Ed in vacuo to provide a black cake. The cake was dissolved in dichloromethane (4 mL), along with the flask was flushed with argon. A resolution of diethylamine (0.055 g, 0.750 mmol) in anhydrous DCM (2 mL) was added by a syringe. The resulting green solution was stirred overnight and after that concentrated in vacuo. Trityls 11 and 15 were isolated by column chromatography on silica gel (TFA in DCM, 1:1000 v/v and then DCM saturated with aqueous ammonia) to provide pure 11 (0.062 g, 47 ) and 15 (0.057, 42 ) as a black powder (bluish-green in DCM remedy). Data for 15: MS (ESI): calcd. forNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptEuropean J Org Chem. Author manuscript; accessible in PMC 2014 April 24.Rogozhnikova et al.PageC41H49NS12 [M + H]+ 939.051; found 939.040. MALDI-TOF: calcd. for C41H48NS12 [M]+ 938.043; found 938.00. IR (KBr): = 2959 (s), 2922 (s), 2912 (s), 1450 (s), 1381 (s), 1363 (s), 1251 (s), 1167 (s), 1148 (s), 853 (m), 704 (m) cm-1. UV/Vis (CH2Cl2): max (, L mol-1 cm-1) = 270 (61100), 322 (16200), 445 (9120) nm. ESR: broad 1:two:1 triplet H = two.29 G; linewidth, 609 mG for 1 mM option in DCM; g = 2.0055. Spectra of trityl 15 are presented inside the Supporting Details. Option Preparation for Trityl 15 A answer of 3 (0.132 g, 0.146 mmol) in anhydrous dichloromethane (3 mL) and CF3SO3H (0.044 g, 0.293 mmol) was stirred at room temp. for 2 h below argon. The resulting deep green answer was added by syringe gradually more than 30 min to a stirred resolution of diethylamine (0.320 g, four.38 mmol) in DCM (1 mL). The homogeneous resolution was stirred overnight at area temp., and after that water (6 mL) was added. The mixture was stirred and left inside the air for 30 min. The organic phase was separated, along with the water phase was extracted with CH2Cl2 (three 3 mL). The combined organic extracts were filtered by means of a quick cotton plug and concentrated in vacuo. Column chromatography on silica gel (DCM/hexane, 1:1 v/v after which DCM) afforded trityl 15 (0.111 g, 82 ) because the only product.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptSupplementary MaterialRefer to Web version on PubMed Central for supplementary material.AcknowledgmentsThe PDE9 Inhibitor Species authors thank Drs. Leonid A. Shundrin and Denis A. Komarov for recording the ESR spectra and Dr. V. V. Koval for the registration of your MALDI-TOF spectra. The authors want to thank Professor Michael K. Bowman (University of Alabama, USA), Dr. Alexander M. Genaev and G E. Sal’nikov for the beneficial discussion and ideas. This study was supported by The Russian Foundation for Fundamental Analysis (P2X1 Receptor Antagonist custom synthesis project 13-04-00680A), The Ministry of Education and Science from the Russian Federation (project 8466) and the National Institute of Biomedical Imaging and Bioengineering, National Institute of Well being (NIH), grant quantity 5P41EB002034. NMR, IR, high resolution ESI-MS, and ESR experiments were carried out within the Chemical Service Center in the Siberian Branch on the Russian Academy of Sciences (RAS).
NIH Public AccessAuthor ManuscriptNat Neurosci. Author manuscript; obtainable in PMC 2014 December 05.Published in final edited kind as: Nat Neurosci. 2014 July ; 17(7): 97180. doi:10.1038/nn.3728.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptActive, phosphorylated fingolimod inhibits histone deacetylases and facilitates fear extinction memoryNitai C Hait1,two,six, Laura E Wise3,6, Jeremy C Allegood1,two, Megan O’Brien3, Dorit Avni1,two, Thomas M Reeves4, Pamela E Knapp4, Junyan.