119432-89-2Relevant academic research and scientific papers
Practical asymmetric synthesis of bioactive aminotetralins from a racemic precursor using a regiodivergent resolution
Webster, Robert,Boyer, Alistair,Fleming, Matthew J.,Lautens, Mark
supporting information; experimental part, p. 5418 - 5421 (2011/02/26)
Catalyst-controlled asymmetric ring opening of a racemic oxabicyclic alkene leads to two readily separable regioisomeric products both in excellent ee. A cationic Rh catalyst, with added NH4BF4 to modulate reactivity, was required to obtain synthetically useful yields. The utility of each substituted aminotetralin product has been demonstrated by their conversion to different biologically relevant molecules in a highly efficient and practical manner.
Characterization of the 5-HT7 Receptor. Determination of the Pharmacophore for 5-HT7 Receptor Agonism and CoMFA-Based Modeling of the Agonist Binding Site
Vermeulen, Erik S.,Schmidt, Anne W.,Sprouse, Jeffrey S.,Wikstr?m, H?kan V.,Grol, Cor J.
, p. 5365 - 5374 (2007/10/03)
On the basis of a set of 20 diverse 5-HT7 receptor agonists, the pharmacophore for 5-HT7 receptor agonism was determined. Additionally two CoMFA models were developed, based on different alignments of the agonists. Both models show good correlations between experimental and predictive pKi values and show a high degree of similarity. The CoMFA fields were subsequently used to map the agonist binding site of the model of the 5-HT7 receptor. Important roles in ligand binding are attributed to Asp162 of TM3 (interaction with a protonated nitrogen), and Thr244 of TM5 (interaction with a substituent at an aromatic moiety). Amino acid residues of the aromatic cluster of TM6 are hypothesized to play an important role in ligand binding as π-π stacking moieties. Agonists missing a hydrogen-bond-accepting moiety, but possessing an aromatic substituent instead, seem to bind the receptor with high affinity as well by occupying a lipophilic pocket hosted by residues of TM5 and TM6.
