-
6
-
-
33746800698
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Chen C.W., Tran J.A., Jiang W., Tucci F.C., Arellano M., Wen J., Fleck B.A., Marinkovic D., White N.S., Pontillo J., Saunders J., Madan A., Foster A.C., and Chen C. Bioorg. Med. Chem. Lett. 16 (2006) 4800
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(2006)
Bioorg. Med. Chem. Lett.
, vol.16
, pp. 4800
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Chen, C.W.1
Tran, J.A.2
Jiang, W.3
Tucci, F.C.4
Arellano, M.5
Wen, J.6
Fleck, B.A.7
Marinkovic, D.8
White, N.S.9
Pontillo, J.10
Saunders, J.11
Madan, A.12
Foster, A.C.13
Chen, C.14
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7
-
-
4143067936
-
-
Mutulis F., Yahorava S., Mutule I., Yahorau A., Liepinsh E., Kopantshuk S., Veiksina S., Tars K., Belyakov S., Mishnev A., Rinken A., and Wikberg J.E.S. J. Med. Chem. 47 (2004) 4613
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(2004)
J. Med. Chem.
, vol.47
, pp. 4613
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Mutulis, F.1
Yahorava, S.2
Mutule, I.3
Yahorau, A.4
Liepinsh, E.5
Kopantshuk, S.6
Veiksina, S.7
Tars, K.8
Belyakov, S.9
Mishnev, A.10
Rinken, A.11
Wikberg, J.E.S.12
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8
-
-
38749102543
-
-
Ujjainwalla, F. 230thACS National Meeting, Washington, DC, USA. 2005, MEDI 275.
-
Ujjainwalla, F. 230thACS National Meeting, Washington, DC, USA. 2005, MEDI 275.
-
-
-
-
10
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38749089604
-
-
note
-
The sulfoxide 17 consisted of about 1:1 S- and R-isomers based on TLC analysis. They were not separated.
-
-
-
-
11
-
-
38749150421
-
-
For experimental detail, see: Chen, C.; Tran, J. A.; Tucci, F. C.; Chen, C. W.; Jiang, W.; Marinkovic, D.; Arellano, M.; White, N. S. WO 2005/040109.
-
For experimental detail, see: Chen, C.; Tran, J. A.; Tucci, F. C.; Chen, C. W.; Jiang, W.; Marinkovic, D.; Arellano, M.; White, N. S. WO 2005/040109.
-
-
-
-
12
-
-
38749110563
-
-
note
-
4, filtered, and concentrated in vacuo to afford trans-4-(4-chlorophenyl)-3-tetrahydrothiophenecarboxylic acid (trans-6) (625 mg, 96% yield).
-
-
-
-
18
-
-
22744457026
-
-
Kuo G.-H., Prouty C., Wang A., Emanuel S., DeAngelis A., Zhang Y., Song F., Beall L., Connolly P.J., Karnachi P., Chen X., Gruninger R.H., Sechler J., Fuentes-Pesquera A., Middleton S.A., Jolliffe L., and Murray W.V. J. Med. Chem. 48 (2005) 4892
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(2005)
J. Med. Chem.
, vol.48
, pp. 4892
-
-
Kuo, G.-H.1
Prouty, C.2
Wang, A.3
Emanuel, S.4
DeAngelis, A.5
Zhang, Y.6
Song, F.7
Beall, L.8
Connolly, P.J.9
Karnachi, P.10
Chen, X.11
Gruninger, R.H.12
Sechler, J.13
Fuentes-Pesquera, A.14
Middleton, S.A.15
Jolliffe, L.16
Murray, W.V.17
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24
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-
27444436362
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-
Jiang W., Chen C., Marinkovic D., Tran J.A., Chen C.W., Arellano L.M., White N.S., and Tucci F.C. J. Org. Chem. 70 (2005) 8924
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(2005)
J. Org. Chem.
, vol.70
, pp. 8924
-
-
Jiang, W.1
Chen, C.2
Marinkovic, D.3
Tran, J.A.4
Chen, C.W.5
Arellano, L.M.6
White, N.S.7
Tucci, F.C.8
-
25
-
-
38749146672
-
-
note
-
4, filtered, and concentrated in vacuo. The product 1-[2-[(1S)-1-(S-tert-butylsulfinylamino)-3-methylbutyl]-4-(trifluoromethyl)phenyl]-4-{[trans-4-(4-chlorophenyl)-tetrahydro-3-thiophenyl]carbonyl}piperazine was obtained by flash column chromatography (hexane/EtOAc 9:1-1:1) as a white foam (319 mg, 43 % yield).The above compound in MeOH (5 mL) was treated with HCl (4.0 M in 1,4-dioxane, 0.2 mL) for 0.5 h and the solution was concentrated in vacuo. One-fifth of the product was purified by HPLC to afford the titled compound trans-35 (27.8 mg, 43% yield).
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-
-
-
26
-
-
0037371579
-
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Nickolls S.A., Cismowski M.I., Wang X., Wolff M., Conlon P.J., and Maki R.A. J. Pharmacol. Exp. Ther. 304 (2003) 1217
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(2003)
J. Pharmacol. Exp. Ther.
, vol.304
, pp. 1217
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-
Nickolls, S.A.1
Cismowski, M.I.2
Wang, X.3
Wolff, M.4
Conlon, P.J.5
Maki, R.A.6
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27
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-
35848958619
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Chen C., Jiang W., Tucci F.C., Tran J.A., Fleck B.A., Hoare S.R., Joppa M., Markison S., Wen J., Sai Y., Johns M., Madan A., Chen C.W., Marinkovic D., Arellano M., Saunders J., and Foster A.C. J. Med. Chem. 50 (2007) 5249
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(2007)
J. Med. Chem.
, vol.50
, pp. 5249
-
-
Chen, C.1
Jiang, W.2
Tucci, F.C.3
Tran, J.A.4
Fleck, B.A.5
Hoare, S.R.6
Joppa, M.7
Markison, S.8
Wen, J.9
Sai, Y.10
Johns, M.11
Madan, A.12
Chen, C.W.13
Marinkovic, D.14
Arellano, M.15
Saunders, J.16
Foster, A.C.17
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28
-
-
33746206349
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Jiang W., Tucci F.C., Chen C.W., Arellano M., Tran J.A., White N.S., Marinkovic D., Pontillo J., Fleck B.A., Wen J., Saunders J., Madan A., Foster A.C., and Chen C. Bioorg. Med. Chem. Lett. 16 (2006) 4674
-
(2006)
Bioorg. Med. Chem. Lett.
, vol.16
, pp. 4674
-
-
Jiang, W.1
Tucci, F.C.2
Chen, C.W.3
Arellano, M.4
Tran, J.A.5
White, N.S.6
Marinkovic, D.7
Pontillo, J.8
Fleck, B.A.9
Wen, J.10
Saunders, J.11
Madan, A.12
Foster, A.C.13
Chen, C.14
-
29
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38749140068
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note
-
Based on our previous work, there is only a small (2-fold) affinity difference between the 6-fluorophenylpiperazine and the 4-(trifluoromethyl)phenylpiperazine analogs. See Ref. 6.
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-
-
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30
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34547881486
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Tran J.A., Chen C.W., Jiang W., Tucci F.C., Fleck B.A., Marinkovic D., Arellano M., and Chen C. Bioorg. Med. Chem. Lett. 17 (2007) 5165
-
(2007)
Bioorg. Med. Chem. Lett.
, vol.17
, pp. 5165
-
-
Tran, J.A.1
Chen, C.W.2
Jiang, W.3
Tucci, F.C.4
Fleck, B.A.5
Marinkovic, D.6
Arellano, M.7
Chen, C.8
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