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Supplementary information.
Structure Activity Relationship of trans-Substituted-Propenoic Acid Derivatives on the Nicotinic Acid Receptor HCA2 (GPR109A).
J.P.D. van Veldhoven, C.C. Blad, C.M. Artsen, C. Klopman, D.R. Wolfram, M.J. Abdelkadir, J.R. Lane, J. Brussee and A.P. IJzerman
Division of Medicinal Chemistry, Leiden/Amsterdam Center for Drug Research, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
1. Chemistry.
All reagents used were obtained from commercial sources and all solvents were of analytical grade. 1H and 13C NMR spectra were recorded on a Bruker AV 400 (1H NMR, 400 MHz; 13C NMR, 100 MHz) spectrometer with tetramethylsilane as an internal standard. Chemical shifts are reported in δ (ppm) and the following abbreviations are used: s = singlet, d = doublet, dd = double doublet, t = triplet, m = multiplet, br = broad, ar = aromatic protons, ph = phenyl protons. Elemental analyses were performed by the Leiden Institute of Chemistry and are within 0.4% of the theoretical values unless otherwise stated or purity was confirmed by HPLC and High Resolution Mass Spectroscopy. HPLC was performed on a Gilson 306 system (detection at 254 nm) equipped with an analytical C18 column (4.6 mm x 12.5 cm, 5 μm) in combination with a gradient of mixture A: 1 MeCN / 9 H2O, B: 9 MeCN / 1 H2O. High resolution mass spectra were recorded by direct injection on a mass spectrometer (Thermo Finnigan LTQ Orbitrap) equipped with an electro spray ion source in positive mode (source voltage 3.5 kV, sheath gas flow 10, capillary temperature 250 °C) with resolution R = 60000 at m/z 400 (mass range m/z = 150‐2000) and dioctyl phthalate (m/z = 391.2842) as a “lock mass”. Reactions were routinely monitored on TLC using Merck silica gel F254 plates. Microwave reactions were performed in an Emrys Optimizer (Biotage AB, formerly Personal Chemistry). Wattage was automatically adjusted so as to maintain the desired temperature. The yields of all products were not optimize
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