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Application of organocatalysis in bioorganometallic chemistry: asymmetric synthesis of multifunctionalized spirocyclic pyrazolone–ferrocene hybrids as novel RalA inhibitors

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Abstract

We have designed and synthesized a collection of chiral spirocyclic pyrazolone–ferrocene organometallic hybrids bearing multiple stereocenters and functional groups via organocatalysis. Compound 5b in this library displayed potent RalA inhibition, and it led to accumulation of reactive oxygen species and inhibited proliferation of pancreatic cancer cells. Molecular docking studies of 5b onto the RalA allosteric site suggest that it binds similarly to a C3 exoenzyme substrate peptide. This an efficient application of asymmetric organocatalysis in organometallic medicinal chemistry.

Graphical abstract: Application of organocatalysis in bioorganometallic chemistry: asymmetric synthesis of multifunctionalized spirocyclic pyrazolone–ferrocene hybrids as novel RalA inhibitors

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Publication details

The article was received on 26 Apr 2018, accepted on 11 Jun 2018 and first published on 11 Jun 2018


Article type: Research Article
DOI: 10.1039/C8QO00422F
Citation: Org. Chem. Front., 2018, Advance Article
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    Application of organocatalysis in bioorganometallic chemistry: asymmetric synthesis of multifunctionalized spirocyclic pyrazolone–ferrocene hybrids as novel RalA inhibitors

    Y. Zhang, C. Wang, W. Huang, P. Haruehanroengra, C. Peng, J. Sheng, B. Han and G. He, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00422F

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