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Literature DB >> 26146360

The amido-pentadienoate-functionality of the rakicidins is a thiol reactive electrophile--development of a general synthetic strategy.

Lise L Clement¹, Michail Tsakos, Eva S Schaffert, Carsten Scavenius, Jan J Enghild, Thomas B Poulsen.

Abstract

We demonstrate that a unique class-defining functionality (mc-APD) found in macrocyclic natural products with potent anti-cancer activity, imparts these compounds with electrophilic reactivity. The mc-APD group represents an interesting structural hybrid between canonical biologically relevant Michael-acceptors. Further, a novel thiol-elimination method for preparation of the mc-APD group is outlined.

Entities: Chemical Disease

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Year: 2015 PMID： 26146360 DOI： 10.1039/c5cc04500b

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

2 in total

1. Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.

Authors: Paul A Jackson; John C Widen; Daniel A Harki; Kay M Brummond
Journal: J Med Chem Date: 2016-12-20 Impact factor: 7.446

2. Synthesis of ent-BE-43547A₁ reveals a potent hypoxia-selective anticancer agent and uncovers the biosynthetic origin of the APD-CLD natural products.

Authors: Nikolaj L Villadsen; Kristian M Jacobsen; Ulrik B Keiding; Esben T Weibel; Bjørn Christiansen; Thomas Vosegaard; Morten Bjerring; Frank Jensen; Mogens Johannsen; Thomas Tørring; Thomas B Poulsen
Journal: Nat Chem Date: 2016-11-21 Impact factor: 24.427

2 in total

The amido-pentadienoate-functionality of the rakicidins is a thiol reactive electrophile--development of a general synthetic strategy.

1. Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.

2. Synthesis of ent-BE-43547A1 reveals a potent hypoxia-selective anticancer agent and uncovers the biosynthetic origin of the APD-CLD natural products.

2. Synthesis of ent-BE-43547A₁ reveals a potent hypoxia-selective anticancer agent and uncovers the biosynthetic origin of the APD-CLD natural products.