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Title: Synthesis, structural characterisation, and preliminary evaluation of non-indolin-2-one-based angiogenesis inhibitors related to sunitinib (Sutent®)
Authors: Pichit Sudta
Nicholas Kirk
Anna Bezos
Anthony Gurlica
Rhys Mitchell
Thomas Weber
Anthony C. Willis
Samran Prabpai
Palangpon Kongsaeree
Christopher R. Parish
Sunit Suksamrarn
Michael J. Kelso
Srinakharinwirot University
University of Wollongong
Australian National University
Mahidol University
Keywords: Chemistry
Issue Date: 27-Aug-2013
Citation: Australian Journal of Chemistry. Vol.66, No.8 (2013), 864-873
Abstract: The indolin-2-one fused-ring system and the 2,4-dimethylpyrrole unit represent key structural motifs in the anticancer drug sunitinib (Sutent®) and predecessor angiogenesis inhibitors that have undergone anticancer clinical trials (e.g. semaxanib, SU5416). In pursuit of novel anti-angiogenic scaffolds, we were interested in identifying whether the indolin-2-one group in these structures could be modified without losing activity. This paper describes novel condensation chemistry used to prepare a test series of (E)-and (Z)-alkenes related to SU5416 that retain the 2,4-dimethylpyrrole unit while incorporating ring-opened indolin-2-ones. Unique structural characteristics were identified in the compounds, such as intramolecular hydrogen bonds in the (Z)-alkenes, and several examples were shown to possess significant anti-angiogenic activity in a rat aorta in vitro model of angiogenesis. The work demonstrates that the indolin-2-one moiety is not an absolute requirement for angiogenesis inhibition in the sunitinib/SU5416 class. © 2013 CSIRO.
ISSN: 14450038
Appears in Collections:Scopus 2011-2015

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