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2
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Church, D.R.6
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Boothman, D.A.8
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4
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7
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Pinto C.N., de Moura K.C.G., Emery F.S., Pinto M.C.F.R., Castro S.L., Dantas A.P., Poloquevich P.F., Pinto A.V. Arzneim-Forsch. 50:2000;1120-1128.
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Castro, S.L.5
Dantas, A.P.6
Poloquevich, P.F.7
Pinto, A.V.8
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11
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85031195979
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PhD Thesis, Chemistry Institute /USP, São Carlos, SP, Brazil
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Malta, V. R. S. PhD Thesis, Chemistry Institute /USP, São Carlos, SP, Brazil, 2000.
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Malta, V.R.S.1
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Abken, H.-J.1
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Brodersen, J.3
Bäumer, S.4
Beifuss, U.5
Deppenmeier, U.6
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14
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0037204017
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Vicker N., Burgess L., Chuckowree I.S., Dodd R., Folkes A.J., Hardick D.J., Hancox T.C., Miller W., Milton J., Sohal S., Wang S.M., Wren S.P., Charlton P.A., Dangerfield W., Liddle C., Mistry P., Stewart A.J., Denny W.A. J. Med. Chem. 45:2002;721-739.
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Vicker, N.1
Burgess, L.2
Chuckowree, I.S.3
Dodd, R.4
Folkes, A.J.5
Hardick, D.J.6
Hancox, T.C.7
Miller, W.8
Milton, J.9
Sohal, S.10
Wang, S.M.11
Wren, S.P.12
Charlton, P.A.13
Dangerfield, W.14
Liddle, C.15
Mistry, P.16
Stewart, A.J.17
Denny, W.A.18
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15
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85031204366
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Phenazine 1 (0.314 g, 1 mmol) in a solution of dichloromethane (7 mL) was treated at room temperature with m-chloroperbenzoic acid (MCPBA) (1.72 g, 10 mmol) added in small portions. The reaction was followed by TLC. After the usual work up, the reaction product residue was submitted to column chromatography over silica gel and eluted with mixtures of hexane/ethyl acetate of increasing polarity to furnish compounds 2-4. Compound 2 was eluted with a mixture of hexane/ethyl acetate (100:1) and was recrystallized from acetone: the total yield of 2 in pure form was 27%. The two more polar products of the oxidation reaction, 3 and 4, were isolated in yields of 13% and 35%, respectively.
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Phenazine 1 (0.314 g, 1 mmol) in a solution of dichloromethane (7 mL) was treated at room temperature with m-chloroperbenzoic acid (MCPBA) (1.72 g, 10 mmol) added in small portions. The reaction was followed by TLC. After the usual work up, the reaction product residue was submitted to column chromatography over silica gel and eluted with mixtures of hexane/ethyl acetate of increasing polarity to furnish compounds 2-4. Compound 2 was eluted with a mixture of hexane/ethyl acetate (100:1) and was recrystallized from acetone: the total yield of 2 in pure form was 27%. The two more polar products of the oxidation reaction, 3 and 4, were isolated in yields of 13% and 35%, respectively.
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17
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85031195592
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3); 1.98 (1H, ddd, J=14.8, 5.4 and 4); 2.28 (1H, ddd, J=14.8, 12.2 and 4), 2.75 (1H, ddd, J=14.6, 12.2 and 4); 3.81 (1H, ddd, J=14.6, 5.4 and 4); 7.57 (1H, td, J=7.8 and 1.6; ArH); 7.61 (1H, dd, J=7.8 and 1.6; ArH); 7.72 (1H, td, J=7.6 and 1.6; ArH); 7.83-7.87 (2H, m, 2ArH); 8.09 (1H, dd, J=7.8 and 1.6; ArH); 8.14-8.17 (2H, m, ArH).
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3: C, 72.82%; H, 5.24%; N, 8.09%.
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18
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85031208863
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1=0.053.
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1=0.053.
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19
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85031194953
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2); 201.9 (CO)
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4 C, 69.60%; H, 5.01%; N 7.73%.
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20
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85031193827
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1=0.057.
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1=0.057.
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21
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85031204665
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note
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25.
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22
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0012864559
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Delft, The Netherlands: Nonius BV
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Nonius. COLLECT. Version 5.0. 1999;Nonius BV, Delft, The Netherlands.
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(1999)
COLLECT. Version 5.0
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Nonius1
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23
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0031059866
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Methods in Enzymology
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C.W. Jr. Carter, Sweet R.M. New York: Academic Press
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Otwinowski Z., Minor W. Methods in Enzymology. Carter C.W. Jr., Sweet R.M. Macromolecular Crystallography, Part A. 276:1997;307-326 Academic Press, New York.
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(1997)
Macromolecular Crystallography, Part A
, vol.276
, pp. 307-326
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Otwinowski, Z.1
Minor, W.2
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27
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85031195300
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2), 70.3 (C), 81.1 (C), 125.9 (CH), 127.4 (CH), 129.2 (CH), 129.5 (CH), 130.5 (CH), 130.6 (C), 130.7 (CH), 131.6 (CH)
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3 C, 72.44%; H, 5.79%; N, 8.04%.
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28
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0003467672
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For general discussion see. New York: Wiley
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For general discussion see March J. Advanced Organic Chemistry. 1992;1177-1182 Wiley, New York.
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(1992)
Advanced Organic Chemistry
, pp. 1177-1182
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March, J.1
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