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Article

α-Hydroxylactams as Efficient Entries to Diversely Functionalized Ferrociphenols: Synthesis and Antiproliferative Activity Studies

1
Chimie ParisTech, PSL, 11 rue Pierre et Marie Curie, F-75005 Paris, France
2
Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire (IPCM), 4 Place Jussieu, F-75005 Paris, France
3
Normandie University, URCOM, UNIHAVRE, FR3021, EA 3221, 25 rue P. Lebon BP 540, F-76058 Le Havre, France
*
Author to whom correspondence should be addressed.
Academic Editors: Chiara Brullo and Bruno Tasso
Molecules 2022, 27(14), 4549; https://doi.org/10.3390/molecules27144549
Received: 14 April 2022 / Revised: 12 July 2022 / Accepted: 12 July 2022 / Published: 16 July 2022
(This article belongs to the Special Issue Anticancer Compounds with Different Biological Targets)
The [ferrocene-ene-phenol] motif has been identified as the pharmacophore responsible for the anticancer activity of the family of ferrocene-based molecules coined ferrocifens, owing to its unique redox properties. The addition of imide entities to the historical ferrociphenol scaffold tremendously enhanced the cytotoxic activity of a large panel of cancer cell cultures and preliminary studies showed that the reduction of one of the carbonyl groups of the imide groups to the corresponding α-hydroxylactams only slightly affected the antiproliferative activity. As a continuation to these studies, we took advantage of the facile conversion of α-hydroxylactams to highly electrophilic N-acyliminium ions to graft various substituents to the imide motif of phthalimido ferrocidiphenol. Cell viability studies showed that the newly synthesized compounds showed diverse cytotoxic activities on two breast cancer cell lines, while only one compound was significantly less active on the non-tumorigenic cell line hTERT-RPE1. View Full-Text
Keywords: ferrocifen; hydroxylactam; N-acyliminium ion; anticancer activity; ferrocene ferrocifen; hydroxylactam; N-acyliminium ion; anticancer activity; ferrocene
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MDPI and ACS Style

Pigeon, P.; Gaschard, M.; Othman, M.; Salmain, M.; Jaouen, G. α-Hydroxylactams as Efficient Entries to Diversely Functionalized Ferrociphenols: Synthesis and Antiproliferative Activity Studies. Molecules 2022, 27, 4549. https://doi.org/10.3390/molecules27144549

AMA Style

Pigeon P, Gaschard M, Othman M, Salmain M, Jaouen G. α-Hydroxylactams as Efficient Entries to Diversely Functionalized Ferrociphenols: Synthesis and Antiproliferative Activity Studies. Molecules. 2022; 27(14):4549. https://doi.org/10.3390/molecules27144549

Chicago/Turabian Style

Pigeon, Pascal, Marie Gaschard, Mohamed Othman, Michèle Salmain, and Gérard Jaouen. 2022. "α-Hydroxylactams as Efficient Entries to Diversely Functionalized Ferrociphenols: Synthesis and Antiproliferative Activity Studies" Molecules 27, no. 14: 4549. https://doi.org/10.3390/molecules27144549

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