Unprecedented Synthesis of a Terminal Dialkynyl Primary Carbinamine: A Bioinspired Lipid With Cytotoxic Activities
Abstract
This study reports the unprecedented synthesis of a bioinspired compound incorporating a terminal dialkynyl primary carbinamine moiety, which represents a bioisostere of the antitumor lipidic dialkynyl carbinol pharmacophore. After exploring several synthetic routes, the target compound, isolated as its hydrochloride salt, is successfully obtained via a key N -Boc ynaldimine intermediate, generated from the pentadec-2-ynal in four steps. Additionally, three terminal dialkynyl secondary carbinamines are described. Among the novel compounds prepared in this work, the nonnatural lipidic terminal dialkynyl primary carbinamine exhibits the highest cytotoxicity, demonstrating promising activities against three different cancer cell lines (IC 50 ranging from 2 to 5 µM).
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BibTeX
@article{toublet2026unprecedented,
title = {{Unprecedented Synthesis of a Terminal Dialkynyl Primary Carbinamine: A Bioinspired Lipid With Cytotoxic Activities}},
author = {François‐xavier Toublet and Abdelhak Lachguar and Mohamed Salem and Bastien Dumais and Sébastien Britton and Nadège Preuilh and Stéphanie Ballereau and Yves Génisson and Valérie Maraval and Vania Bernardes-Génisson},
journal = {ChemistrySelect},
year = {2026},
month = sep,
doi = {10.1002/slct.73742},
url = {https://hal.science/hal-05745791v1},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Unprecedented Synthesis of a Terminal Dialkynyl Primary Carbinamine: A Bioinspired Lipid With Cytotoxic Activities
AU - François‐xavier Toublet
AU - Abdelhak Lachguar
AU - Mohamed Salem
AU - Bastien Dumais
AU - Sébastien Britton
AU - Nadège Preuilh
AU - Stéphanie Ballereau
AU - Yves Génisson
AU - Valérie Maraval
AU - Vania Bernardes-Génisson
PY - 2026
DA - 2026/09/10
JO - ChemistrySelect
DO - 10.1002/slct.73742
UR - https://hal.science/hal-05745791v1
AB - This study reports the unprecedented synthesis of a bioinspired compound incorporating a terminal dialkynyl primary carbinamine moiety, which represents a bioisostere of the antitumor lipidic dialkynyl carbinol pharmacophore. After exploring several synthetic routes, the target compound, isolated as its hydrochloride salt, is successfully obtained via a key N -Boc ynaldimine intermediate, generated from the pentadec-2-ynal in four steps. Additionally, three terminal dialkynyl secondary carbinamines are described. Among the novel compounds prepared in this work, the nonnatural lipidic terminal dialkynyl primary carbinamine exhibits the highest cytotoxicity, demonstrating promising activities against three different cancer cell lines (IC 50 ranging from 2 to 5 µM).
SN - 2365-6549
SN - 2365-6549
ER -