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Volumn 16, Issue 21, 2006, Pages 5610-5615

Corrigendum to "Synthesis and α4β2 nicotinic affinity of unichiral 5-(2-pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes" [Bioorg. Med. Chem. Lett. 16 (2006) 5610-5615] (DOI:10.1016/j.bmcl.2006.08.020);Synthesis and α4β2 nicotinic affinity of unichiral 5-(2-pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes

Author keywords

Affinity; Benzodioxane; Ligand; nAChR; Nicotine; Oxazolidinone

Indexed keywords

1,4 BENZODIOXAN; 2 (10 METHYLPYRROLIDIN 20 YL) 1,4 BENZODIOXANE; 5 (10 METHYLPYRROLIDIN 20 YL) 1,3 OXAZOLIDIN 2 ONE; ALPHA 2 ADRENERGIC RECEPTOR; BENZODIOXAN DERIVATIVE; EFAROXAN; IDAZOXAN; IMILOXAN; NICOTINIC AGENT; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG; DIOXANE DERIVATIVE; NICOTINIC RECEPTOR; NICOTINIC RECEPTOR ALPHA4BETA2; OXAZOLIDINONE DERIVATIVE;

EID: 33748927613     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.10.039     Document Type: Erratum
Times cited : (20)

References (29)
  • 10
    • 33748942952 scopus 로고    scopus 로고
    • Walker, D. P.; Jacobsen, J. E.; Acker, B. A.; Groppi, V. E.; Piotrowski, D. W. PCT WO 03/042210, 2003.
  • 13
    • 33748928604 scopus 로고    scopus 로고
    • note
    • 3, 300 MHz) δ 1.50-1.90 (m, 4H), 2.35-2.60 (m, 2H), 3.20-4.20 (m, 8H), 5.00-5.20 (m, 2H), 7.15-7.45 (m, 15H). Analytical HPLC: LiChrospher 5 μm or μPorasil 10 μm column, 98:2 dichloromethane/methanol, 2 ml/min.
  • 14
    • 33748944298 scopus 로고    scopus 로고
    • note
    • 3, 300 MHz) δ 1.15-1.30 (m, 1H), 1.55-1.75 (m, 3H), 2.38 (s, 3H), 2.25-2.41 (m, 1H), 2.46-2.61 (m, 3H), 3.17-3.23 (m, 1H), 3.51 (d, J = 13.4 Hz, 2H), 3.72 (d, J = 13.4 Hz, 2H), 3.98 (t, 1H), 7.18-7.39 (m, 10H).
  • 15
    • 33748935716 scopus 로고    scopus 로고
    • note
    • 2O), 3.82-3.91 (m, 1H).
  • 16
    • 33748949058 scopus 로고    scopus 로고
    • note
    • 2: C, 56.45; H, 8.29; N, 16.46. Found: C, 56.22; H, 8.36; N, 16.35.
  • 17
    • 33748924113 scopus 로고    scopus 로고
    • note
    • Crystallographic data of 1 were obtained using an Enraf Nonius CAD-4 diffractometer (MoKα radiation) at room temperature. The structures were solved by direct methods [Altomare, A.; C. Burla, M.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Gagliardi, A.; Polidori, G. J. Appl. Crystallogr. 1994, 27, 435.] and the refinements were carried out by full-matrix least-squares using SHELX-97 [Sheldrick, G. M.; SHELX-97, University of Göttingen, Germany]. The absolute configuration of oxazolidinone asymmetric carbon was assigned on the basis of the known chirality of the pyrrolidine asymmetric centre. CCDC-616375 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: +44 1223 336 033; or deposit@ccdc.cam.ac.uk).
  • 18
    • 33748927784 scopus 로고    scopus 로고
    • Johnson, C. K.; ORTEP 11, Report ORNL-5138, Oak Ridge National Laboratory, TN, 1976.
  • 19
    • 33748942631 scopus 로고    scopus 로고
    • note
    • 1H NMR identical to the enantiomer.
  • 20
    • 33748943296 scopus 로고    scopus 로고
    • note
    • +); Analytical HPLC: μPorasil 10 μm column, 70:30 n-hexane/ethyl acetate, 1 ml/min.
  • 21
    • 33748930396 scopus 로고    scopus 로고
    • note
    • 4: C, 70.78; H, 6.24; N, 4.13. Found: C, 70.61; H, 6.31; N, 4.06.
  • 22
    • 33748927954 scopus 로고    scopus 로고
    • note
    • 3, 300 MHz): δ 1.24 (d, J = 6.2 Hz, 6H), 1.83-1.96 (m, 1H), 2.02-2.20 (m, 3H), 3.33-3.65 (m, 2H), 3.92 (dd, J = 9.2, 12.2 Hz, 1H), 4.20-4.44 (m, 3H), 4.90 (br s, 1H), 6.76-6.90 (m, 4H). Analytical HPLC: μPorasil 10 μm column, 70:30 n-hexane/ethyl acetate, 1 ml/min.
  • 23
    • 33748920330 scopus 로고    scopus 로고
    • note
    • 2: C, 61.06; H, 7.09; Cl, 13.86; N, 5.48. Found: C, 60.84; H, 7.01; Cl, 13.69; N, 5.43.
  • 24
    • 33748941402 scopus 로고    scopus 로고
    • note
    • 1H NMR identical to the enantiomer.
  • 28
    • 33748926412 scopus 로고    scopus 로고
    • note
    • The stereoisomers of 1 and 2 were built in their protonated form using the VEGA program (freely downloadable at www.ddl.unimi.it). Their conformational analyses were performed systematically rotating the interannular rotatable bond (yielding 360 conformers) and minimizing the obtained conformers to avoid high-energy geometries (conjugate gradients until rms = 0.01). The calculations were carried out using Quanta/CHARMm package (MSI, Burlington, MA) with the force-field CHARMm v22 and the atomic charges calculated by Gasteiger's method.


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