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47149097253
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Wu, D.1
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Ching, B.3
Hudson, S.4
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Gogas, K.7
Wade, W.S.8
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48649108672
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10.1016/j.bmcl.2008.07.050
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Hudson S., Kiankarimi M., Eccles W., Mostofi Y.S., Genicot M.J., Dwight W., Fleck B.A., Gogas K., and Wade W.S. Bioorg. Med. Chem. Lett. 18 (2008) 10.1016/j.bmcl.2008.07.050
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Hudson, S.1
Kiankarimi, M.2
Eccles, W.3
Mostofi, Y.S.4
Genicot, M.J.5
Dwight, W.6
Fleck, B.A.7
Gogas, K.8
Wade, W.S.9
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7
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0043022153
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Witherington J., Bordas V., Gaiba A., Naylor A., Rawlings A.D., Slingsby B.P., Smith D.G., Takle A.K., and Ward R.W. Bioorg. Med. Chem. Lett. 13 (2003) 3059
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Witherington, J.1
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Slingsby, B.P.6
Smith, D.G.7
Takle, A.K.8
Ward, R.W.9
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8
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Meyer, E.A.1
Furler, M.2
Diederich, F.3
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Klebe, G.5
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9
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48649091564
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note
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3, Z = 4, T = 208 K. R(F) = 6.30% based on 4918 independent reflections.
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10
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48649093105
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Kiankarimi, M.; Hudson, S.; Dwight, W. J.; Wade, W.S. Preparation of benzofuranylmethylamines, chromanylmethylamines, and thiochromanylmethylamines as monoamine reuptake inhibitors, US 2006252818.
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Kiankarimi, M.; Hudson, S.; Dwight, W. J.; Wade, W.S. Preparation of benzofuranylmethylamines, chromanylmethylamines, and thiochromanylmethylamines as monoamine reuptake inhibitors, US 2006252818.
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11
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48649084923
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note
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Recombinant CYP2D6 or CYP3A4 was incubated with a marker substrate and a NADPH-generating system for 30 min at 37 °C in the presence of varying concentrations of test compound. CYP3A4 activity was quantitated from the cleavage of substrate BFC to its fluorescent product 7-HFC. Ketoconazole was used as a positive control. CYP2D6 activity was quantitated from the cleavage of AMMC to its fluorescent product AHMC. Quinidine was used as positive control.
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12
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48649089800
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note
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Test compounds were incubated at 1 μM concentration in the presence of pooled human liver microsomes (0.5 mg/mL; n > 10; mixed gender) in the presence of an NADPH-generating system. The rate of disappearance of the parent compound was quantitated by LC/MS/MS at five time points over 60 min and the measured rate scaled to human body mass.
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15
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48649087997
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note
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Molecule structures were imported into the Molecular Operating Environment (MOE) software version 2007.09 and subjected to Stochastic Conformation Search using the MMFF94x force field with GBSA implicit solvation. Low energy conformations within 1.5 kcal/mol from the minimum that were most consistent with the known solid-state X-ray crystal structures were taken forward and aligned using the Flexible Alignment module using default field similarity terms except hydrogen-bonding terms were scaled down to 0.5. The best scoring alignment most consistent with known structure-activity patterns for NET:SERT selectivity was retained.
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17
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33846434461
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Preskorn S.H., Shah R., Neff M., Golbeck A.L., and Choi J. J. Psychiatr. Pract. 13 (2007) 5
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, pp. 5
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Preskorn, S.H.1
Shah, R.2
Neff, M.3
Golbeck, A.L.4
Choi, J.5
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18
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0037374043
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Skinner M.H., Kuan H.-Y., Pan A., Sathirakul K., Knadler M.P., Gonzales C.R., Yeo K.P., Reddy S., Lim M., Ayan-Oshodi M., and Wise S.D. Clin. Pharmacol. Ther. 73 (2003) 170
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Clin. Pharmacol. Ther.
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Skinner, M.H.1
Kuan, H.-Y.2
Pan, A.3
Sathirakul, K.4
Knadler, M.P.5
Gonzales, C.R.6
Yeo, K.P.7
Reddy, S.8
Lim, M.9
Ayan-Oshodi, M.10
Wise, S.D.11
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19
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48649096581
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note
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Calculated log Ps were determined using ACD/Log P DB, version 9.02, Advanced Chemistry Development, Inc., Toronto, ON, Canada, www.acdlabs.com, 2005. Calculated and measured values for atomoxetine, 3-I and 4-I were the same within experimental error.
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