Bioactive cyclometalated phthalimides: design, synthesis and kinase inhibition was written by Blanck, Sebastian;Geisselbrecht, Yann;Kraeling, Katja;Middel, Stephen;Mietke, Thomas;Harms, Klaus;Essen, Lars-Oliver;Meggers, Eric. And the article was included in Dalton Transactions in 2012.Synthetic Route of C15H10BrNO2 The following contents are mentioned in the article:
The regioselective cyclometalation of 4-(pyridin-2-yl)phthalimide was exploited for the economical design of organometallic protein kinase inhibitors. 4-(Pyridin-2-yl)phthalimide can be prepared from inexpensive 4-bromophthalimide in just three steps including one Pd-catalyzed Stille cross-coupling. The versatility of this new ligand was demonstrated with the synthesis of ruthenium(II) half-sandwich as well as octahedral ruthenium(II) and iridium(III) complexes. The regioselectivity of the C-H activation in the course of the cyclometalation can be influenced by the reaction conditions and the steric demand of the introduced metal complex fragment. The biol. activity of this new class of metalated phthalimides was evaluated by profiling two representative members against a large panel of human protein kinases. A cocrystal structure of one metallo-phthalimide with the protein kinase Pim1 confirmed an ATP-competitive binding with the intended hydrogen bonding between the phthalimide moiety and the hinge region of the ATP-binding site. This study involved multiple reactions and reactants, such as 2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1Synthetic Route of C15H10BrNO2).
2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Synthetic Route of C15H10BrNO2
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Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles