Design and synthesis of novel xanthene derivatives

Miguel Maia; Andreia Palmeira; Diana Resende; Luis Gales; Madalena Pinto; Emília Sousa

doi:10.3390/ECMC2020-07504

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Design and synthesis of novel xanthene derivatives

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¹ Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
² Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, Portugal
³ Department of Molecular Biology, ICBAS - Instituto de Ciências Biomédicas Abel Salazar, University of Porto, Porto, Portugal
⁴ Bioengineering & Synthetic Microbiology, I3S – Instituto de Investigação e Inovação em Saúde, University of Porto, Porto, Portugal
⁵ Medicinal Chemistry: Drug Discovery and Drug Design, CIIMAR – Interdisciplinary Centre of Marine and Environmental Research, Faculty of Porto, Porto, Portugal.
⁶ Laboratory of Organic and Pharmaceutical Chemistry, FFUP – Faculty of Pharmacy, University of Porto, Porto, Portugal

Published: 06 November 2020 by MDPI in 6th International Electronic Conference on Medicinal Chemistry session General: Presentations

https://doi.org/10.3390/ECMC2020-07504

Abstract:

Xanthenes are a special class of oxygen-incorporating tricyclic compounds. Structurally related to xanthones, the presence of different substituents in position 9 presents a large impact on their physical and chemical properties, as well as their biological applications. Xanthene-9-carboxylic acid, 9-hydroxyxanthene (xanthydrol) and their respective derivatives have been reported to exhibit remarkable biological activities, namely neuroprotection, antidiabetic, cytotoxic, and antibacterial.

Herein, we report the design of a virtual library of 300 compounds whose pharmacokinetic properties were assessed through computational tools. Synthesis strategies to obtain such drug-like xanthene derivatives - amide coupling, reductive amination, aromatic halogenation and Suzuki coupling - are described. Azaxanthenes and thioxanthenes, important xanthene bioisosters, are also considered for their capacity to establish different biologic interactions for their influence pharmacokinetic properties. Future studies will include the investigation of their potential as bioactive compounds.

Keywords: drug design, synthesis, xanthene derivatives

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