氯绿菌素、其七种发色团非对映异构体及关键类似物的评估
Evaluation of Chlorofusin, its Seven Chromophore Diastereomers, and Key Analogues.
作者信息
Clark Ryan C, Lee Sang Yeul, Hwang Inkyu, Searcey Mark, Boger Dale L
机构信息
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, USA.
出版信息
Tetrahedron Lett. 2009 Jul 1;50(26):3151-3153. doi: 10.1016/j.tetlet.2009.01.081.
Abstract
Chlorofusin, its seven chromophore diastereomers, and key analogues were comparatively examined for inhibition of MDM2-p53 binding revealing that the chromophore, but not simple replacements, contributes significantly to the natural products properties, and that this contribution is independent of its relative and absolute stereochemistry.
摘要
对氯富辛及其七种发色团非对映异构体和关键类似物进行了抑制MDM2-p53结合的比较研究，结果表明，发色团而非简单的取代基对天然产物的性质有显著贡献，且这种贡献与其相对和绝对立体化学无关。
相似文献
1
Evaluation of Chlorofusin, its Seven Chromophore Diastereomers, and Key Analogues.
Tetrahedron Lett. 2009 Jul 1;50(26):3151-3153. doi: 10.1016/j.tetlet.2009.01.081.
2
Total synthesis of chlorofusin, its seven chromophore diastereomers, and key partial structures.
J Am Chem Soc. 2008 Sep 17;130(37):12355-69. doi: 10.1021/ja8012819. Epub 2008 Aug 20.
3
The isolation, total synthesis and structure elucidation of chlorofusin, a natural product inhibitor of the p53-mDM2 protein-protein interaction.
Nat Prod Rep. 2009 Apr;26(4):465-77. doi: 10.1039/b821676b.
4
Identification of a new p53/MDM2 inhibitor motif inspired by studies of chlorofusin.
Bioorg Med Chem Lett. 2015 Nov 1;25(21):4878-4880. doi: 10.1016/j.bmcl.2015.06.014. Epub 2015 Jun 14.
5
Synthesis of the chlorofusin cyclic peptide: assignment of the asparagine stereochemistry.
Org Lett. 2003 Dec 25;5(26):5047-50. doi: 10.1021/ol036083g.
6
Solid-phase synthesis of the cyclic peptide portion of chlorofusin, an inhibitor of p53-MDM2 interactions.
Org Lett. 2003 Dec 25;5(26):5051-4. doi: 10.1021/ol0360849.
7
Solid-phase synthesis of chlorofusin analogues.
J Org Chem. 2007 Jul 6;72(14):5146-51. doi: 10.1021/jo070450a. Epub 2007 Jun 9.
8
Total synthesis and evaluation of cytostatin, its C10-C11 diastereomers, and additional key analogues: impact on PP2A inhibition.
J Am Chem Soc. 2006 Dec 27;128(51):16720-32. doi: 10.1021/ja066477d.
9
Synthesis of the Chlorofusin Cyclic Peptide.
Tetrahedron. 2009;65(16):3281-3284. doi: 10.1016/j.tet.2008.09.029.
10
Isolation and structure elucidation of Chlorofusin, a novel p53-MDM2 antagonist from a Fusarium sp.
J Am Chem Soc. 2001 Jan 31;123(4):554-60. doi: 10.1021/ja002940p.
引用本文的文献
1
Natural product MDM2 inhibitors: anticancer activity and mechanisms of action.
Curr Med Chem. 2012;19(33):5705-25. doi: 10.2174/092986712803988910.
2
Pharmacological targets in the ubiquitin system offer new ways of treating cancer, neurodegenerative disorders and infectious diseases.
Expert Rev Mol Med. 2011 Nov 17;13:e35. doi: 10.1017/S1462399411002031.
本文引用的文献
1
Synthesis of the Chlorofusin Cyclic Peptide.
Tetrahedron. 2009;65(16):3281-3284. doi: 10.1016/j.tet.2008.09.029.
2
The isolation, total synthesis and structure elucidation of chlorofusin, a natural product inhibitor of the p53-mDM2 protein-protein interaction.
Nat Prod Rep. 2009 Apr;26(4):465-77. doi: 10.1039/b821676b.
3
Total synthesis of chlorofusin, its seven chromophore diastereomers, and key partial structures.
J Am Chem Soc. 2008 Sep 17;130(37):12355-69. doi: 10.1021/ja8012819. Epub 2008 Aug 20.
4
Total synthesis, stereochemical reassignment, and absolute configuration of chlorofusin.
J Am Chem Soc. 2007 Aug 15;129(32):9860-1. doi: 10.1021/ja073264v. Epub 2007 Jul 19.
5
Solid-phase synthesis of chlorofusin analogues.
J Org Chem. 2007 Jul 6;72(14):5146-51. doi: 10.1021/jo070450a. Epub 2007 Jun 9.
6
Total synthesis, assignment of absolute stereochemistry, and structural revision of chlorofusin.
J Am Chem Soc. 2007 May 23;129(20):6400-1. doi: 10.1021/ja072225g. Epub 2007 May 2.
7
Small-molecule inhibitors of the p53 suppressor HDM2: have protein-protein interactions come of age as drug targets?
Trends Pharmacol Sci. 2004 Jul;25(7):343-6. doi: 10.1016/j.tips.2004.04.011.
8
Solid-phase synthesis of the cyclic peptide portion of chlorofusin, an inhibitor of p53-MDM2 interactions.
Org Lett. 2003 Dec 25;5(26):5051-4. doi: 10.1021/ol0360849.
9
Synthesis of the chlorofusin cyclic peptide: assignment of the asparagine stereochemistry.
Org Lett. 2003 Dec 25;5(26):5047-50. doi: 10.1021/ol036083g.
10
Identification and prediction of promiscuous aggregating inhibitors among known drugs.
J Med Chem. 2003 Oct 9;46(21):4477-86. doi: 10.1021/jm030191r.
Zotero 插件