Unprecedented Synthesis of a Terminal Dialkynyl Primary Carbinamine: A Bioinspired Lipid With Cytotoxic Activities
Year: 2026
Type: article
Abstract: 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).
Source: ChemistrySelect
DOI: 10.1002/slct.73742
Institutions: Centre National de la Recherche Scientifique, Laboratoire de Chimie de Coordination, Laboratoire des Agroressources, Biomolécules et Chimie pour l’Innovation en Santé, Université de Toulouse, Université de Limoges, Université Mohammed VI Polytechnique, Institut de Pharmacologie et de Biologie Structurale, Synthèse et Physicochimie de Molécules d'Intérêt Biologique
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $3,880
Funder: Agence Nationale de la Recherche
OpenAlex ID: W7168047345