172733-78-7Relevant articles and documents
Structure-guided design and synthesis of P1′ position 1-phenylcycloalkylamine-derived pentapeptidic BACE1 inhibitors
Tagad, Harichandra D.,Hamada, Yoshio,Nguyen, Jeffrey-Tri,Hidaka, Koushi,Hamada, Takashi,Sohma, Youhei,Kimura, Tooru,Kiso, Yoshiaki
experimental part, p. 5238 - 5246 (2011/10/08)
Previously, we reported potent pentapeptidic BACE1 inhibitors with the hydroxymethylcarbonyl isostere as a substrate transition-state mimic. To improve the in vitro potency, we further reported pentapeptidic inhibitors with carboxylic acid bioisosteres at the P4 and P1′ positions. In the current study, we screened new P1′ position 1-phenylcycloalkylamine analogs to find non-acidic inhibitors that possess double-digit nanomolar range IC50 values. An extensive structure-activity relationship study was performed with various amine derivatives at the P1′ position. The most potent inhibitor of this pentapeptide series, KMI-1830, possessing 1-phenylcyclopentylamine at the P 1′ position had an IC50 value of 11.6 nM against BACE1 in vitro enzymatic assay.
A strategy for isotope containment during radiosynthesis - Devolatilisation of bromobenzene by fluorous-tagging-Ir-catalysed borylation en route to the 4-phenylpiperidine pharmacophore
Spivey, Alan C.,Martin, Laetitia J.,Tseng, Chih-Chung,Ellames, George J.,Kohler, Andrew D.
supporting information; experimental part, p. 4093 - 4095 (2009/02/07)
Syntheses of two 4-phenylpiperidines from bromobenzene have been developed involving anchoring to a fluorous-tag, Ir-catalysed borylation, Pd- and Co-catalysed elaboration then traceless cleavage. Although performed using 'cold' (i.e. unlabelled) bromoben
A reliable and efficient synthesis of SR 142801
Giardina,Grugni, Mario,Rigolio, Roberto,Vassallo, Marco,Erhard, Karl,Farina, Carlo
, p. 2307 - 2310 (2007/10/03)
A convenient synthesis of the potent human NK-3 receptor antagonist SR 142801, (S)-(+)-N-{{3-[1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]prop-1 -yl}-4-phenylpiperidin-4-yl}-N-methylacetamide [(S)-(+)-(15)], is described. Improvements over the previously reported procedure are the preparation of the intermediate 5 via the novel imide 3 and subsequent reaction with the nucleophile 14, which reacts, regioselectively, at the endocyclic nitrogen.