Concise synthesis of E/F ring spiroethers from tigogenin. Carbaanalogs of steroidal sapogenins and their biological activity. Issue 224 (November 2022)

• Record Type: Journal Article
• Authors: Czajkowska-Szczykowska, Dorota; Olchowik-Grabarek, Ewa; Sękowski, Szymon; Żarkowski, Jacek; Morzycki, Jacek W.
• Is Part Of: Journal of steroid biochemistry and molecular biology. Issue 224(2022)
• Publication Date: 2022-11
• Subjects: DPH 1, 6-diphenyl-1, 3, 5-hexatriene -- TMA-DPH 1, 6-diphenyl-1, 3, 5-hexatriene-4′-trimethylammonium tosylate -- PBS phosphate buffered saline -- HSA human serum albumin -- DMPC 1, 2-dimyristoyl-sn-glycero-3-phosphocholine; Steroidal sapogenins -- Tigogenin -- Spiroethers -- Liposomes -- Antimicrobial activity -- Lipid order parameter; Steroid hormones -- Periodicals; Biochemistry -- Periodicals; Hormones -- Periodicals; Molecular Biology -- Periodicals; Hormones stéroïdes -- Périodiques; Steroid hormones; Periodicals; 572.579
• DOI: 10.1016/j.jsbmb.2022.106174
• Languages: English
• ISSNs: 0960-0760

Abstract

Abstract: A four-step synthesis of five- and six-membered E/F ring spiroethers from tigogenin has been developed. An efficient strategy that features bis-Grignard reaction of dinorcholanic lactone with appropriate bis(bromomagnesio)alkanes followed by acid-mediated spirocyclization was employed to construct a new class of steroid compounds having E and F ring junction as an oxa-carbacyclic system. The synthesized carbaanalogs interact with liposomes and albumin, and also exhibit antibacterial and antifungal activity, demonstrating their pharmacological potential. Graphical Abstract: A concise synthesis of steroidal sapogenin carbaanalogs ga1 Highlights: A simple synthesis of steroidal E/F ring spiroethers from dinorcholanic lactones. Biological activity of E/F ring spiroethers derived from tigogenin. Acid-catalyzed spirocyclization of diols.