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16
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34447120352
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note
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2 (30 mg, 0.042 mmol) were added; the reaction mixture was degassed again and then stirred under inert atmosphere at 65 °C. The reaction was monitored by TLC....
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19
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34447136315
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note
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3P in cyclohexane (0.15 M, 0.40 mL, 0.060 mmol) were added. The reaction mixture was stirred at 50 °C for 90 min, cooled down, and 10% aqueous solution of potassium fluoride was added. The mixture was stirred for 10 min, filtered through a pad of silica gel and the silica gel was washed with ethyl acetate (50 mL). The filtrate was washed with brine (3 × 15 mL), 10% aqueous solution of potassium fluoride (2 × 10 mL), water (2 × 10 mL), and brine (3 × 15 mL). The organic solution was dried with sodium sulfate, concentrated and purified by flash column chromatography (silica gel, hexanes/ethyl acetate 10:1). The crude product was triturated with hexanes/ethyl acetate mixture (15:1, 16 mL) yielding methyl (Z)-[2-methyl-4-[3-[4-(5-methylthiophen-2-yl)phenyl]-5-phenylpent-2- en-4-ynyloxy]phenoxy] acetate (14n) as a yellowish amorphous mass in 47% yield.
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20
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0035846209
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Morimoto H., Shimadzu H., Kushiyama E., Kawanishi H., Hosaka T., Kawase Y., Yasuda K., Kikkawa K., Yamauchi-Kohno R., and Yamada K. J. Med. Chem. 44 (2001) 3355
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Kikkawa, K.8
Yamauchi-Kohno, R.9
Yamada, K.10
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21
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0031934860
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6-Iodo-3-methylbenzofuran was prepared as described in Ref.
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6-Iodo-3-methylbenzofuran was prepared as described in Ref. Hongu M., Tanaka T., Funami N., Saito K., Arakawa K., Matsumoto M., and Tsujihara K. Chem. Pharm. Bull. 46 (1998) 22
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22
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0034670508
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Tretyakov E., Tkachev A.V., Rybalova T.V., Gatilov Y.V., Knight D.V., and Vasilevsky S.F. Tetrahedron 56 (2000) 10075
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25
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34447123402
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PPAR in-vitro transactivation assay was performed as described in Ref. 11.
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26
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34447123401
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note
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27,28 6f was built in Maestro version 7.5, a formal charge of -1 was assigned, and the molecule was minimized with the OPLS_2005 force field. 6f was docked with Glide version 4.0 using the SP mode and the van der Waals radii of the ligand atoms were scaled by 0.8.
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27
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12144289984
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Friesner R.A., Banks J.L., Murphy R.B., Halgren T.A., Klicic J.J., Mainz D.T., Repasky M.P., Knoll E.H., Shaw D.E., Shelley M., Perry J.K., Francis P., and Shenkin P.S. J. Med. Chem. 47 (2004) 1739
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Mainz, D.T.6
Repasky, M.P.7
Knoll, E.H.8
Shaw, D.E.9
Shelley, M.10
Perry, J.K.11
Francis, P.12
Shenkin, P.S.13
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28
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1642310340
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Halgren T.A., Murphy R.B., Friesner R.A., Beard H.S., Frye L.L., Pollard W.T., and Banks J.L. J. Med. Chem. 47 (2004) 1750
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Pollard, W.T.6
Banks, J.L.7
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