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      Synthesis of substituted indenones and indanones by a Suzuki–Miyaura coupling/acid-promoted cyclisation sequence

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          Abstract

          A one-pot Suzuki-Miyaura cross-coupling/acid-catalyzed cyclisation leading to indenones and indanones in modest to good yields is reported.

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          Most cited references31

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          Rhodium/Copper-Catalyzed Annulation of Benzimides with Internal Alkynes: Indenone Synthesis through Sequential CH and CN Cleavage

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            Synthesis and structure-activity relationships of acetylcholinesterase inhibitors: 1-benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine hydrochloride and related compounds.

            Following the discovery of a new series of anti-acetylcholinesterase (anti-AChE) inhibitors such as 1-benzyl-4-[2-(N-benzoylamino)ethyl]piperidine (1), we reported that its rigid analogue, 1-benzyl-4-(2-isoindolin-2-ylethyl)piperidine (5), had more potent activity. We have extended the structure-activity relationship (SAR) study for the rigid analogue and found that the 2-isoindoline moiety in compound 5 can be replaced with a indanone moiety (8) without a major loss in potency. Among the indanone derivatives, 1-benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine (13e) (E2020) (IC50 = 5.7 nM) was found to be one of the most potent anti-AChE inhibitors. Compound 13e showed a selective affinity 1250 times greater for AChE than for butyrylcholinesterase. In vivo studies demonstrated that 13e has a longer duration of action than physostigmine at a dose of 5 mg/kg (po) and produced a marked and significant increase in acetylcholine content in rat cerebral cortex. We report the synthesis, SAR, and a proposed hypothetical binding site of 13e (E2020).
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              Cobalt-catalyzed arylation of aldimines via directed C–H bond functionalization: addition of 2-arylpyridines and self-coupling of aromatic aldimines

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                Author and article information

                Journal
                OBCRAK
                Org. Biomol. Chem.
                Org. Biomol. Chem.
                Royal Society of Chemistry (RSC)
                1477-0520
                1477-0539
                2014
                2014
                : 12
                : 5
                : 728-731
                Article
                10.1039/C3OB41974F
                24323234
                d398121f-9271-4252-b759-0e34d097cfef
                © 2014
                History

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