Szczepanska, Katarzyna;Karcz, Tadeusz;Mogilski, Szczepan;Siwek, Agata;Kuder, Kamil J.;Latacz, Gniewomir;Kubacka, Monika;Hagenow, Stefanie;Lubelska, Annamaria;Olejarz, Agnieszka;Kotanska, Magdalena;Sadek, Bassem;Stark, Holger;Kiec-Kononowicz, Katarzyna published 《Synthesis and biological activity of novel tert-butyl and tert-pentylphenoxyalkyl piperazine derivatives as histamine H3R ligands》. The research results were published in《European Journal of Medicinal Chemistry》 in 2018.Computed Properties of C11H16O The article conveys some information:
A series of twenty four new tert-Bu and tert-pentyl phenoxyalkylamine derivatives I [R = tetrahydrofuran-2-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrazin-2-yl; R1 = Me, Et; Q = (CH2)n, n = 1,2] was synthesized. Compounds with three to four carbon atoms alkyl chain spacer were evaluated for their binding properties at human histamine H3 receptor (hH3R). The highest affinities were observed for compounds I [R = pyridin-4-yl, R1 = Me, Q = (CH2)n, n = 1; R = pyridin-4-yl, R1 = Me, n = 2; R = pyridin-4-yl, R1 = Et, Q = (CH2)n, n = 1; R = pyridin-4-yl, R1 = Et, Q = (CH2)n, n = 2] (Ki=16.0-120nM). As it was showed in docking studies, those specific heteroaromatic 4-N piperazine substituents might interact with one of the key receptor interacting amino acids. Moreover, the most promising compounds exhibited anticonvulsant activity in the maximal electroshock-induced seizure (MES) model in mice. Furthermore, the blood-brain barrier penetration, the functional H3R antagonist potency as well as the pro-cognitive properties in the passive avoidance test were demonstrated for compound I [R = pyridin-4-yl, R1 = Me, Q = (CH2)n, n = 2]. In order to estimate drug-likeness of compound I [R = pyridin-4-yl, R1 = Me, Q = (CH2)n, n = 2] in silico and exptl. evaluation of metabolic stability in human liver microsomes was performed. In addition, paying attention to the results obtained within this study, the 4-pyridyl-piperazino moiety was established as a new bioisosteric piperidine replacement in H3R ligands. The experimental procedure involved many compounds, such as 4-tert-Amylphenol (cas: 80-46-6) .
4-tert-acylphenol (cas:80-46-6) contains hydroxyl group. Owing to the presence of the polar OH alcohols are more water-soluble than simple hydrocarbons. Methanol, ethanol, and propanol are miscible in water. Butanol, with a four-carbon chain, is moderately soluble.Computed Properties of C11H16O
Reference:
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