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T.A. Blizzard, F. DiNinno, J.D. Morgan II, H.Y. Chen, J.Y. Wu, S. Kim, W. Chan, E.T. Birzin, Y. Yang, L. Pai, Y. Li, Z. Zhang, E.C. Hayes, C.A. DaSilva, P.M.D. Fitzgerald, N. Sharma, W. Tang, S.P. Rohrer, J.M. Schaeffer, and M.L. Hammond Bioorg. Med. Chem. Lett. 15 2005 107
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33544472772
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Aldrich Chemical Company.
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Aldrich Chemical Company.
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23
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33544458679
-
-
note
-
1H NMR. Selected compounds were characterized further by elemental analysis.
-
-
-
-
24
-
-
33544463935
-
-
note
-
Analytical chiral HPLC analysis was performed on a Chiralpak AD 4.6 × 250 mm 10 μm column eluted with 3:1 heptane/isopropanol at 0.4 mL/min. Under these conditions, the major (R,S)-diastereomer of 19 has a retention time of 23.7 min, while the minor (S,S)-diastereomer elutes at 15.1 min.
-
-
-
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25
-
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33544460877
-
-
note
-
1H NMR of the Mosher ester clearly showed the presence of only one diastereomer. By contrast, the corresponding NMR spectrum of the Mosher ester of the 1:1 diastereomeric mixture generated using racemic acid as the starting material clearly showed both diastereomers. Similarly, when the reaction sequence was run with racemic acid and racemic amine as starting materials, the NMR spectrum of the Mosher ester of the product showed ≥3 diastereomers.
-
-
-
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26
-
-
33544455153
-
-
note
-
50 values that are reproducible to within a factor of 2-3. Dihydrobenzoxathiin 1 (n = 36) and estradiol (n > 100) were tested in multiple assays; data reported in Table 1 are an average of all determinations.
-
-
-
-
27
-
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33544456389
-
-
note
-
Data for 7 and 8 reflect a 20 h incubation prior to radioactive quantification; all other data obtained with 3 h incubation.
-
-
-
-
28
-
-
33544465247
-
-
note
-
9c that measures estrogen agonism and antagonism in rat uterine tissue. Compounds are dosed orally at the indicated doses, except for fulvestrant, which was dosed subcutaneously. Agonism is reported as percentage of estradiol control; antagonism reported as percentage antagonism of estradiol.
-
-
-
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29
-
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33544468964
-
-
note
-
Estradiol exhibited 100% agonism at 4 μg/kg.
-
-
-
-
31
-
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33544471061
-
-
note
-
50 for the test compound is determined.
-
-
-
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33
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20044395599
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Q. Tan, T.A. Blizzard, J.D. Morgan II, E.T. Birzin, W. Chan, Y. Yang, L. Pai, E.C. Hayes, C.A. DaSilva, S.W. Mitra, J. Yudkovitz, H.A. Wilkinson, N. Sharma, P.M.D. Fitzgerald, S. Li, L. Colwell, J.E. Fisher, S. Adamski, A.A. Reszka, D. Kimmel, F. DiNinno, S.P. Rohrer, L.P. Freedman, J.M. Schaeffer, and M.L. Hammond Bioorg. Med. Chem. Lett. 15 2005 1675
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Tan, Q.1
Blizzard, T.A.2
Morgan II, J.D.3
Birzin, E.T.4
Chan, W.5
Yang, Y.6
Pai, L.7
Hayes, E.C.8
Dasilva, C.A.9
Mitra, S.W.10
Yudkovitz, J.11
Wilkinson, H.A.12
Sharma, N.13
Fitzgerald, P.M.D.14
Li, S.15
Colwell, L.16
Fisher, J.E.17
Adamski, S.18
Reszka, A.A.19
Kimmel, D.20
Dininno, F.21
Rohrer, S.P.22
Freedman, L.P.23
Schaeffer, J.M.24
Hammond, M.L.25
more..
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33544458898
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manuscript in preparation.
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Hayes, E. C. et al., manuscript in preparation.
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Hayes, E.C.1
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36
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33544456541
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manuscript in preparation.
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Warrier, S. et al., manuscript in preparation.
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Warrier, S.1
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