Figure 1
From: Solenopsin A and analogs exhibit ceramide-like biological activity
Compounds studied in this paper and synthetic procedures for preparation of compounds S11-S15. (−)-Solenopsin A is a component of the venom of the fire ant solenopsis invicta. (+)-Solenopsin A is the enantiomer of the naturally occurring solenopsin. The structure of solenopsin resembles the structure of ceramides, which are fatty acid amides of sphingosine that play a crucial role in homeostasis of the skin and other organs. Solenopsin analogs S11-S14 were synthesized by deprotonation of 2,6-dimethylpyridine (S12-S14) or 2,4,6-trimethylpyridine (S11) by n-butyllithiium, followed by addition of alkyl bromides. Analog S15 was synthesized by treating pyridine-2-carboxaldehyde with the Grignard reagent decylmagnesium bromide. The solenopsin analogs (S11-S15) were successfully obtained after hydrogenation of the various 2-alkylpyridines.