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An alternative approach to the synthesis of anticancer molecule spirobrassinin and its 2′-amino analogues

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Abstract

A convenient synthesis of the cruciferous phytoalexin (S)-(−)-spirobrassinin and its (±)-2′-amino analogues have been achieved. Our synthetic route towards (S)-(−)-spirobrassinin is based on the CrO3-mediated cyclization of chiral 1-(2′,3′,4′,6′-tetra-O-acetyl-ß-D-glucopyranosyl)brassinin and subsequent removal of the chiral auxiliary. (±)-2′-Amino analogues of spirobrassinin and 1-methoxyspirobrassinin were obtained from thioureas in one step in an efficient manner with the aid of CrO3. New synthesized compounds were screened in vitro for antiproliferative/cytotoxic activity against six human cancer cell lines by MTT assay. Amino analogues with CF3 functionality displayed good antiproliferative effect.

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Acknowledgments

The present study was supported in part by the Grant Agency of Ministry of the Education, Science, Research and Sport of the Slovak Republic (VEGA 1/0753/17 and VEGA 1/0018/16), and the Slovak Research and Development Agency under the Contract No. APVV-16-0446. Moreover, this publication is the result of the project implementation: „Medicínsky univerzitný vedecký park v Košiciach (MediPark, Košice - Fáza II.)“, kód ITMS2014+313011D103 supported by the Operational Programme Research & Innovation, funded by the ERDF“. The authors thank Assoc. prof. D. Berkeš and Dr. J. Markus for synthesis and providing of the (R)-2-(1H-indol-3-yl)glycine.

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Authors and Affiliations

  1. Department of Organic Chemistry, Institute of Chemical Sciences, Faculty of Science, P.J. Šafárik University, Moyzesova 11, 040 01, Kosice, Slovak Republic

    Mariana Budovská

  2. Department of Pharmacology, Faculty of Medicine, P.J. Šafárik University, SNP 1, 040 11, Kosice, Slovak Republic

    Viera Tischlerová & Ján Mojžiš

  3. Department of Analytical Chemistry, Institute of Chemical Sciences, Faculty of Science, P. J. Šafárik University, Moyzesova 11, 040 01, Kosice, Slovak Republic

    Oleksandr Kozlov & Taťána Gondová

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  1. Mariana Budovská
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  2. Viera Tischlerová
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  3. Ján Mojžiš
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  4. Oleksandr Kozlov
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  5. Taťána Gondová
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Correspondence to Mariana Budovská.

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Budovská, M., Tischlerová, V., Mojžiš, J. et al. An alternative approach to the synthesis of anticancer molecule spirobrassinin and its 2′-amino analogues. Monatsh Chem 151, 63–77 (2020). https://doi.org/10.1007/s00706-019-02528-x

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  • DOI: https://doi.org/10.1007/s00706-019-02528-x

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