Category: alcohols-buliding-blocks《Synthesis and biological activity of novel tert-amylphenoxyalkyl (homo)piperidine derivatives as histamine H3R ligands》 was published in 2017. The authors were Kuder, Kamil J.;Lazewska, Dorota;Kaleta, Maria;Latacz, Gniewomir;Kottke, Tim;Olejarz, Agnieszka;Karcz, Tadeusz;Fruzinski, Andrzej;Szczepanska, Katarzyna;Karolak-Wojciechowska, Janina;Stark, Holger;Kiec-Kononowicz, Katarzyna, and the article was included in《Bioorganic & Medicinal Chemistry》. The author mentioned the following in the article:
As a continuation of the authors’ search for novel histamine H3 receptor ligands a series of twenty new tert-amyl phenoxyalkylamine derivatives (2-21) was synthesized. Compounds of four to eight carbon atoms spacer alkyl chain were evaluated on their binding properties at human histamine H3 receptor (hH3R). The highest affinities were observed for the pentyl derivatives (Ki = 8.8-23.4 nM range) and among them piperidine derivative 1-(5-(4-(tert-pentyl)phenoxy)pentyl)piperidine hydrogen oxalate (6) with Ki = 8.8 nM. Structures (6), 3-methyl-1-(5-(4-(tert-pentyl)phenoxy)pentyl)piperidine hydrogen oxalate (7) were also classified as antagonists in cAMP accumulation assay (with EC50 = 157 and 164 nM, resp.). Moreover, new compounds were also evaluated for anticonvulsant activity in Antiepileptic Screening Program (ASP) at National Institute of Neurol. Disorders and Stroke (USA). Seven compounds showed anticonvulsant activity at maximal electroshock (MES) test in the dose of 30 mg/kg at 0.5 h. In the s.c. pentetrazole (scMET) test compound 4-methyl-1-(4-(4-(tert-pentyl)phenoxy)butyl)piperidine hydrogen oxalate (4) showed protection at 100 and 300 mg/kg dose at mice, however compounds showed high neurotoxicity in rotarod test at used doses. Also, mol. modeling studies were undertaken, to explain affinity of compounds at hH3R (taking into the consideration x-ray anal. of compound 1-(8-(4-(tert-pentyl)phenoxy)octyl)piperidine hydrogen oxalate (18)). To estimate “drug-likeness” of selected compounds in silico and exptl. evaluation of lipophilicity, metabolic stability and cytotoxicity was performed. To complete the study, the researchers used 4-tert-Amylphenol (cas: 80-46-6) .
4-tert-acylphenol (cas:80-46-6) contains hydroxyl group. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Category: alcohols-buliding-blocks
Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts