Expedient Access to 2‐Benzazepines by Palladium‐Catalyzed C−H Activation: Identification of a Unique Hsp90 Inhibitor Scaffold. Issue 62 (17th October 2018)

• Record Type: Journal Article
• Authors: Virelli, Matteo; Moroni, Elisabetta; Colombo, Giorgio; Fiengo, Lorenzo; Porta, Alessio; Ackermann, Lutz; Zanoni, Giuseppe
• Is Part Of: Chemistry. Volume 24:Issue 62(2018)
• Page Start: 16516
• Page End: 16520
• Publication Date: 2018-10-17
• Subjects: benzazepines -- C−H activation -- docking analysis -- Hsp90 -- inhibitors; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201804244
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Bioactive 2‐benzazepines were accessed in an atom‐ and step‐economical manner through a versatile palladium‐catalyzed C−H activation strategy. The C−H arylation required low catalyst loading and a mild base, which was reflected by a broad scope and high functional‐group tolerance. The benzotriazolodiazepinones were identified as new heat shock protein 90 (Hsp90) inhibiting lead compounds, with considerable potential for anti‐cancer applications. Abstract : Building with Pd : A new palladium‐catalyzed C−H activation strategy to access 2‐benzazepines in an atom‐ and step‐economical manner is reported. The C−H arylation featured low catalyst loading and a mild base, as reflected by a broad scope and high functional‐group tolerance. One of our benzotriazolodiazepinones was identified as a new heat shock protein 90 (Hsp90) nanomolar inhibitor, with potential for anti‐cancer applications.