Solid-Phase Synthesis of Tetramic Acid via Resin-Bound Enol Ethers as a Privileged Scaffold in Drug Discovery

2018 ◽  
Vol 360 (19) ◽  
pp. 3693-3699 ◽  
Author(s):  
Eva Schütznerová ◽  
Allen G. Oliver ◽  
Adam Přibylka ◽  
Viktor Krchňák
Keyword(s):  
Drug Discovery ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Tetramic Acid ◽  
Enol Ethers ◽  
Phase Synthesis ◽  
Privileged Scaffold

scholarly journals Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1406 ◽  
Author(s):  
Eva Schütznerová ◽  
Anna Krchňáková ◽  
Viktor Krchňák
Keyword(s):  
Natural Products ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Tetramic Acid ◽  
Enol Ethers ◽  
Phase Synthesis ◽  
Wang Resin ◽  
Synthetic Strategy ◽  
Solid Phase Organic Synthesis ◽  
Acid Labile

In solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the solid-phase synthesis of pyrrolidine-2,4-diones, which represent the core structure of several natural products, including tetramic acid. Base-triggered condensation of pyrrolidine-2,4-diones yielded 4-hydroxy-1,1′,2′,5-tetrahydro-2H,5′H-[3,3′-bipyrrole]-2,5′-diones.

Solid-Phase Traceless Synthesis of Selected Nitrogen-Containing Heterocyclic Compounds. The Encore Technique for Directed Sorting of Modular Solid Support

2001 ◽  
Vol 66 (7) ◽  
pp. 1078-1106 ◽  
Author(s):  
Viktor Krchňák ◽  
Jennifer Smith ◽  
Josef Vágner
Keyword(s):  
Drug Discovery ◽  
Hydrogen Atom ◽  
Heterocyclic Compounds ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Support ◽  
Combinatorial Synthesis ◽  
Target Compound ◽  
Phase Synthesis ◽  
Acidic Reagent

The acid lability of electron-rich N-benzylanilines has been exploited in a linker for the traceless solid-phase synthesis of benzimidazoles, 2-aminobenzimidazoles, quinoxalinones and tetrahydroquinoxalines. The target compound precursors were assembled on a solid-phase support derivatized with either a benzylamine or a benzhydrylamine linker. Exposure to an acidic reagent caused cleavage of the C(benzyl)-N(aniline) bond, releasing the product with only a hydrogen atom on the descending nitrogen. The Encore technique for directed sorting on SynPhase Lanterns has been developed and applied to combinatorial synthesis of generic drug discovery libraries.

Tentoxin as a Scaffold for Drug Discovery. Total Solid-Phase Synthesis of Tentoxin and a Library of Analogues

2003 ◽  
Vol 5 (12) ◽  
pp. 2115-2118 ◽  
Author(s):  
Jose C. Jiménez ◽  
Bibiana Chavarría ◽  
Àngel López-Macià ◽  
Miriam Royo ◽  
Ernest Giralt ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Total Solid ◽  
Phase Synthesis

A facile solid phase synthesis of tetramic acid

2003 ◽  
Vol 13 (15) ◽  
pp. 2505-2507 ◽  
Author(s):  
Zhanxiang Liu ◽  
Xiuxiu Ruan ◽  
Xian Huang
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Tetramic Acid ◽  
Phase Synthesis

scholarly journals Solid-Phase Synthesis of Arylpiperazine Derivatives and Implementation of the Distributed Drug Discovery (D3) Project in the Search for CNS Agents

Molecules ◽  
2011 ◽  
Vol 16 (5) ◽  
pp. 4104-4121 ◽  
Author(s):  
Paweł Zajdel ◽  
Joanna Król ◽  
Katarzyna Grychowska ◽  
Maciej Pawłowski ◽  
Gilles Subra ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis
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