-
3
-
-
0036230488
-
-
Nicolotti O., Pellegrini-Calace M., Altomare C., Carotti A., Carrieri A., and Sanz F. Curr. Med. Chem. 9 (2002) 1
-
(2002)
Curr. Med. Chem.
, vol.9
, pp. 1
-
-
Nicolotti, O.1
Pellegrini-Calace, M.2
Altomare, C.3
Carotti, A.4
Carrieri, A.5
Sanz, F.6
-
5
-
-
7244234606
-
-
Pallavicini M., Moroni B., Bolchi C., Clementi F., Fumagalli L., Gotti C., Vailati S., Valoti E., and Villa L. Bioorg. Med. Chem. Lett. 14 (2004) 5827
-
(2004)
Bioorg. Med. Chem. Lett.
, vol.14
, pp. 5827
-
-
Pallavicini, M.1
Moroni, B.2
Bolchi, C.3
Clementi, F.4
Fumagalli, L.5
Gotti, C.6
Vailati, S.7
Valoti, E.8
Villa, L.9
-
6
-
-
0034597576
-
-
Mullen G., Napier J., Balestra M., DeCory T., Hale G., Macor J., Mack R., Loch III J., Wu E., Kover A., Verhoest P., Sampognaro A., Phillips E., Zhu Y., Murray R., Griffith R., Blosser J., Gurley D., Machulskis A., Zongrone J., Rosen A., and Gordon J. J. Med. Chem. 43 (2000) 4045
-
(2000)
J. Med. Chem.
, vol.43
, pp. 4045
-
-
Mullen, G.1
Napier, J.2
Balestra, M.3
DeCory, T.4
Hale, G.5
Macor, J.6
Mack, R.7
Loch III, J.8
Wu, E.9
Kover, A.10
Verhoest, P.11
Sampognaro, A.12
Phillips, E.13
Zhu, Y.14
Murray, R.15
Griffith, R.16
Blosser, J.17
Gurley, D.18
Machulskis, A.19
Zongrone, J.20
Rosen, A.21
Gordon, J.22
more..
-
7
-
-
17144370948
-
-
Tatsumi R., Fujio M., Satoh H., Katayama J., Takanashi S., Hashimoto K., and Tanaka H. J. Med. Chem. 48 (2005) 2678
-
(2005)
J. Med. Chem.
, vol.48
, pp. 2678
-
-
Tatsumi, R.1
Fujio, M.2
Satoh, H.3
Katayama, J.4
Takanashi, S.5
Hashimoto, K.6
Tanaka, H.7
-
8
-
-
0030575611
-
-
Elliott R.L., Kopecka H., Gunn D.E., Lin N.H., Garvey D.S., Ryther K.B., Holladay M.W., Anderson D.J., and Campbell J.E. Bioorg. Med. Chem. Lett. 6 (1996) 2283
-
(1996)
Bioorg. Med. Chem. Lett.
, vol.6
, pp. 2283
-
-
Elliott, R.L.1
Kopecka, H.2
Gunn, D.E.3
Lin, N.H.4
Garvey, D.S.5
Ryther, K.B.6
Holladay, M.W.7
Anderson, D.J.8
Campbell, J.E.9
-
9
-
-
0029071709
-
-
Elliott R.L., Ryther K.B., David J.A., Raszkiewicz J.L., Campbell J.E., Sullivan J.P., and Garvey D.S. Bioorg. Med. Chem. Lett. 5 (1995) 991
-
(1995)
Bioorg. Med. Chem. Lett.
, vol.5
, pp. 991
-
-
Elliott, R.L.1
Ryther, K.B.2
David, J.A.3
Raszkiewicz, J.L.4
Campbell, J.E.5
Sullivan, J.P.6
Garvey, D.S.7
-
10
-
-
33748942952
-
-
Walker, D. P.; Jacobsen, J. E.; Acker, B. A.; Groppi, V. E.; Piotrowski, D. W. PCT WO 03/042210, 2003.
-
-
-
-
11
-
-
10744224639
-
-
Dei S., Bellucci C., Buccioni M., Ferrarono M., Gualtieri F., Guandalini L., Manetti D., Matucci R., Romanelli M.N., Scapecchi S., and Deodori E. Bioorg. Med. Chem. 11 (2003) 3153
-
(2003)
Bioorg. Med. Chem.
, vol.11
, pp. 3153
-
-
Dei, S.1
Bellucci, C.2
Buccioni, M.3
Ferrarono, M.4
Gualtieri, F.5
Guandalini, L.6
Manetti, D.7
Matucci, R.8
Romanelli, M.N.9
Scapecchi, S.10
Deodori, E.11
-
12
-
-
0026708262
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-
Ashton W.T., Cantone C.L., Meurer L.C., Tolman R.L., Greenlee W.J., Patchett A.A., Lynch R.J., Schorn T.W., Strouse J.F., and Siegl P.K.S. J. Med. Chem. 35 (1992) 2103
-
(1992)
J. Med. Chem.
, vol.35
, pp. 2103
-
-
Ashton, W.T.1
Cantone, C.L.2
Meurer, L.C.3
Tolman, R.L.4
Greenlee, W.J.5
Patchett, A.A.6
Lynch, R.J.7
Schorn, T.W.8
Strouse, J.F.9
Siegl, P.K.S.10
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13
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33748928604
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note
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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.
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14
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33748944298
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note
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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).
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15
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33748935716
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note
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2O), 3.82-3.91 (m, 1H).
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16
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33748949058
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note
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2: C, 56.45; H, 8.29; N, 16.46. Found: C, 56.22; H, 8.36; N, 16.35.
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-
-
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17
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33748924113
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note
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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).
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18
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33748927784
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Johnson, C. K.; ORTEP 11, Report ORNL-5138, Oak Ridge National Laboratory, TN, 1976.
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19
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33748942631
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note
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1H NMR identical to the enantiomer.
-
-
-
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20
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33748943296
-
-
note
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+); Analytical HPLC: μPorasil 10 μm column, 70:30 n-hexane/ethyl acetate, 1 ml/min.
-
-
-
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21
-
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33748930396
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note
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4: C, 70.78; H, 6.24; N, 4.13. Found: C, 70.61; H, 6.31; N, 4.06.
-
-
-
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22
-
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33748927954
-
-
note
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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.
-
-
-
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23
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33748920330
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note
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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.
-
-
-
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24
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33748941402
-
-
note
-
1H NMR identical to the enantiomer.
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-
-
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25
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12444305010
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Carbonelle E., Sparatore F., Canu-Boido C., Salvano C., Baldani-Guerra B., Terstappen G., Zwart R., Vijverberg H., Clementi F., and Gotti C. Eur. J. Pharmacol. 471 (2003) 85
-
(2003)
Eur. J. Pharmacol.
, vol.471
, pp. 85
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Carbonelle, E.1
Sparatore, F.2
Canu-Boido, C.3
Salvano, C.4
Baldani-Guerra, B.5
Terstappen, G.6
Zwart, R.7
Vijverberg, H.8
Clementi, F.9
Gotti, C.10
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27
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0032484715
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Uhlen S., Dambrova M., Nasman J., Schioth H.B., Gu Y., Wikberg-Matsson A., and Wikberg J.E. Eur. J. Pharmacol. 343 (1998) 93
-
(1998)
Eur. J. Pharmacol.
, vol.343
, pp. 93
-
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Uhlen, S.1
Dambrova, M.2
Nasman, J.3
Schioth, H.B.4
Gu, Y.5
Wikberg-Matsson, A.6
Wikberg, J.E.7
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28
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33748926412
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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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