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0009612103
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Present address: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556.
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Present address: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556.
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2
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Kingston, D. G. I. Recent advances in the chemistry and structure-activity relationships of paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; George, G. I.; Chen, T. T.; Ojima, I.; and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp 203-216.
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Han, Y.; Ghaudhary, A. G.; Chordia, M. D.; Sackett, D. L.; Perez-Ramirez, B.; Kingston, D. G. I.; Bane, S. Biochemistry 1996, 35, 14173-14183.
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Chen, S.-H.; Wei, J.-M.; Long, B. H.; Fairchild, C. A.; Carboni, J.; Mamber, S. W.; Rose, W. C.; Johnston, K.; Casazza, A. M.; Kadow, J. F.; Farina, V.; Vyas, D.; Doyle, T. W. Bioorg. & Med. Chem. Lett. 1995, 5, 2741-2746.
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Vyas, D.12
Doyle, T.W.13
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Liang, X.; Kingston, D. G. I.; Lin, C. M.; Hamel, E. Tetrahedron Lett. 1995, 36, 2901-2904.
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Liang, X.1
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Hamel, E.4
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Liang, X.; Kingston, D. G. I.; Long, B. H.; Fairchild, C. A.; and Johnston, K. A. Tetrahedron Lett. 1997, 53, 3441-3456.
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0028235069
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Chaudhary, A. G.; Gharpure, M.; Rimoldi, J. M.; Chordia, M. D.; Gunatilaka, A. A. L.; Kingston, D. G. I.; Grover, S.; Lin, C. M.; Hamel, E. J. Am. Chem. Soc. 1994, 116, 4097.
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Kingston, D.G.I.6
Grover, S.7
Lin, C.M.8
Hamel, E.9
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0028071455
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For a similar example, see Datta, A.; Aube, J.; Georg, G. I.; Mitscher, L. A. Bioorg. Med. Chem. Lett. 1994, 4, 1831.
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Datta, A.1
Aube, J.2
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Mitscher, L.A.4
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0009568029
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note
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Various hypothetical bridged analogs were examined by changing the linker between C-4 and C-6 as well as the C-4 acyl moiety, the minimized energy was compared to determine the relative stability of the analogs. During the modeling studies, it was found that certain chains such as unsaturated di-acids or phenylene dialkyl di-acids at the C-4 position might be better than the glutaric acid in both terms of entropy (less degree of freedom) and product stability (less trans-annular interactions). Because of the unavailability of the appropriate reagents and the problems encountered in the C-4 acylation using the synthetic reagents, it was decided to simplify the question by choosing glutaric acid as the acyl source at C-4.
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Kingston, D. G. I.; Chaudhary, A. G.; Chordia, M. D.; Gharpure, M.; Gunatilaka, A. A. L.; Higgs, P. I.; Rimoldi, J. M.; Samala, L.; Jagtap, P. G.; Giannakakou, P.; Jiang, Y. Q.; Lin, C. M.; Hamel, E.; Long, B. H.; Fairchild, C. A.; Johnston, K. A. J. Med. Chem. 1998, 41, 3715-3726.
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J. Med. Chem.
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Kingston, D.G.I.1
Chaudhary, A.G.2
Chordia, M.D.3
Gharpure, M.4
Gunatilaka, A.A.L.5
Higgs, P.I.6
Rimoldi, J.M.7
Samala, L.8
Jagtap, P.G.9
Giannakakou, P.10
Jiang, Y.Q.11
Lin, C.M.12
Hamel, E.13
Long, B.H.14
Fairchild, C.A.15
Johnston, K.A.16
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