Synthesis and Ligand Binding of Tropane Ring Analogues of Paroxetine

Dec 13, 2004 - Michael J. Kuhar, Philip Abraham, Jason P. Bur- gess, Anita H. Lewin, and F. ... F.; Baldwin, R. M.; Riche, F.; Law, H.; Innis, R. B.;...
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J. Med. Chem. 2005, 48, 336

Additions and Corrections 2004, Volume 47 Alice Douangamath, Glenn E. Dale, Allan D’Arcy, Michael Almstetter, Robert Eckl, Annabelle Frutos-Hoener, Bernd Henkel, Katrin Illgen, Sven Nerdinger, Henk Schulz, Aengus Mac Sweeney, Michael Thormann, Andreas Treml, Sabine Pierau, Sjoerd Wadman, and Christian Oefner*: Crystal Structures of Staphylococcus aureus Methionine Aminopeptidase Complexed with Keto Heterocycle and Aminoketone Inhibitors Reveal the Formation of a Tetrahedral Intermediate. Page 1325. The spelling of coauthor Aengus Mac Sweeney was incorrect. The correct spelling is shown above. JM040812W 10.1021/jm040812w Published on Web 12/13/2004

1998, Volume 41 Kathryn I. Keverline-Frantz, John W. Boja, Michael J. Kuhar, Philip Abraham, Jason P. Burgess, Anita H. Lewin, and F. Ivy Carroll*: Synthesis and Ligand Binding of Tropane Ring Analogues of Paroxetine. Pages 247-257. A recent report (Ogier, L.; Turpin, F.; Baldwin, R. M.; Riche, F.; Law, H.; Innis, R. B.;

Tamagnan, G. Rearrangement of a mesylate tropane intermediate in nucleophilic substitution reactions. Synthesis of aza-bicyclo[3.2.1]octane and aza-bicyclo[3.2.2]nonane ethers, imides, and amines. J. Org. Chem. 2002, 67, 3637-3642) suggested that structures attributed by us to 4a, 4d, 7a, and 7d are incorrect. Our own re-investigation led us to conclude that compounds 4a, 4d, 7a, and 7d have aza-bicyclo[3.2.2]nonane structures as depicted in the accompanying graphic. These revised structures have been confirmed by NMR and X-ray analysis. Details of the study that led to the revision of the structures will be published separately. Page 250. Table 1 lists transporter binding potencies for a series of tropane ring analogues of paroxetine. The IC50 values for 7a and 7d should be attributed to the revised compounds. The IC50 values for the N-demethylated derivatives 4a and 4d should also be attributed to the revised compounds. Page 251. Compounds 4a and 4d in Figure 1 should correspond to the revised structures. The paragraph beginning with “The fact that several ...” should be disregarded. Page 253. The experimental details attributed to the synthesis of 7a now correspond to the revised derivative. Page 254. The experimental details attributed to the synthesis of 7d and 4a now correspond to the revised compounds. Page 255. The experimental details attributed to the synthesis of 4d now correspond to the revised compound. JM040189F 10.1021/jm040189f Published on Web 12/10/2004