Synthesis and conformational analysis of (E)-9,10-dehydroepothilone B: A suggestive link between the chemistry and biology of epothilones Journal Article

  


Authors: Yoshimura, F.; Rivkin, A.; Gabarda, A. E.; Chou, T. C.; Dong, H.; Sukenick, G.; Morel, F. F.; Taylor, R. E.; Danishefsky, S. J.
Article Title: Synthesis and conformational analysis of (E)-9,10-dehydroepothilone B: A suggestive link between the chemistry and biology of epothilones
Abstract: The most potent epothilone analogue reported to date was obtained by incorporation of an E double bond at C9-C10 in the epothilone B series (see picture). Molecular modeling, NMR spectroscopic analysis, and chemical observations were used to rationalize the remarkable potency-enhancing effect of the double bond.
Keywords: controlled study; unclassified drug; drug activity; nonhuman; antineoplastic agents; antineoplastic agent; animal cell; mouse; animals; mice; animal experiment; animal model; antineoplastic activity; drug potency; drug structure; cell line, tumor; drug synthesis; time factors; mice, nude; tumor cell line; magnetic resonance spectroscopy; nuclear magnetic resonance spectroscopy; molecular structure; neoplasm transplantation; structure analysis; inhibitory concentration 50; infusions, intravenous; nuclear magnetic resonance; molecular conformation; synthesis (chemical); antitumor agents; structure-activity relationships; molecular model; epothilones; epothilone b; epothilone derivative; ketones; chemical bond; conformations; natural products; chemical bonds; spectroscopic analysis; article; conformational analysis; molecular modeling; 9,10 dehydroepothilone b
Journal Title: Angewandte Chemie - International Edition
Volume: 42
Issue: 22
ISSN: 1433-7851
Publisher: Wiley Blackwell  
Date Published: 2003-06-06
Start Page: 2518
End Page: 2521
Language: English
DOI: 10.1002/anie.200351407
PUBMED: 12800175
PROVIDER: scopus
DOI/URL:

http://www.scopus.com/inward/record.url?eid=2-s2.0-0038339582&partnerID=40&md5=297b6d5e93f2833ae68ccc09e4c1f011
Notes: Export Date: 12 September 2014 -- Source: Scopus
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MSK Authors
  1. Alexey Rivkin
    10 Rivkin
  2. Fumihiko Yoshimura
    7 Yoshimura
  3. Ana E Gabarda Ortega
    7 Gabarda Ortega
  4. Huajin Dong
    33 Dong
  5. Samuel J Danishefsky
    539 Danishefsky
  6. George D Sukenick
    23 Sukenick
  7. Ting-Chao Chou
    319 Chou
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