Unprecedented Synthesis of a Terminal Dialkynyl Primary Carbinamine: A Bioinspired Lipid With Cytotoxic Activities

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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).