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. 2018 Sep 4;9(10):1051–1056. doi: 10.1021/acsmedchemlett.8b00361

Scheme 2. Synthesis and Evaluation of Simplified 6HP-Phosphorylcholine Hybrids 12.

Scheme 2

(A) Reagents and conditions: (a) 2-chloro-1,3,2-dioxaphospholane 2-oxide, TEA, toluene, 23 °C; 4 h; (b) trimethylamine, MeCN, 90 °C, 16 h; (c) conc. aq. HCl, MeCN, 23 °C; 10 min. 12–49% over three steps and after purification by preparative HPLC. (B) Luciferase reporter assay demonstrating ligand efficacy, each bar represents activity at a different concentration of designated compound, from right to left: 0.003, 0.03, 0.3, 1.0, 3.0, 10, and 30 μM. Represented as a measure of fold increase in activity over vehicle. (C) Overlay of DLPC and RJW100 in LRH-1 LBD. Number of atoms in linker is counted between the 6HP core and key PC binding element.