Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition

Andrews SP; Ball M; Wierschem F; Cleator E; Oliver S; Hogenauer K; Simic O; Antonello A; Hunger U; Smith MD

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Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition

机译：五种毒胡萝卜素的总合成：瓜亚诺利德天然产物表现出亚纳摩尔SERCA抑制作用

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Herein we describe the total synthesis of five guaianolide natural products: thapsigargin, thapsivillosin C, thapsivillosin F, trilobolide and nortrilobolide. Prodrug derivatives of thapsigargin have shown selective in vivo cytotoxicity against prostate tumours and the need for of this phenomenon highlights the importance of these total syntheses. The first absolute stereochemical assignment of thapsivillosin C is also delineated.

机译：在这里，我们描述了五种愈创木酚内酯天然产物的总合成：thapsigargin，thapsivillosin C，thapsivillosin F，trilobolide和nortrilobolide。毒胡萝卜素的前药衍生物已经显示出对前列腺肿瘤的选择性体内细胞毒性，并且对该现象的需要突出了这些总合成的重要性。还描述了毒胡萝卜素C的第一个绝对立体化学分配。

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来源
《Chemistry: A European journal》 |2007年第20期|共25页
作者
Andrews SP; Ball M; Wierschem F; Cleator E; Oliver S; Hogenauer K; Simic O; Antonello A; Hunger U; Smith MD;
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正文语种 eng
中图分类化学;
关键词
guaianolide; natural products; sesquiterpene; thapsigargin; total synthesis; SARCOPLASMIC-RETICULUM CA2+-ATPASE; LIBERATING SESQUITERPENE LACTONES; PROSTATIC-CANCER CELLS; THAPSIA-GARGANICA L; CALCIUM-PUMP; ASYMMETRIC DIHYDROXYLATION; OLEFIN METATHESIS; OSMIUM-TETROXIDE; BINDING-SITE; MECHANISM;

机译：愈创木酚内酯;天然产物;倍半萜烯;thapsigargin;全合成;SARCOPLASMIC-RETICULUM CA2 + -ATPase;解放性倍半萜内酯;前列腺癌细胞;THAPSIA-GARGANICA L;钙-泵浦;不对称二羟甲基化;异丁烯二酸化;机制;

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专利

1. Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition [J] . Andrews SP, Ball M, Wierschem F, Chemistry: A European journal . 2007,第20期

机译：五种毒胡萝卜素的总合成：瓜亚诺利德天然产物表现出亚纳摩尔SERCA抑制作用
2. Design and total synthesis of unnatural analogues of the sub-nanomolar SERCA inhibitor thapsigargin [J] . Stephen P. Andrews, Malcolm M. Tait, Matthew Ball, Organic & biomolecular chemistry . 2007,第9期

机译：亚纳摩尔SERCA抑制剂毒胡萝卜素的非天然类似物的设计和全合成
3. First total synthesis of (+)-broussonetine W: glycosidase inhibition of natural product b analogs [J] . Ying-Ying Song, Kyoko Kinami, Atsushi Kato, Organic & biomolecular chemistry . 2016,第22期

机译：首次全合成（+）-布罗西汀W：抑制天然产物b类似物的糖苷酶
4. Stereoselective synthesis of 2,2-substituted chromans: Towards the total synthesis of natural products. [C] . Gloria Hernandez-Torres, Mercedes Lecea, Antonio Urbano European Symposium on Organic Chemistry . 2009

机译：2,2取代染色体的立体选择性合成：朝向天然产物的总合成。
5. Diastereoselective strategies for the synthesis of glutamate-containing natural products: Total synthesis of (S)-(+)-lycoperdic acid and studies toward the total synthesis of (-)-dysiherbaine and the design and synthesis of a scaffold for glutamate receptor ligands using a natural product-based library approach. [D] . Cohen, Jamie Lisa. 2006

机译：合成含谷氨酸天然产物的非对映选择性策略：（S）-（+）-乙二酸的全合成，以及对（-）-dysiherbaine的全合成以及使用谷氨酸受体配体的支架设计和合成的研究基于自然产品的图书馆方法。
6. Natural Product Synthesis Special Feature: Synthesis of the thapsigargins [O] . Steven V. Ley, Alessandra Antonello, Emily P. Balskus, 2004

机译：天然产物合成的特殊功能：毒胡萝卜素的合成
7. Cover Picture: Total Synthesis of Five Thapsigargins: Guaianolide Natural Products Exhibiting Sub-Nanomolar SERCA Inhibition (Chem. Eur. J. 20/2007) [O] . Stephen P. Andrews, Matthew Ball, Frank Wierschem, 2007

机译：封面图片：五个Thapigargins的总合成：愈冠醇天然产品，展示亚摩尔塞尔塞菌抑制（Chem。欧元。J.20 / 2007）

Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition

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