12,13-Isotaxanes: Synthesis of new potent analogs and X-ray crystallographic confirmation of structure

Journal of Medicinal Chemistry

Volumn 40, Issue 18, 1997, Pages 2810-2812

  Johnson, Roy A ^a   Dobrowolski, Paul J ^a   Nidy, Eldon G ^a   Gebhard, Ilse ^a   Qualls, Samuel J ^a   Wicnienski, Nancy A ^a   Kelly, Robert C ^a   Pitts, Thomas W ^a   Lopes, Narima M ^a   DeKoning, Thomas F ^a   Mattern, Sally J ^a   Weed, Sheldon D ^a   McGovren, J Patrick ^a   Chidester, Constance G ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACCATIN III; DOCETAXEL; DRUG VEHICLE; PACLITAXEL; PACLITAXEL DERIVATIVE; TAXANE DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; CANCER INHIBITION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INTRAVENOUS DRUG ADMINISTRATION; LETTER; MELANOMA CELL; MITOSIS INHIBITION; MOUSE; NONHUMAN; OVARY CARCINOMA; STRUCTURE ACTIVITY RELATION; SURVIVAL TIME; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; ANIMALS; ANTINEOPLASTIC AGENTS; BRIDGED COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; FEMALE; HUMANS; MELANOMA, EXPERIMENTAL; MICE; MICE, INBRED STRAINS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OVARIAN NEOPLASMS; PACLITAXEL; TAXOIDS; TUMOR CELLS, CULTURED;

EID: 15144348920     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9703350     Document Type: Letter

References (18)

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2. The name taxol has been registered as a trademark by Bristol-Myers Squibb; the generic name for taxol is paclitaxel.
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4. 7α-Fluorotaxol has been described by: Chen, S.-H.; Huang, S.; Farina, V. On the Reaction of Taxol with DAST. Tetrahedron Lett. 1994, 35, 41-44.
5. Cyclopropane formation in taxanes has also been described by: (a) Chen, S.-H.; Huang, S.; Wei, J.; Farina, V. Serendipitous Synthesis of a Cyclopropane-Containing Taxol Analog via Anchimeric Participation of an Unactivated Angular Methyl Group. J. Org. Chem. 1993, 58, 4520-4521. See also ref 4. (b) Klein, L. L.; Maring, C. J.; Li, L.; Yeung, C. M.; Thomas, S. A.; Grampovnik, D. J.; Plattner, J. J.; Henry, R. F. Synthesis of Ring B-Rearranged Taxane Analogs. J. Org. Chem. 1994, 59, 2370-2373. (c) Bouchard, H.; Pulicani, J.-P.; Vuilhorgne, M.; Bourzat, J.-D.; Commerçon, A. Improved Acess to 19-Nor-7β,8β-Methylene Taxoids and Formation of a 7-Membered C-Ring Analog of Docetaxel by Electrochemistry. Tetrahedron Lett. 1994, 35, 9713-9716.
6. Cyclopropane formation in taxanes has also been described by: (a) Chen, S.-H.; Huang, S.; Wei, J.; Farina, V. Serendipitous Synthesis of a Cyclopropane-Containing Taxol Analog via Anchimeric Participation of an Unactivated Angular Methyl Group. J. Org. Chem. 1993, 58, 4520-4521. See also ref 4. (b) Klein, L. L.; Maring, C. J.; Li, L.; Yeung, C. M.; Thomas, S. A.; Grampovnik, D. J.; Plattner, J. J.; Henry, R. F. Synthesis of Ring B-Rearranged Taxane Analogs. J. Org. Chem. 1994, 59, 2370-2373. (c) Bouchard, H.; Pulicani, J.-P.; Vuilhorgne, M.; Bourzat, J.-D.; Commerçon, A. Improved Acess to 19-Nor-7β,8β-Methylene Taxoids and Formation of a 7-Membered C-Ring Analog of Docetaxel by Electrochemistry. Tetrahedron Lett. 1994, 35, 9713-9716.
7. Cyclopropane formation in taxanes has also been described by: (a) Chen, S.-H.; Huang, S.; Wei, J.; Farina, V. Serendipitous Synthesis of a Cyclopropane-Containing Taxol Analog via Anchimeric Participation of an Unactivated Angular Methyl Group. J. Org. Chem. 1993, 58, 4520-4521. See also ref 4. (b) Klein, L. L.; Maring, C. J.; Li, L.; Yeung, C. M.; Thomas, S. A.; Grampovnik, D. J.; Plattner, J. J.; Henry, R. F. Synthesis of Ring B-Rearranged Taxane Analogs. J. Org. Chem. 1994, 59, 2370-2373. (c) Bouchard, H.; Pulicani, J.-P.; Vuilhorgne, M.; Bourzat, J.-D.; Commerçon, A. Improved Acess to 19-Nor-7β,8β-Methylene Taxoids and Formation of a 7-Membered C-Ring Analog of Docetaxel by Electrochemistry. Tetrahedron Lett. 1994, 35, 9713-9716.
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