Synthesis of a nitrogen analogue of sphingomyelin as a sphingomyelinase inhibitor.
[structure: see text] Sphingomyelin nitrogen analogue 1 was designed and synthesized as a sphingomyelinase inhibitor. The synthesis was established by continuous Hofmann rearrangement and Crutius rearrangement as key steps in constructing the 3-hydroxy-1,2-diamine structure in the backbone of 1. This analogue showed moderate inhibitory activity toward SMase isolated from B. cereus.
Hakogi
Toshikazu
T
School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen Sanda, Hyogo 669-1337, Japan.
Taichi
Misako
M
Katsumura
Shigeo
S
D001409:Bacillus cereus / Q000201:enzymology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D013108:Sphingomyelin Phosphodiesterase / Q000037:antagonists & inhibitors*; D013109:Sphingomyelins / Q000138:chemical synthesis* / Q000737:chemistry
D004791:Enzyme Inhibitors; D013109:Sphingomyelins; D013108:Sphingomyelin Phosphodiesterase