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Oxazole‐Bridged Combretastatin A Analogues with Improved Anticancer Properties
Author(s) -
Biersack Bernhard,
Effenberger Katharina,
Schobert Rainer,
Ocker Matthias
Publication year - 2010
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200900477
Subject(s) - oxazole , chemistry , combretastatin , potency , stereochemistry , cell cycle checkpoint , downregulation and upregulation , cell cycle , cancer research , in vitro , cell , biochemistry , medicine , tubulin , biology , microtubule , gene , microbiology and biotechnology
Three new oxazole‐bridged combretastatin A analogues with additional functional groups at the B‐ring [‐SMe, ‐OH, p ‐quinone] were tested for antiproliferative activity and specificity on human HL‐60 leukemia, 518A2 melanoma, and colon carcinomas HCT‐116 (wt)/(p53 −/− ) and HT‐29 cells. While all oxazoles, except quinone 8 , were efficacious against HCT‐116 cells at submicromolar IC 50 values (48 h incubation), only thioanisole 5 achieved this potency in combretastatin‐refractory HT‐29 cells by significant upregulation of p21 cip1/waf1 associated with an S/G 2 cell‐cycle arrest.