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      Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

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          Summary

          Oxindole scaffolds are prevalent in natural products and have been recognized as privileged substructures in new drug discovery. Several oxindole-containing compounds have advanced into clinical trials for the treatment of different diseases. Among these compounds, enantioenriched 3-hydroxyoxindole scaffolds also exist in natural products and have proven to possess promising biological activities. A large number of catalytic asymmetric strategies toward the construction of 3-hydroxyoxindoles based on transition metal catalysis and organocatalysis have been reported in the last decades. Additionally, 3-hydroxyoxindoles as versatile precursors have also been used in the total synthesis of natural products and for constructing structurally novel scaffolds. In this review, we aim to provide an overview about the catalytic asymmetric synthesis of biologically important 3-substituted 3-hydroxyoxindoles and 3-hydroxyoxindole-based further transformations.

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          C-H bond activation enables the rapid construction and late-stage diversification of functional molecules.

          Joanna Wencel-Delord, Frank Glorius (2013)
          The beginning of the twenty-first century has witnessed significant advances in the field of C-H bond activation, and this transformation is now an established piece in the synthetic chemists' toolbox. This methodology has the potential to be used in many different areas of chemistry, for example it provides a perfect opportunity for the late-stage diversification of various kinds of organic scaffolds, ranging from relatively small molecules like drug candidates, to complex polydisperse organic compounds such as polymers. In this way, C-H activation approaches enable relatively straightforward access to a plethora of analogues or can help to streamline the lead-optimization phase. Furthermore, synthetic pathways for the construction of complex organic materials can now be designed that are more atom- and step-economical than previous methods and, in some cases, can be based on synthetic disconnections that are just not possible without C-H activation. This Perspective highlights the potential of metal-catalysed C-H bond activation reactions, which now extend beyond the field of traditional synthetic organic chemistry.
          Article 0 comments Cited 510 times – based on 0 reviews     Review now
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            Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

            Chris V Galliford, Karl A. Scheidt (2007)
            The 3,3'-pyrrolidinyl-spirooxindole unit is a privileged heterocyclic motif that forms the core of a large family of alkaloid natural products with strong bioactivity profiles and interesting structural properties. Significant recent advances in the synthesis of this fused heterocyclic system have led to intense interest in the development of related compounds as potential medicinal agents or biological probes.
            Article 0 comments Cited 334 times – based on 0 reviews     Review now
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              Small molecule selected to disrupt oncogenic protein EWS-FLI1 interaction with RNA Helicase A inhibits Ewing's Sarcoma

              Hayriye Erkizan, Yali Kong, Melinda Merchant … (2009)
              Many sarcomas and leukemias carry non-random chromosomal translocations encoding mutant fusion transcription factors that are essential to their molecular pathogenesis. These novel, tumor-specific proteins provides a unique opportunity for the development of highly selective anticancer drugs that has yet to be exploited. A particularly clear example is provided by Ewing's Sarcoma Family Tumors (ESFT) which contain a characteristic t(11;22) translocation leading to expression of the oncogenic fusion protein EWS-FLI1. EWS-FLI1 is a disordered protein that precluded standard structure-based small molecule inhibitor design. Using surface plasmon resonance screening, we discovered a lead compound, NSC635437. A derivative compound, YK-4-279, blocks RHA binding to EWS-FLI1, induces apoptosis in ESFT cells, and reduces the growth of ESFT orthotopic xenografts. These findings provide proof of principle that inhibiting the interaction of mutant cancer-specific transcription factors with the normal cellular binding partners required for their oncogenic activity provides a promising strategy for the development of uniquely effective, tumor-specific anticancer agents.
              Article 0 comments Cited 150 times – based on 0 reviews     Review now
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                Author and article information

                Contributors
                De-Quan Yu
                Hong-Min Liu
                Tehshik P Yoon: Role: Associate Editor
                Journal
                Journal ID (nlm-ta): Beilstein J Org Chem
                Journal ID (iso-abbrev): Beilstein J Org Chem
                Title: Beilstein Journal of Organic Chemistry
                Publisher: Beilstein-Institut (Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany )
                ISSN (Electronic): 1860-5397
                Publication date Collection: 2016
                Publication date (Electronic): 18 May 2016
                Volume: 12
                Pages: 1000-1039
                Affiliations
                [1 ]School of Pharmaceutical Sciences & Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou University, Zhengzhou 450001, China
                [2 ]School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Queensland, Australia
                Article
                DOI: 10.3762/bjoc.12.98
                PMC ID: 4902056
                PubMed ID: 27340490
                SO-VID: 73b88f65-a2a4-457d-90e5-3a23eb59038b
                Copyright © Copyright © 2016, Yu et al; licensee Beilstein-Institut.
                License:

                This is an Open Access article under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( http://www.beilstein-journals.org/bjoc)

                History
                Date received : 28 January 2016
                Date accepted : 30 April 2016
                Categories
                Subject: Review
                Subject: Chemistry
                Subject: Organic Chemistry

                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: 3-hydroxyoxindoles,oxindoles,organocatalysis,spirooxindoles,transition metal catalysis
                Data availability:
                ScienceOpen disciplines: Organic & Biomolecular chemistry
                Keywords: 3-hydroxyoxindoles, oxindoles, organocatalysis, spirooxindoles, transition metal catalysis

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