A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides. Issue 68 (7th November 2019)

• Record Type: Journal Article
• Authors: Zimmermann, Stefan; Akbarzadeh, Mohammad; Otte, Felix; Strohmann, Carsten; Sankar, Muthukumar Gomathi; Ziegler, Slava; Pahl, Axel; Sievers, Sonja; Kumar, Kamal
• Is Part Of: Chemistry. Volume 25:Issue 68(2019)
• Page Start: 15498
• Page End: 15503
• Publication Date: 2019-11-07
• Subjects: branching pathway -- cell painting -- folding pathway -- mitotic inhibitors -- sulfonamides; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201904175
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A "branching–folding" synthetic strategy that affords a range of diverse cyclic benzo‐sulfonamide scaffolds is presented. Whereas different annulation reactions on common ketimine substrates build the branching phase of the scaffold synthesis, a common hydrogenative ring‐expansion method, facilitated by an increase of the ring‐strain during the branching phase, led to sulfonamides bearing medium‐sized rings in a folding pathway. Cell painting assay was successfully employed to identify tubulin targeting sulfonamides as novel mitotic inhibitors. Abstract : Branch, fold and paint ! A "branching–folding" synthetic strategy delivers a range of diverse cyclic benzo‐sulfonamides and a cell painting analysis led to disclose novel tubulin targeting sulfonamide mitotic inhibitors.