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Synthesis and cytotoxic effects on pancreatic cancer cells of resveratrol analogs

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Abstract

In this study, a series of resveratrol analogs was synthesized and the effects on the viability of pancreatic cancer cell lines were evaluated. The new molecules were designed by removing the 3- and 5-OH groups of resveratrol, and by incorporating other substituents in 4-position, or by replacing the dihydroxybenzene with other aromatic systems. In all compounds the 4′-OH was kept unalterated. The effects of the compounds on cell viability were analyzed in three pancreatic cancer cell lines with distinct genetic profiles. Several compounds (e.g., 5, 9, and 12) exhibited improved cytotoxic activities as compared to the reference compounds, making them potential candidates for further evaluation as anticancer drugs.

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Fig. 1
Scheme 1
Scheme 2
Fig. 2

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Abbreviations

RSV:

resveratrol

PC:

pancreatic cancer

SLB:

stilbene

4-HSLB:

4′-hydroxystilbene

TBSCl:

t-butyldimethylsilyl chloride

NEt3 :

triethylamine

TBAF:

tetra-n-butylammonium fluoride

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Acknowledgements

This study was supported by University “G. d’Annunzio” of Chieti local grants. The authors gratefully acknowledge Prof. Massimiliano Baldassarre of Institute of Medical Sciences, University of Aberdeen, for helpful comments and suggestions.

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Author notes

  1. These authors contributed equally: Barbara De Filippis, Laura De Lellis

Authors and Affiliations

  1. Unit of Medicinal Chemistry, Department of Pharmacy, University of Chieti “G. d’Annunzio”, Chieti, Italy

    Barbara De Filippis, Alessandra Ammazzalorso, Pasquale Amoia, Marialuigia Fantacuzzi, Letizia Giampietro, Cristina Maccallini & Rosa Amoroso

  2. Unit of General Pathology, Department of Pharmacy, University of Chieti “G. d’Annunzio”, Chieti, Italy

    Laura De Lellis, Rosalba Florio, Serena Veschi & Alessandro Cama

  3. Center on Aging Sciences and Translational Medicine (Ce.S.I.-MeT), University of Chieti “G. d’Annunzio”, Chieti, Italy

    Laura De Lellis, Rosalba Florio, Serena Veschi & Alessandro Cama

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  1. Barbara De Filippis
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Correspondence to Rosa Amoroso.

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De Filippis, B., De Lellis, L., Florio, R. et al. Synthesis and cytotoxic effects on pancreatic cancer cells of resveratrol analogs. Med Chem Res 28, 984–991 (2019). https://doi.org/10.1007/s00044-019-02351-3

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  • DOI: https://doi.org/10.1007/s00044-019-02351-3

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