64263-81-6Relevant articles and documents
O-benzyl-N-tert-butoxycarbonyl-N-methyl-L-tyrosine
Jankowska, Elzbieta,Gilski, Miroslaw,Jaskolski, Mariusz,Grzonka, Zbigniew,Lankiewicz, Leszek
, p. o353-o354 (2002)
The crystal structure of the title compound, alternatively called 3-[4-(benzyloxy)phenyl]-2-(N-tert-butoxycarbonyl-N-methylamino)propionic acid, C22H27NO5, has been studied in order to examine the role of N-methylation as
Development of Novel Monoamine Oxidase-B (MAO-B) Inhibitors with Reduced Blood-Brain Barrier Permeability for the Potential Management of Noncentral Nervous System (CNS) Diseases
Gealageas, Ronan,Devineau, Alice,So, Pauline P. L.,Kim, Catrina M. J.,Surendradoss, Jayakumar,Buchwalder, Christian,Heller, Markus,Goebeler, Verena,Dullaghan, Edith M.,Grierson, David S.,Putnins, Edward E.
, p. 7043 - 7064 (2018/07/30)
Studies indicate that MAO-B is induced in peripheral inflammatory diseases. To target peripheral tissues using MAO-B inhibitors that do not permeate the blood-brain barrier (BBB) the MAO-B-selective inhibitor deprenyl was remodeled by replacing the terminal acetylene with a CO2H function, and incorporating a para-OCH2Ar motif (compounds 10a-s). Further, in compound 32 the C-2 side chain corresponded to CH2CN. In vitro, 10c, 10j, 10k, and 32 were identified as potent reversible MAO-B inhibitors, and all four compounds were more stable than deprenyl in plasma, liver microsomal, and hepatocyte stability assays. In vivo, they demonstrated greater plasma bioavailability. Assessment of in vitro BBB permeability showed that compound 10k is a P-glycoprotein (P-gp) substrate and 10j displayed mild interaction. Importantly, compounds 10c, 10j, 10k, and 32 displayed significantly reduced BBB permeability after intravenous, subcutaneous, and oral administration. These polar MAO-B inhibitors are pertinent leads for evaluation of efficacy in noncentral nervous system (CNS) inflammatory disease models.
An expeditious synthesis of the ascomycete metabolite rigidiusculamide B
Wunder, Anja,Schobert, Rainer
, p. 9262 - 9266 (2016/10/13)
The ascomycete metabolite rigidiusculamide B was synthesised in six steps and 22% overall yield. The key steps were a Li2Te-triggered Dittmer-type Dieckmann cyclisation of an N-(α-haloacyl)tyrosine ester to give a 4-O-silyl tetramate, followed
