Chromenopyrrole derivatives with multiple stereocenters and variable ring fusion pattern are found in many natural products and biologically appealing molecules. By employing a build/couple/pair strategy, we have recently reported on the discovery of a serendipitous cascade to access a diverse collection of chromenopyrroles. This protocol features a one-pot cascade that includes the generation of azomethine ylide and intramolecular [3 + 2]-cycloaddition. Phenotypic screening of the developed pilot library enabled the identification of chemical probes that efficiently suppress mitochondrial membrane potential, elevate reactive oxygen species content, and deplete ATP content in a hepatoma cell line (Hepa1-6), without affecting the proliferation of T- or B-cells. This selective targeting represents a new approach for the treatment of cancer. [Figure not available: see fulltext.]

Schilf P., Srinivasulu V., Bolognesi M.L., Ibrahim S., Majdalawieh A.F., Abu-Yousef I.A., et al. (2021). Design and synthesis of nature-inspired chromenopyrroles as potential modulators of mitochondrial metabolism. MEDICINAL CHEMISTRY RESEARCH, 30(3), 635-646 [10.1007/s00044-020-02669-3].

Design and synthesis of nature-inspired chromenopyrroles as potential modulators of mitochondrial metabolism

Bolognesi M. L.;
2021

Abstract

Chromenopyrrole derivatives with multiple stereocenters and variable ring fusion pattern are found in many natural products and biologically appealing molecules. By employing a build/couple/pair strategy, we have recently reported on the discovery of a serendipitous cascade to access a diverse collection of chromenopyrroles. This protocol features a one-pot cascade that includes the generation of azomethine ylide and intramolecular [3 + 2]-cycloaddition. Phenotypic screening of the developed pilot library enabled the identification of chemical probes that efficiently suppress mitochondrial membrane potential, elevate reactive oxygen species content, and deplete ATP content in a hepatoma cell line (Hepa1-6), without affecting the proliferation of T- or B-cells. This selective targeting represents a new approach for the treatment of cancer. [Figure not available: see fulltext.]
2021
Schilf P., Srinivasulu V., Bolognesi M.L., Ibrahim S., Majdalawieh A.F., Abu-Yousef I.A., et al. (2021). Design and synthesis of nature-inspired chromenopyrroles as potential modulators of mitochondrial metabolism. MEDICINAL CHEMISTRY RESEARCH, 30(3), 635-646 [10.1007/s00044-020-02669-3].
Schilf P.; Srinivasulu V.; Bolognesi M.L.; Ibrahim S.; Majdalawieh A.F.; Abu-Yousef I.A.; Omar H.A.; ElAwady R.; Al-Tel T.H.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/843455
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