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85031192231
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Submitted to
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Lam, P. Y. S.; Clark, C. G.; Li, R.; Pinto, D. J. P.; Orwat, M. J.; Galemmo, R. J.; Fevig, J. M.; Alexander, R. S.; Smallwood, A. M.; Rossi, K. A.; Wright, M. R.; Bai, S.; He, K.; Luettgen, J. M.; Wong, P. C.; Knabb, R. M.; Wexler, R. R. Submitted to J. Med. Chem.
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Bai, S.12
He, K.13
Luettgen, J.M.14
Wong, P.C.15
Knabb, R.M.16
Wexler, R.R.17
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17
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0030783421
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(a) Quan M.L., Pruitt J.R., Ellis C.D., Liauw A.Y., Galemmo R.A., Stouten P.F.W., Wityak J., Knabb R.M., Thoolen M.J., Wong P.C., Wexler R.R. Bioorg. Med. Chem. Lett. 7:1997;2813
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Wityak, J.7
Knabb, R.M.8
Thoolen, M.J.9
Wong, P.C.10
Wexler, R.R.11
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18
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0033615010
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(b) Quan M.J., Liauw A.Y., Ellis C.D., Pruitt J.R., Bostrom L.L., Carini D.J., Huang P.P., Harrison K., Knabb R.M., Thoolen M.J., Wong P.C., Wexler R.R. J. Med. Chem. 42:1999;2752
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Carini, D.J.6
Huang, P.P.7
Harrison, K.8
Knabb, R.M.9
Thoolen, M.J.10
Wong, P.C.11
Wexler, R.R.12
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19
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0033615024
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(c) Quan M.J., Ellis C.D., Liauw A.Y., Alexander R., Knabb R.M., Lam G.N., Wong P.C., Wexler R.R. J. Med. Chem. 42:1999;2760
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Lam, G.N.6
Wong, P.C.7
Wexler, R.R.8
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During the course of our investigation, two isoxazoline library syntheses were reported. Solid phase: Cheng J.-F., Mjalli A.M.M. Tetrahedron Lett. 39:1998;939.
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During the course of our investigation, two isoxazoline library syntheses were reported. Solid phase: Fluorous phase:
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Curran, D.P.2
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23
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85031192339
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Representative procedure: 4-Chloro-3-nitrobenzaldehyde (279 mg, 1.5 mmol) was placed in a 4 mL plastic vial with an internal filter and a drain plug. Ethanol (2.5 mL) was added followed by the addition of an aqueous hydroxylamine hydrochloride solution (0.50 mL, 1.8 mmol, 3.74 M) and an aqueous sodium acetate solution (0.79 mL, 1.2 mmol, 1.52 M). The vial was rotated for 12 h on a Barnstead/Thermolyne Labquake Rotator. The ethanol and water are removed under a stream of nitrogen leaving a solid that was washed once with water and dried under dynamic vacuum to give 4-chloro-3-nitro-benzaldehyde oxime.
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85031190921
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-1.
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26
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85031187039
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-1.
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27
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0033615010
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Quan M.J., Liauw A.Y., Ellis C.D., Pruitt J.R., Bostrom L.L., Carini D.J., Huang P.P., Harrison K., Knabb R.M., Thoolen M.J., Wong P.C., Wexler R.R. J. Med. Chem. 42:1999;2752.
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Quan, M.J.1
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Ellis, C.D.3
Pruitt, J.R.4
Bostrom, L.L.5
Carini, D.J.6
Huang, P.P.7
Harrison, K.8
Knabb, R.M.9
Thoolen, M.J.10
Wong, P.C.11
Wexler, R.R.12
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28
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85031180280
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18 (5.00 g, 16.4 mmol) was heated to reflux in trifluoroacetic acid (80 mL) for 7 h. The solvent was evaporated and the solid judged to be of sufficient purity for further use.
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29
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85031183604
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2O in refluxing ethyl acetate.
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0037325621
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(a) Quan M.L., Ellis C.D., He M.Y., Liauw A.Y., Woerner F.J., Alexander R.S., Knabb R.M., Lam P.Y.S., Luettgen J.M., Wong P.C., Wright M.R., Wexler R.R. Bioorg. Med. Chem. Lett. 13:2003;369
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Bioorg. Med. Chem. Lett.
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Quan, M.L.1
Ellis, C.D.2
He, M.Y.3
Liauw, A.Y.4
Woerner, F.J.5
Alexander, R.S.6
Knabb, R.M.7
Lam, P.Y.S.8
Luettgen, J.M.9
Wong, P.C.10
Wright, M.R.11
Wexler, R.R.12
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31
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0037463812
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(b) Quan M.L., Ellis C.D., He M.Y., Liauw A.Y., Lam P.Y.S., Rossi K.A., Knabb R.M., Luettgen J.M., Wright M.R., Wong P.C., Wexler R.R. Bioorg. Med. Chem. Lett. 13:2003;1023.
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Bioorg. Med. Chem. Lett
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Quan, M.L.1
Ellis, C.D.2
He, M.Y.3
Liauw, A.Y.4
Lam, P.Y.S.5
Rossi, K.A.6
Knabb, R.M.7
Luettgen, J.M.8
Wright, M.R.9
Wong, P.C.10
Wexler, R.R.11
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32
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85031190138
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The 3-amino-4-chlorophenyl P1 moiety was incorporated into an analogous series and the pharmacokinetic profile examined in dog. This compound was found to be highly bioavailable (71%).
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