喜树碱螺缩酮结构和立体化学要求的抗增殖活性。
Structural and stereochemical requirements of the spiroketal group of hippuristanol for antiproliferative activity.
机构信息
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032 Shanghai, China.
出版信息
Bioorg Med Chem Lett. 2010 May 15;20(10):3112-5. doi: 10.1016/j.bmcl.2010.03.093. Epub 2010 Mar 30.
Abstract
Hippuristanol is a natural product that has recently been shown to inhibit eukaryotic translation initiation and tumor cell proliferation. To investigate the structure and activity relationship of hippuristanol, we synthesized a series of analogs by expanding the size of its F ring and determined their effects on the proliferation of cancer cell lines. All changes to the F-ring of hippuristanol resulted in 3-fold to >100-fold decrease in activity.
摘要
六氢鸭嘴花碱是一种天然产物，最近的研究表明其可以抑制真核起始翻译和肿瘤细胞增殖。为了研究六氢鸭嘴花碱的结构和活性关系，我们通过扩大其 F 环的大小合成了一系列类似物，并测定了它们对癌细胞系增殖的影响。六氢鸭嘴花碱 F 环的所有变化都导致活性降低 3 倍至 >100 倍。
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1
Expeditious synthesis of hippuristanol and congeners with potent antiproliferative activities.
Chemistry. 2009 Oct 12;15(40):10356-9. doi: 10.1002/chem.200901732.
2
Selective pharmacological targeting of a DEAD box RNA helicase.
PLoS One. 2008 Feb 13;3(2):e1583. doi: 10.1371/journal.pone.0001583.
3
Stopping trouble before it starts.
ACS Chem Biol. 2006 Feb 17;1(1):17-9. doi: 10.1021/cb0600029.
4
Small molecule derails translation initiation.
Nat Chem Biol. 2006 Apr;2(4):176-7. doi: 10.1038/nchembio0406-176.
5
Functional characterization of IRESes by an inhibitor of the RNA helicase eIF4A.
Nat Chem Biol. 2006 Apr;2(4):213-20. doi: 10.1038/nchembio776. Epub 2006 Mar 12.
6
Inhibition of eukaryotic translation initiation by the marine natural product pateamine A.
Mol Cell. 2005 Dec 9;20(5):709-22. doi: 10.1016/j.molcel.2005.10.008.
7
Stimulation of mammalian translation initiation factor eIF4A activity by a small molecule inhibitor of eukaryotic translation.
Proc Natl Acad Sci U S A. 2005 Jul 26;102(30):10460-5. doi: 10.1073/pnas.0504249102. Epub 2005 Jul 19.
8
Stereoselective synthesis and structure of butalactin and lactone II isolated from Streptomyces species.
Org Biomol Chem. 2004 Oct 7;2(19):2777-85. doi: 10.1039/B407820A. Epub 2004 Aug 23.
9
Novel synthesis of cholesterol analogs: condensation of pregnenolone with dihydropyran or dihydrofuran.
Steroids. 1991 Sep;56(9):458-63. doi: 10.1016/0039-128x(91)90001-c.
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