Potential sialyltransferase inhibitors based on neuraminyl substitution by hetaryl rings.
Replacement of the neuraminyl residue by a wide range of aryl rings in transition-state analogs of CMP-Neu5Ac led to readily accessible and potent inhibitors of alpha-(2-->6)- and alpha-(2-->3)-sialyltransferases. The synthesis of a series of potential sialyltransferase inhibitors in which the neuraminyl residue is replaced by hetaryl methylphosphonate residues (thiazole, benzothiazole, benzoxazole, benzothiophene and thiophene) is described in this paper.
Mathew
Bini
B
Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.
Schmidt
Richard R
RR
D003569:Cytidine Monophosphate N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D063065:Organophosphonates / Q000737:chemistry; D012799:Sialyltransferases / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D063065:Organophosphonates; D003569:Cytidine Monophosphate N-Acetylneuraminic Acid; D012799:Sialyltransferases