Iodophenyl tagged sphingosine derivatives: Synthesis and preliminary biological evaluation

A facile synthesis of six 4-iodophenyl tagged sphingosine (SP) derivatives bearing alkyl chain lengths from 6 to 13 is described. The key steps for the assembly of these molecules, 5a–f, are Suzuki–Miyaura cross-coupling and cross-metathesis reactions. The feasibility of radiolabeling was demonstrated by synthesizing two 125I labeled compounds, [125I]5c and [125I]5e. In vitro enzyme assays indicated that the molecules, 5c–e, are potent inhibitors. Thus, they deserve further evaluation as potential radioactive probes for tumor imaging.

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