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D.P. Becker, G. DeCrescenzo, J. Freskos, D.P. Getman, S.L. Hockerman, M. Li, P. Mehta, G.E. Munie, and C. Swearingen Bioorg. Med. Chem. Lett. 11 2001 2723 2725
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33645353912
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U.S. Patent 6 583 299, 2003.
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Hockerman, S. L.; Becker, D. P.; Bedell, L. J.; DeCrescenzo, G.; Freskos, J. N.; Getman, D. P.; Heintz, R. M.; Li, M. H.; Mischke, B. V.; Villamil, C. I.; Barta, T. E. U.S. Patent 6 583 299, 2003.
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Hockerman, S.L.1
Becker, D.P.2
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33645329900
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Chem. Abstr. 134 2000 29702
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8
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11244267140
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For a review see: M. Zanda New J. Chem. 28 2004 1401 1411
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Zanda, M.1
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A. Aranyos, D.W. Old, A. Kiyomori, J.P. Wolfe, J.P. Sadighi, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 4369 4378
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14
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0028051675
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P. Bravo, S. Capelli, S.V. Meille, F. Viani, M. Zanda, V.P. Kukhar, and V.A. Soloshonok Tetrahedron: Asymmetry 5 1994 2009 2018
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Bravo, P.1
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Soloshonok, V.A.7
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15
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33645375696
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note
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Several unidentified by-products formed, according to TLC monitoring.
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-
-
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16
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33645352825
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-
note
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+] (4), 233 (23), 108 (82), 91 (100).
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-
-
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17
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33645367842
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-
note
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+] (22), 233 (100).
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19
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0037007703
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E. Buck, Z.J. Song, D. Tschaen, P.G. Dormer, R.P. Volante, and P.J. Reider Org. Lett. 4 2002 1623 1626
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Reider, P.J.6
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21
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0032474779
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M. Cowart, E.A. Kowaluk, J.F. Daanen, K.L. Kohlhaas, K.M. Alexander, F.L. Wagenaar, and J.F. Kerwin Jr. J. Med. Chem. 41 1998 2636 2642
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Kerwin Jr., J.F.7
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22
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33645346516
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note
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The striking difference of reactivity in the saponification reaction between sulfone 9 and sulfides 16 could be due to the difference of acidity of the α-sulfonyl and the α-sulfanyl protons.
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-
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23
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33645353911
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note
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These oxidations performed by m-CPBA at rt occurred in modest to fair yields, as a likely consequence of side reactions involving the hydroxamate moiety and/or the electron-rich aryl groups. In fact, several unidentified by-products were detected by TLC monitoring.
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24
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0026447262
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Full length MMP-1 was purchased from Biomol, and the activity of 1a measured by collagen gel zymography as previously described (see Ref. 18). The catalytic domains of MMP-3 and MMP-9 enzymes were produced in E. coli, transfected with cDNAs corresponding to the respective human sequences. Proteins were purified by affinity chromatography and the inhibitory potencies of racemic 1 and single enantiomers were assayed with synthetic, general MMP fluorescent substrate (Mca-PLGLDpaAR, Tebu-bio) using a FL600 Avantec fluorimeter. For MMP-3 see: Q.Z. Ye, L.L. Johnson, D.J. Hupe, and V. Baragi Biochemistry 31 1992 11231 11235
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Johnson, L.L.2
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Baragi, V.4
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26
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0042869970
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The effect on full length MMP-9 activity was evaluated as previously described: Inhibition of metalloproteinase-9 activity and gene expression by polyphenolic compounds isolated from the bark of Tristaniopsis calobuxus (Myrtaceae): S. Bellosta, M. Dell'Agli, M. Canavesi, N. Mitro, M. Monetti, M. Crestani, L. Verotta, N. Fuzzati, F. Bernini, and E. Bosisio Cell Mol. Life Sci. 60 2003 1440 1448
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Dell'Agli, M.2
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Monetti, M.5
Crestani, M.6
Verotta, L.7
Fuzzati, N.8
Bernini, F.9
Bosisio, E.10
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27
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4444339511
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For an outstanding recent example of bioactive Tfm-substituted molecules, see: A. Rivkin, F. Yoshimura, A.E. Gabarda, Y.S. Cho, T.-C. Chou, H. Dong, and S.J. Danishefsky J. Am. Chem. Soc. 126 2004 10913 10922
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Dong, H.6
Danishefsky, S.J.7
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28
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0842326690
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M. Sani, D. Belotti, R. Giavazzi, W. Panzeri, A. Volonterio, and M. Zanda Tetrahedron Lett. 45 2004 1611 1615
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Sani, M.1
Belotti, D.2
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Zanda, M.6
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