The previously neglected "angular" spirocyclic azetidines have been synthesized, characterized, and validated in drug discovery. We have shown that these compounds could act as bioisosteres for common saturated six-membered heterocycles. Their incorporation into the structure of the anticancer drug Sonidegib (instead of morpholine), and Danofloxacine (instead of piperazine) provided novel patent-free analogs with similar physicochemical properties and high activity.
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"Angular" Spirocyclic Azetidines: Synthesis, Characterization, and Evaluation in Drug Discovery.
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Enamine Ltd, Winston Churchill st. 78, 02094, Kyiv, Ukraine.
The previously neglected "angular" spirocyclic azetidines have been synthesized, characterized, and validated in drug discovery. We have shown that these compounds could act as bioisosteres for common saturated six-membered heterocycles. Their incorporation into the structure of the anticancer drug Sonidegib (instead of morpholine), and Danofloxacine (instead of piperazine) provided novel patent-free analogs with similar physicochemical properties and high activity.
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Eleven conjoined coumarins possessing a chromeno[3,4-]chromene-6,7-dione skeleton have been synthesized via the reaction of electron-rich phenols with esters of coumarin-3-carboxylic acids, catalyzed by either Lewis acids or 4-dimethylaminopyridine. Furthermore, Michael-type addition to angular benzo[]coumarins is possible, leading to conjugated helical systems. Arrangement of the electron-donating amino groups at diverse positions on this heterocyclic skeleton makes it possible to obtain π-expanded coumarins with emission either sensitive to, or entirely independent of, solvent polarity with large Stokes shifts.
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Department of Chemistry, University of Rochester, 120 Trustee Road, Rochester, New York 14611, United States.
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Department of Chemistry, Dalhousie University, P. O. Box 15000, Halifax, Nova Scotia, Canada B3H 4R2.
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Laboratorium für Organische Chemie, ETH Zürich, CH-8093 Zürich, Switzerland.
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