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16
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5144227254
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note
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To ensure chiral integrity, diamine 8 was acylated with 2-naphthoyl chloride. The corresponding amide was then subjected to chiral HPLC analysis (Chiralpak AD) and was determined to be 96% ee, indicating that no significant racemization had occurred at the carbon atom bearing the phenyl ring
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17
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5144233102
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note
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(a)All new compounds showed physical and spectroscopic properties consistent with their structures
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18
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5144228561
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note
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3 (400 MHz) δ 7.75 (1H, br s), 7.73 (1H, d, J = 7.8 Hz), 7.64 (1H, d, J = 7.6 Hz), 7.52 (1H, t, J = 7.8 Hz), 7.35-7.25 (5H, m), 6.04 (1H, br t, J = 7.6 Hz), 5.68 (1H, m), 5.43 (1H, m), 4.49 (1H, d, J = 11.7 Hz), 4.25 (1H, d, J = 17.4 Hz), 3.36 (1H, dd, J = 7.6, 17.40 Hz), 3.29-3.23 (4H, m), 3.03 (1H, t, J = 10.7 Hz), 2.84 (2H, m), 2.63 (2H, s), 2.50 (3H, m), 1.77-1.71 (8H, m); LCMS m/z 494.3 (M+1)
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19
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5144228060
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note
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1H NMRs of the intermediate dienes were rather complex, the presence of rotomers notwithstanding, indicating a mixture of diastereomers. In one case, the mixture of dienes was separated and the major diene diastereomer so obtained was subjected to the ring closing metathesis reaction, affording exclusively the syn-product (unpublished observation); hence, the metathesis reaction was racemization free
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21
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0001538420
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Acid 16 required for 15 was prepared from allyl 3,4- dichlorophenoxyacetate 17 via the enolate Claisen rearrangement using the method of Burke: S.D. Burke, W.F. Fobare, and G.J. Pacofsky J. Org. Chem. 48 1993 5221 5228
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23
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84862431103
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50 = 50 nM
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50 = 50 nM
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24
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0028196592
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The 3-hydroxy analog 18 of 4a was prepared. The hydroxy group is known to enhance receptor affinity for κ: R. Gottschlich, K.A. Ackermann, A. Barber, G.D. Bartoszyk, and H.E. Greiner Bioorg. Med. Chem. Lett. 4 1994 677 682
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25
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5144225663
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note
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The RCM reaction proved to be a versatile reaction and was used to prepare higher order lactams, for example, 19.
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26
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2942607204
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S.J. Enna M. Williams J.W. Ferkany T. Kenakin R.D. Porsolt J.P. Sullivan John Wiley and Sons New York
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5144223447
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In vivo test methods: (a) Acetic acid-induced writhing: Mice were treated with vehicle or compound 4a and 15 min later injected with 0.6% acetic acid intraperitoneally. Five minutes after the administration of acetic acid, the number of writhes was counted for a 10 min period
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0344609779
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Formalin-induced flinching: Late phase formalin-induced flinching was determined using the method of D.L. DeHaven-Hudkins, L. Cortes Burgos, J.A. Cassel, J.D. Daubert, R.N. DeHaven, E. Mansson, H. Nagasaka, G. Yu, and T. Yaksh J. Pharmacol. Exp. Ther. 289 1999 494 502
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