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Abstract Mono ‐ andbis ‐decylated lumazines have been synthesized and characterized. Namely,mono ‐decyl chain [1‐decylpteridine‐2,4(1,3H )‐dione]6a andbis ‐decyl chain [1,3‐didecylpteridine‐2,4(1,3H )‐dione]7a conjugates were synthesized by nucleophilic substitution (SN 2) reactions of lumazine with 1‐iododecane inN ,N ‐dimethylformamide (DMF) solvent. Decyl chain coupling occurred at theN 1site and then theN 3site in a sequential manner, without DMF condensation. Molecular orbital (MO) calculations show ap ‐orbital atN 1but notN 3, which along with a nucleophilicity parameter (N ) analysis predict alkylation atN 1in lumazine. Only after the alkylation atN 1in6a , does ap ‐orbital onN 3emerge thereby reacting with a second equivalent of 1‐iododecane to reach the dialkylated product7a . Data from NMR (1H,13C, HSQC, HMBC), HPLC, TLC, UV‐vis, fluorescence and density functional theory (DFT) provide evidence for the existence ofmono ‐decyl chain6a andbis ‐decyl chain7a . These results differ to pterinO ‐alkylations (kinetic control), whereN ‐alkylation of lumazine is preferred and then to dialkylation (thermodynamic control), with an avoidance of DMF solvent condensation. These findings add to the list of alkylation strategies for increasing sensitizer lipophilicity for use in photodynamic therapy. -
Fonseca, José Luis ; Sosa, María José ; Petroselli, Gabriela ; Erra‐Balsells, Rosa ; Quindt, Matías I. ; Bonesi, Sergio M. ; Greer, Alexander ; Greer, Edyta M. ; Thomas, Andrés H. ; Vignoni, Mariana ( , Photochemistry and Photobiology)
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Greer, Edyta M. ; Siev, Victor ; Segal, Ayelet ; Greer, Alexander ; Doubleday, Charles ( , Journal of the American Chemical Society)