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Article

Synthesis and Biological Screening of Structurally Modified Phaeosphaeride Analogues

Department of Chemistry, Aristotle University of Thessaloniki, University Campus, 54124 Thessaloniki, Greece
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Author to whom correspondence should be addressed.
Molecules 2025, 30(9), 2016; https://doi.org/10.3390/molecules30092016
Submission received: 26 March 2025 / Revised: 25 April 2025 / Accepted: 30 April 2025 / Published: 30 April 2025
(This article belongs to the Section Medicinal Chemistry)

Abstract

Phaeosphaeride A and its analogues have been extensively explored for their potential pharmacological applications, particularly in the development of anticancer agents. In this study, the synthesis of structurally modified phaeosphaeride analogues is reported. The structures of the synthesized analogues bearing the tetrahydro- and hexahydro-2H-furo[3,2-b]pyran-2-one and hexahydropyrano[3,2-b]pyrrol-2(1H)-one moieties were assessed and the new compounds were evaluated for their antiproliferative activity against two cancer cell lines. Despite successful synthesis and structural modification, the majority of the phaeosphaeride analogues exhibited limited bioactivity. Structure-activity relationship studies suggested that specific modifications did not enhance anticancer potency. The hydroxy groups and the alkyl moiety in cyclic or non-cyclic phaeosphaeride analogues contribute to the activity, as shown by the activity of compounds 24 and 25. The presence of double bonds and oxygen or nitrogen heteroatoms in furopyranones or pyranopyrrolones 9, 28, 29 and 33a, does not significantly impact cytotoxic activity. These findings highlight the challenges in optimizing phaeosphaerides for anticancer applications and provide insights into future structural modifications to improve their therapeutic potential. Moreover, our studies open a synthetic route for the development of new phaeosphaeride analogues.
Keywords: phaeosphaeride; tetronate; tetramate; natural product analogues; anticancer phaeosphaeride; tetronate; tetramate; natural product analogues; anticancer

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MDPI and ACS Style

Rantzios, K.; Chatzimentor, O.-E.; Leonidis, G.; Giuliani, J.; Sigala, I.; Sarli, V. Synthesis and Biological Screening of Structurally Modified Phaeosphaeride Analogues. Molecules 2025, 30, 2016. https://doi.org/10.3390/molecules30092016

AMA Style

Rantzios K, Chatzimentor O-E, Leonidis G, Giuliani J, Sigala I, Sarli V. Synthesis and Biological Screening of Structurally Modified Phaeosphaeride Analogues. Molecules. 2025; 30(9):2016. https://doi.org/10.3390/molecules30092016

Chicago/Turabian Style

Rantzios, Konstantinos, Oraia-Eirini Chatzimentor, George Leonidis, Jorgo Giuliani, Ioanna Sigala, and Vasiliki Sarli. 2025. "Synthesis and Biological Screening of Structurally Modified Phaeosphaeride Analogues" Molecules 30, no. 9: 2016. https://doi.org/10.3390/molecules30092016

APA Style

Rantzios, K., Chatzimentor, O.-E., Leonidis, G., Giuliani, J., Sigala, I., & Sarli, V. (2025). Synthesis and Biological Screening of Structurally Modified Phaeosphaeride Analogues. Molecules, 30(9), 2016. https://doi.org/10.3390/molecules30092016

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