Synthesis of psymberin analogues: Probing a functional correlation with the pederin/mycalamide family of natural products

Organic Letters

Volumn 9, Issue 2, 2007, Pages 227-230

  Jiang, Xin ^a   Williams, Noelle ^a   De Brabander, Jef K ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MYCALAMIDE A; MYCALAMIDE B; PEDERIN; PSYMBERIN; PSYMPEDERIN; PYRAN DERIVATIVE; PYRONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECT; DRUG SCREENING; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SENSITIVITY AND SPECIFICITY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRANS; PYRONES; SENSITIVITY AND SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33846589318     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062656o     Document Type: Article

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35. There is conformational flexibility in the acyclic C1-C6 and C14-C16 fragments. The conformations in Figure 3 are meant to illustrate the proximity of these two fragments as observed by NOE interactions-between H5 and C15/C16-OMe protons. For a complete listing of chemical shifts, coupling constants, and NOE correlations, and copies of corresponding spectra, see the Supporting Information.
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37. Interestingly, analogue 19 is equipotent to C8-epi- psymberin 5 and about three-fold more potent than 18 against the PC3 pancreatic tumor cell line.