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Preskorn, S. H.; Ross, R.; Stanga, C. Y. Selective serotonin reuptake inhibitors Handb. Exp. Pharmacol. 2004, 157, 241-262
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Spinks, D.; Spinks, G. Serotonin reuptake inhibition: an update on current research strategies Curr. Med. Chem. 2002, 9, 799-810
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Spinks, D.1
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Denhart, D. J.; Mattson, R. J.; Ditta, J. L.; Macor, J. E. One-pot synthesis of homotryptamines from indoles Tetrahedron Lett. 2004, 45, 3803-3805
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Homotryptamines as potent and selective serotonin reuptake inhibitors (SSRIs)
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Schmitz, W. D.; Denhart, D. J.; Brenner, A. B.; Ditta, J. L.; Mattson, R. J.; Mattson, G. K.; Molski, T. F.; Macor, J. E. Homotryptamines as potent and selective serotonin reuptake inhibitors (SSRIs) Bioorg. Med. Chem. Lett. 2005, 15, 1619-1621
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MacOr, J.E.8
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Conformationally Restricted Homotryptamines. Indole Cyclopropylmethylamines as Selective Serotonin Reuptake Inhibitors
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Mattson, R. J.; Catt, J. D.; Denhart, D. J.; Deskus, J. A.; Ditta, J. L.; Higgins, M. A.; Marcin, L. R.; Sloan, C. P.; Beno, B. R.; Gao, Q.; Cunningham, M. A.; Mattson, G. K.; Molski, T. F.; Taber, M. T.; Lodge, N. J. Conformationally Restricted Homotryptamines. Indole Cyclopropylmethylamines as Selective Serotonin Reuptake Inhibitors J. Med. Chem. 2005, 48, 6023-6034
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Higgins, M.A.6
Marcin, L.R.7
Sloan, C.P.8
Beno, B.R.9
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Cunningham, M.A.11
Mattson, G.K.12
Molski, T.F.13
Taber, M.T.14
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Enantioselective Synthesis of a Highly Potent Selective Serotonin Reuptake Inhibitor. An Application of Imidazolidinone Catalysis to the Alkylation of Indoles with an α,β-Disubstituted α,β- Unsaturated Aldehyde
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King, H. D.; Meng, Z.; Denhart, D.; Mattson, R.; Kimura, R.; Wu, D.; Gao, Q.; Macor, J. E. Enantioselective Synthesis of a Highly Potent Selective Serotonin Reuptake Inhibitor. An Application of Imidazolidinone Catalysis to the Alkylation of Indoles with an α,β-Disubstituted α,β- Unsaturated Aldehyde Org. Lett. 2005, 7, 3437-3440
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Conformationally restricted homotryptamines. Part 4: Heterocyclic and naphthyl analogs of a potent selective serotonin reuptake inhibitor
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King, H. D; Denhart, D. J.; Deskus, J. A.; Ditta, J. L.; Epperson, J. R.; Higgins, M. A.; Kung, J. E.; Marcin, L. R.; Sloan, C. P.; Mattson, G. K.; Molski, T. F.; Krause, R. G.; Bertekap, R. L.; Lodge, N. J.; Mattson, R. J.; Macor, J. E. Conformationally restricted homotryptamines. Part 4: Heterocyclic and naphthyl analogs of a potent selective serotonin reuptake inhibitor Bioorg. Med. Chem. Lett. 2007, 17, 5647-5651
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Higgins, M.A.6
Kung, J.E.7
Marcin, L.R.8
Sloan, C.P.9
Mattson, G.K.10
Molski, T.F.11
Krause, R.G.12
Bertekap, R.L.13
Lodge, N.J.14
Mattson, R.J.15
MacOr, J.E.16
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Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors
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Deskus, J. A.; Epperson, J. R.; Sloan, C. P.; Cipollina, J. A.; Dextraze, P.; Qian-Cutrone, J.; Gao, Q.; Ma, B.; Beno, B. R.; Mattson, G. K.; Molski, T. F.; Krause, R. G.; Taber, M. T.; Lodge, N. J.; Mattson, R. J. Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors Bioorg. Med. Chem. Lett. 2007, 17, 3099-3104
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Dextraze, P.5
Qian-Cutrone, J.6
Gao, Q.7
Ma, B.8
Beno, B.R.9
Mattson, G.K.10
Molski, T.F.11
Krause, R.G.12
Taber, M.T.13
Lodge, N.J.14
Mattson, R.J.15
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Conformationally restricted homotryptamines. Part 5: 3-(trans -2-aminomethylcyclopentyl)indoles as potent selective serotonin reuptake inhibitors
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Denhart, D. J.; Deskus, J. A.; Ditta, J. L.; Gao, Q.; King, H. D.; Kozlowski, E. S.; Meng, Z.; LaPaglia, M. A.; Mattson, G. K.; Molski, T. F.; Taber, M. T.; Lodge, N. J.; Mattson, R. J.; Macor, J. E. Conformationally restricted homotryptamines. Part 5: 3-(trans -2-aminomethylcyclopentyl)indoles as potent selective serotonin reuptake inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 4031-4033
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Kozlowski, E.S.6
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Lapaglia, M.A.8
Mattson, G.K.9
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Taber, M.T.11
Lodge, N.J.12
Mattson, R.J.13
MacOr, J.E.14
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Neurochemical, pharmacokinetic, and behavioral effects of the novel selective serotonin reuptake inhibitor BMS-505130
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Taber, M. T.; Wright, R. N.; Molski, T. F.; Clarke, W. J.; Brassil, P. J.; Denhart, D. J.; Mattson, R. J.; Lodge, N. J. Neurochemical, pharmacokinetic, and behavioral effects of the novel selective serotonin reuptake inhibitor BMS-505130 Pharmacol., Biochem. Behav. 2005, 80, 521-528
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Mattson, R.J.7
Lodge, N.J.8
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Kaluzna, I. A.; Rozzell, J. D.; Kambourakis, S. Ketoreductases: stereoselective catalysts for the facile synthesis of chiral alcohols Tetrahedron: Asymmetry 2005, 16, 3682-3689
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An analogous resolution of the CN-ketone 5a proved unsuccessful. We were unable to crystallize either of the diastereomers formed upon condensation of 5a with (1 S,2 S)-1,2-diphenylethane-1,2-diol
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An analogous resolution of the CN-ketone 5a proved unsuccessful. We were unable to crystallize either of the diastereomers formed upon condensation of 5a with (1 S,2 S)-1,2-diphenylethane-1,2-diol.
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15
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47949118793
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The conformers of compounds 3 and 8a shown in Figure 2 were identified as follows: Initially, 7500 step Monte Carlo conformational searches with 2500 steps of PRCG (16) energy minimization per conformer using the OPLS2005 force-field (17) and GB/SA implicit water solvation model (18) were performed for compounds 3 and 8a in their N-protonated cationic forms using MacroModel version 9.5; Schrödinger, LLC: New York, NY, 2007. For each compound, the set of conformations obtained was then ranked in ascending order of OPLS2005 GB/SA energy and clustered using a non-hydrogen atom RMSD cutoff of 0.25 Å. The lowest energy conformer from each cluster was then optimized using density functional theory (DFT) calculations with the B3LYP functional, 6-31+G* basis set and a self-consistent reaction field implicit water solvation model. (19, 20) DFT calculations were performed with Jaguar version 7.0; Schrödinger, LLC: New York, NY, 2007. For compounds 3 and 8a, the lowest-energy DFT-optimized conformer that yielded a reasonable three-point overlay (see text) with the conformer of sertraline shown in Figure 5a of reference 6 was selected.
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MacroModel Version 9.5
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16
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0001903222
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Note sur la convergence de méthodes de directions conjuguées
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Polak, E.1
Ribiere, G.2
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0029912748
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Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids
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Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids J. Am. Chem. Soc. 1996, 118, 11225-11236
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0344778061
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Semianalytical treatment of solvation for molecular mechanics and dynamics
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Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. A. Semianalytical treatment of solvation for molecular mechanics and dynamics J. Am. Chem. Soc. 1990, 112, 6127-6129
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68049117647
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For details of the B3LYP DFT functional and implicit solvation method used see:; Schrodinger, LLC: New York, NY, and references therein
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For details of the B3LYP DFT functional and implicit solvation method used see: Jaguar 7.0 User Manual; Schrodinger, LLC: New York, NY, 2007, and references therein.
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Jaguar 7.0 User Manual
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20
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Hehre, W.J.1
Radom, L.2
Schleyer V. P, R.3
Pople, J.A.4
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