94420-55-0Relevant articles and documents
A new class of histamine H3 receptor antagonists derived from ligand based design
Roche, Olivier,Rodriguez Sarmiento, Rosa Maria
, p. 3670 - 3675 (2007)
Design and synthesis of highly potent and selective non-imidazole inverse agonists for the histamine H3 receptor is described. The study validates a new pharmacophore model based on the merging of two previously described models. It also demonstrates that the removal of the basic center potentially interacting with ASP3.32 and common to both models leads to loss of activity, whereas the replacement of the second basic center by an acceptor retains the potency.
Preparation of Regioselectively Protected Hydroquinones by Phosphorylation of p-Benzoquinones with Trialkyl Phosphites
Duthaler, Rudolf O.,Lyle, Paulette A.,Heuberger, Christoph
, p. 1406 - 1426 (2007/10/02)
The title reaction has been applied to 10 monosubstituted p-benzoquinones (Scheme 2, Table).The regioselectivity of the O-phosphorylation is influenced by bulky substituents (t-butyl and trimethylsilyl) and, electronically, by the methoxy group.The regioselectivity, which is high in nonpolar media (benzene), is lower in polar solvents (CH2Cl2 and CH3CN).The synthetic potential of this transformation, exemplified by the preparation of compounds 29 (Scheme 3) and 32 (Scheme 4), is considerably extended by applying milder methods for the phosphate hydrolysis and by using the reagent couple P(OCH3)3/trimethylsilyl chloride, which gives clean access to p-hydroxyphenyl phosphates. p-Benzoquinones 4h and 4i with strong ?-acceptor substituents react in a different way, giving phosphonates.The electronically induced regioselectivity of the O- and C-phosphorylation is in accordance with the preferences expected for the attack by a nucleophilic phosphorylation agent.