This study explores the potential use of 1-(4-aminophenoxy)-3-(alkyl)propane-2-ol (anilines, 4) as building blocks for the preparation of membranogenic compounds. Anilines were synthesized via linear and convergent methods with good to high yields (39%-99%). Key intermediates, 1-(alkyloxy)-3-(4-nitrophenoxy)propan-2-ols (3), were obtained by reacting 2-(alkoxymethyl)oxirane (2) or 2-((4-nitrophenoxy)methyl)oxirane (7) with p-nitrophenol or an alcohol, respectively. Three reduction methods were employed to achieve the final anilines. Following chain-length screening, octyl and geranyl derivatives were selected to prepare lyso-phospholipid ether analogues. These compounds were then evaluated for their self-assembly properties in forming giant unilamellar vesicles using either phase transfer or electro-formation methodology.
1-(4-Aminophenoxy)-3-(alkyl)propane-2-ols as Building Blocks for the Preparation of Membranogenic Compounds
Amante C.;Di Martino M.;Romanini D.;Sardo C.;Sessa L.;Concilio S.;Piotto S.;
2025
Abstract
This study explores the potential use of 1-(4-aminophenoxy)-3-(alkyl)propane-2-ol (anilines, 4) as building blocks for the preparation of membranogenic compounds. Anilines were synthesized via linear and convergent methods with good to high yields (39%-99%). Key intermediates, 1-(alkyloxy)-3-(4-nitrophenoxy)propan-2-ols (3), were obtained by reacting 2-(alkoxymethyl)oxirane (2) or 2-((4-nitrophenoxy)methyl)oxirane (7) with p-nitrophenol or an alcohol, respectively. Three reduction methods were employed to achieve the final anilines. Following chain-length screening, octyl and geranyl derivatives were selected to prepare lyso-phospholipid ether analogues. These compounds were then evaluated for their self-assembly properties in forming giant unilamellar vesicles using either phase transfer or electro-formation methodology.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
