Kishore et al. · Journal of Medicinal Chemistry · 1996 · 151 citations