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10
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39749193552
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R.J. Cherney, R. Mo, D.T. Meyer, D.J. Nelson, Y.C. Lo, G. Yang, P.A. Scherle, S. Mandlekar, Z.R. Wasserman, H. Jezak, K.A. Solomon, A.J. Tebben, P.H. Carter, and C.P. Decicco J. Med. Chem. 51 2008 721
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Cherney, R.J.1
Mo, R.2
Meyer, D.T.3
Nelson, D.J.4
Lo, Y.C.5
Yang, G.6
Scherle, P.A.7
Mandlekar, S.8
Wasserman, Z.R.9
Jezak, H.10
Solomon, K.A.11
Tebben, A.J.12
Carter, P.H.13
Decicco, C.P.14
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11
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58549103078
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R.J. Cherney, J.B. Brogan, R. Mo, Y.C. Lo, G. Yang, P.B. Miller, P.A. Scherle, B.F. Molino, P.H. Carter, and C.P. Decicco Bioorg. Med. Chem. Lett. 19 2009 597
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(2009)
Bioorg. Med. Chem. Lett.
, vol.19
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Cherney, R.J.1
Brogan, J.B.2
Mo, R.3
Lo, Y.C.4
Yang, G.5
Miller, P.B.6
Scherle, P.A.7
Molino, B.F.8
Carter, P.H.9
Decicco, C.P.10
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12
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66349121609
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R.J. Cherney, R. Mo, D.T. Meyer, M.E. Voss, Y.C. Lo, G. Yang, P.B. Miller, P.A. Scherle, A.J. Tebben, P.H. Carter, and C.P. Decicco Bioorg. Med. Chem. Lett. 19 2009 3418
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(2009)
Bioorg. Med. Chem. Lett.
, vol.19
, pp. 3418
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Cherney, R.J.1
Mo, R.2
Meyer, D.T.3
Voss, M.E.4
Lo, Y.C.5
Yang, G.6
Miller, P.B.7
Scherle, P.A.8
Tebben, A.J.9
Carter, P.H.10
Decicco, C.P.11
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13
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84856229102
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Carter, P. H., Cherney, R. J., Batt, D. G., Duncia, J. V., Gardner, D. S., Ko, S. S., Srivastava, A. S., Yang, M. G. PCT Int. Appl. WO/PCT 2005021500, 2005
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Carter, P. H., Cherney, R. J., Batt, D. G., Duncia, J. V., Gardner, D. S., Ko, S. S., Srivastava, A. S., Yang, M. G. PCT Int. Appl. WO/PCT 2005021500, 2005.
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-
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14
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84856229106
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The absolute stereochemical assignments of 4d and 4e were confirmed by an independent synthesis of 4e from a known enantiomerically pure intermediate. See Ref. 13
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The absolute stereochemical assignments of 4d and 4e were confirmed by an independent synthesis of 4e from a known enantiomerically pure intermediate. See Ref. 13
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-
-
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16
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84856234832
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The stereochemical assignments of 20 and 21 were confirmed by NMR analyses on closely related compounds. Note that compounds derived from 21 were inactive towards CCR2 binding
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The stereochemical assignments of 20 and 21 were confirmed by NMR analyses on closely related compounds. Note that compounds derived from 21 were inactive towards CCR2 binding.
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-
-
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17
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84856235071
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For preparation of the (1,2,4)-trisubstituted analogs, see Ref. 12,13
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For preparation of the (1,2,4)-trisubstituted analogs, see Ref. 12,13
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18
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84856234833
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Carter, P. H., Cherney, R. J. PCT Int. Appl. WO2002/050019, 2002
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Carter, P. H., Cherney, R. J. PCT Int. Appl. WO2002/050019, 2002.
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19
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84856235069
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For the preparation of compounds 6a-c, see Carter, P. H., Cherney, R. J., Batt, D. G., Brown, G. D., Duncia, J. V., Gardner, D. S., Yang, M. G. PCT Int. Appl. WO2005/020899, 2005
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For the preparation of compounds 6a-c, see Carter, P. H., Cherney, R. J., Batt, D. G., Brown, G. D., Duncia, J. V., Gardner, D. S., Yang, M. G. PCT Int. Appl. WO2005/020899, 2005.
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20
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84856234529
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Note
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Conformational searching of 2b, 4b, 5b, 2c, 4c, and 5c, was carried out using the conformational search module of Macromodel v9.7 (Schrodinger, Inc.) and the OPLSAA-2005 force field in vacuum. Conformations were retained if they differed by 0.5A RMSD and had an energy <5 kcal/mol higher than the global minimum. Pairwise overlays of the resulting conformations of 2b and 4b were generated using ROCS (Openeye, Inc.) ranked by comboscore. The overlays were inspected and the best overlap selected. The conformation of 2b from this overlap was then used as the template molecule for the overlay of 5b. An identical sequence was used to align 2c, 4c, and 5c.
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22
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84856235070
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Carter, P. H., Duncia, J. V., Mudryk, B. M., Randazzo, M. E., Xiao, Z., Yang, M. G., Zhao, R. PCT Int. Appl. WO 2008/014360, 2008
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Carter, P. H., Duncia, J. V., Mudryk, B. M., Randazzo, M. E., Xiao, Z., Yang, M. G., Zhao, R. PCT Int. Appl. WO 2008/014360, 2008.
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