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Literature DB >> 22849854

Biomimetic semisynthesis of arglabin from parthenolide.

Jia-Dai Zhai¹, Dongmei Li, Jing Long, Hao-Liang Zhang, Jian-Ping Lin, Chuan-Jiang Qiu, Quan Zhang, Yue Chen.

Abstract

The semisynthesis of arglabin, an anticancer drug in clinical application, is developed from abundant natural product parthenolide via three steps. Each step in this sequence is highly stereoselective, and the substrate-dependent stereoselectivity in the epoxidation step can be explained by computational calculations. The success of chemical semisynthesis of arglabin suggests that the biosynthesis of arglabin might proceed in a similar pathway.

Entities: Chemical

Mesh：

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Year: 2012 PMID： 22849854 DOI： 10.1021/jo300888s

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

17 in total

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2. Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae.

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Biomimetic semisynthesis of arglabin from parthenolide.

1. Micheliolide, a new sesquiterpene lactone that inhibits intestinal inflammation and colitis-associated cancer.

2. Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae.

3. Indole carboxylic acid esters of melampomagnolide B are potent anticancer agents against both hematological and solid tumor cells.

4. Scalable, enantioselective synthesis of germacrenes and related sesquiterpenes inspired by terpene cyclase phase logic.

5. LiCl-promoted amination of β-methoxy amides (γ-lactones).

6. A molecular electron density theory study of the mechanism, chemo- and stereoselectivity of the epoxidation reaction of R-carvone with peracetic acid.

7. Micheliolide derivative DMAMCL inhibits glioma cell growth in vitro and in vivo.

8. Micheliolide suppresses LPS-induced neuroinflammatory responses.

9. Acid-Induced Rearrangement of Epoxygermacranolides: Synthesis of Furanoheliangolides and Cadinanes from Nobilin.

10. Antineoplastic effects and mechanisms of micheliolide in acute myelogenous leukemia stem cells.