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扁枝石松生物碱类似物的合成:探究与多节扁贝素/海绵酰胺类天然产物的功能相关性

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

作者信息

Jiang Xin, Williams Noelle, De Brabander Jef K

机构信息

Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, USA.

出版信息

Org Lett. 2007 Jan 18;9(2):227-30. doi: 10.1021/ol062656o.

Abstract

In this letter we describe an efficient synthesis of "psympederin", a hybrid between the novel antitumor natural product psymberin and the blister beetle toxin pederin. Evaluation of antiproliferative activity reveals that the dihydroisocoumarin fragment is important for psymberin toxicity and the cyclic pederate fragment is important for pederin/mycalamide toxicity. On the basis of preliminary results described herein, we speculate that, despite their structural resemblance, psymberin and pederin/mycalamide induce toxicity through different mechanisms. [reaction: see text].

摘要

在本信函中,我们描述了“psympederin”的高效合成方法,它是新型抗肿瘤天然产物psymberin与斑蝥毒素pederin的杂合物。对其抗增殖活性的评估表明,二氢异香豆素片段对psymberin的毒性很重要,而环状pederate片段对pederin/mycalamide的毒性很重要。基于本文所述的初步结果,我们推测,尽管psymberin和pederin/mycalamide在结构上相似,但它们通过不同的机制诱导毒性。[反应:见正文]

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本文引用的文献

1
Total synthesis of (+)-mycalamide A.(+)-麦卡酰胺A的全合成。
Org Lett. 2006 Mar 2;8(5):875-8. doi: 10.1021/ol052943c.
5
Configuration of the psymberin amide side chain.psymberin酰胺侧链的构型。
Org Lett. 2005 Jul 7;7(14):2905-8. doi: 10.1021/ol0508375.
6
Total synthesis of mycalamide A.麦卡酰胺A的全合成。
J Am Chem Soc. 2005 May 25;127(20):7290-1. doi: 10.1021/ja050728l.
10
A formal synthesis of (-)-mycalamide A.(-)-麦卡酰胺A的形式合成。
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