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Ciszewski, G.; Gopalsamy, A.; Lim, K.; Park, K.; Shi, M.; Bloom, J.; Chopra, R.; Agarwal, A.; Krishnamurthy, G.; Ellingboe, J. W.; Upeslacis, J.; Mansour, T.; Condon, S. M.; LaPorte, M. G.; Miller, L. E.; Burns, C. J.; Howe, A. Y. M.; Orlowski, M.; van Zeijl, M.; O'Connell, J. 'Structure-Activity Relationship of Substituted Pyranoindoles as HCV RNA Dependent RNA Polymerase Inhibitors'. 229th American Chemical Society National Conference, March 2005, San Diego, California.
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more..
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77950861198
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note
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The tryptophol intermediate was constructed by Fischer-Indole cyclization of the corresponding hydrazone, see Ref. 10.
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0033538079
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The β-ketoesters were either commercially available or made by literature procedures. See:
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The β-ketoesters were either commercially available or made by literature procedures. See:. Lokot I.P., Pashkovsky F.S., and Lakhvich F.A. Tetrahedron 55 (1999) 4783
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Tetrahedron
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Lokot, I.P.1
Pashkovsky, F.S.2
Lakhvich, F.A.3
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77950859076
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note
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1H NMR and mass spectral analyses.
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33
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77950857518
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note
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2). The resulting esters were hydrolyzed using aqueous NaOH in THF/EtOH to give the desired pyranoindoles.
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34
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77950865685
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note
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50's are an average of multiple experiments with the standard deviations generally within 10% of this value.
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35
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77950861012
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note
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50) was the drug concentration that decreased the enzyme activity by 50% relative to control samples incubated without compound.
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36
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77950858137
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note
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The chiral β-ketoester derived from (S)-(+)-2-methylbutyric acid was prepared to afford diastereomeric pyranoindoles which were separated using chiral chromatography.
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37
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77950861255
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note
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Chiral HPLC separation using CHIRALPACK AD, mobile phase Heptane/IPA.
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38
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54849404284
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LaPorte M.G., Jackson R.W., Draper T.L., Gaboury J.A., Galie K., Herbertz T., Hussey A.R., Rippin S.R., Benetatos C.A., Chunduru S.K., Christensen J.S., Coburn G.A., Rizzo C.J., Rhodes G., O'Connell J., Howe A.Y.M., Mansour T., Collett M.S., Pevear D.C., Young D.C., Gao T., Tyrrell D.L.J., Kneteman N.M., Burns C.J., and Condon S.M. ChemMedChem 3 (2008) 1508
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Benetatos, C.A.9
Chunduru, S.K.10
Christensen, J.S.11
Coburn, G.A.12
Rizzo, C.J.13
Rhodes, G.14
O'Connell, J.15
Howe, A.Y.M.16
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Young, D.C.20
Gao, T.21
Tyrrell, D.L.J.22
Kneteman, N.M.23
Burns, C.J.24
Condon, S.M.25
more..
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39
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77950865234
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note
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At this point, the reason for the increased activities of the pyrazole containing compounds is not well understood.
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40
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33751157335
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For the preparation of α-ketoesters 15, See:
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For the preparation of α-ketoesters 15, See:. Wasserman H.H., and Ho W.B. J. Org. Chem. 59 (1994) 4364
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Wasserman, H.H.1
Ho, W.B.2
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42
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77950861197
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note
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-6 cm/s.
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