%0 Journal Article
%A Baker, William C.
%A Choi, Michael J.
%A Hill, Daniel C.
%A Thompson, Julie L.
%A Petillo, Peter A.
%D 1999
%T Synthesis of Lipophilic Paramagnetic Contrast Agents
%U https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Lipophilic_Paramagnetic_Contrast_Agents/3716325
%R 10.1021/jo981920r.s001
%2 https://acs.figshare.com/ndownloader/files/5807889
%K series
%K monoalkylation
%K excess
%K gadolinium complexes 9
%K contrast agents
%K PCA
%K methodology
%K macrocycles 7
%K transformation
%K synthesis
%K carboxymethylated analogues 8
%K Alkylated cationic intermediates 6
%K yield
%K compound
%K alkyl iodides
%K cyclen
%K tunable lipophilicity
%K glyoxal adduct
%K Lipophilic Paramagnetic Contrast Agents
%K Synthesi
%X The facile, high-yielding synthesis of a series of macrocycles 7a−k in 75−100% yield is reported.
The transformation of these compounds to their carboxymethylated analogues 8a−k in 75−90%
yield and subsequent gadolinium complexes 9a−k provides a series of homologous neutral
paramagnetic contrast agents (PCAs) with tunable lipophilicity. Alkylated cationic intermediates
6a−k are prepared in yields of 72−94% from glyoxal adduct of cyclen (5) and slight excesses of
alkyl iodides. The methodology is selective for monoalkylation and amenable to large-scale synthesis.
%I ACS Publications