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Fuertes M, Selas A, Trejo A, et al. Synthesis of Hybrid Phosphorated Indenoquinolines and Biological Evaluation as Topoisomerase I Inhibitors and Antiproliferative agents. Bioorg Med Chem Lett. 2021;128517doi: 10.1016/j.bmcl.2021.128517.
Fuertes, M., Selas, A., Trejo, A., Knudsen, B. R., Palacios, F., & Alonso, C. (2021). Synthesis of Hybrid Phosphorated Indenoquinolines and Biological Evaluation as Topoisomerase I Inhibitors and Antiproliferative agents. Bioorganic & medicinal chemistry letters, 128517. https://doi.org/10.1016/j.bmcl.2021.128517
Fuertes, María, et al. "Synthesis of Hybrid Phosphorated Indenoquinolines and Biological Evaluation as Topoisomerase I Inhibitors and Antiproliferative agents." Bioorganic & medicinal chemistry letters vol. (2021): 128517. doi: https://doi.org/10.1016/j.bmcl.2021.128517
Fuertes M, Selas A, Trejo A, Knudsen BR, Palacios F, Alonso C. Synthesis of Hybrid Phosphorated Indenoquinolines and Biological Evaluation as Topoisomerase I Inhibitors and Antiproliferative agents. Bioorg Med Chem Lett. 2021 Dec 21;128517. doi: 10.1016/j.bmcl.2021.128517. Epub 2021 Dec 21. PMID: 34952177.
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Bioorg Med Chem Lett. 2021 Dec 21;128517. doi: 10.1016/j.bmcl.2021.128517. Epub 2021 Dec 21.

Synthesis of Hybrid Phosphorated Indenoquinolines and Biological Evaluation as Topoisomerase I Inhibitors and Antiproliferative agents.

Bioorganic & medicinal chemistry letters

María Fuertes, Asier Selas, Angela Trejo, Birgitta R Knudsen, Francisco Palacios, Concepción Alonso

Affiliations

  1. Departamento de Química Orgánica I, Facultad de Farmacia and Centro de Investigación Lascaray (Lascaray Research Center). Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU). Paseo de la Universidad 7, 01006 Vitoria-Gasteiz, Spain.
  2. Department of Molecular Biology and Genetics and Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Aarhus 8000, Denmark.

PMID: 34952177 DOI: 10.1016/j.bmcl.2021.128517

Abstract

This work describes the first synthesis of diethyl 6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinolinylphosphonates 5, diethyl 7H-indeno[2,1-c]quinolinylphosphonates 6 and diethyl 7-oxo-7H-indeno[2,1-c]quinolinylphosphonates 7, which were prepared in good to high overall yields. The synthetic route involves a multicomponent reaction of 2-phosphonateaniline, aldehydes and indene as olefin and allows the selective generation of three stereogenic centres in a short, efficient and reliable manner. The selective dehydrogenation of 1,2,3,4-tetrahydroindenoquinolines leads to the formation of corresponding indenoquinolines, and subsequent oxidation of methylene group of the indenoquinolines allows the access to indenoquinolinones.

Copyright © 2021. Published by Elsevier Ltd.

Keywords: Antiproliferative effect; Enzyme inhibition; Indenoquinolinyl phosphonates; Topoisomerase I

Conflict of interest statement

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this pa

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