Bis-alkylation of a pteroic acid photosensitizer: Synthesis, structural characterization, and theoretical studies

JOSÉ L. FONSECA CASTRO; SOSA, MARÍA JOSÉ; PETROSELLI GABRIELA; ERRA BALSELLS ROSA; QUINDT, MATÍAS I.; GREER, ALEXANDER; GREER, EDYTA M.; BONESI, SERGIO M.; THOMAS ANDRÉS H.; VIGNONI MARIANA

Chicago

Conferencia; American Chemistry Society (ACS) Fall 2022; 2022

American Chemistry Society

A bis-decylated pteroic acid photosensitizer has been synthesized and characterized. The compound name is decyl 4-(((2-amino-4-decyloxypteridin-6-yl)methyl)amino)benzoate and the synthesis was carried out in a reaction of 1-iododecane with pteroic acid and potassium carbonate in N,N-dimethylaniline (DMA). The decyl chain addition arises in a sequential manner, in which the mono-decyl compound is an intermediate and reacts rapidly to the bis-decyl product. Characterization data include 1D and 2D NMR, HPLC, UV-vis, mass spectrometry, and also will include data collected with density functional theory to compare the relative stabilities of various substituted bis-decylated pteroic acid regioisomers with the notion generating a gemini-type sensitizer surfactant to increase its lipophilicity for potential use in membrane localized photodynamics.