Synthesis of Diacylhydrazine Derivatives Based on Tetrazole-Focused DNA-Encoded Library

Organic Letters, Journal Year: 2024, Volume and Issue: 26(5), P. 1094 - 1099

Published: Jan. 26, 2024

Utilizing already existing DNA-encoded libraries (DELs) for the generation of a distinct DEL represents an expedited strategy expanding chemical space. Herein, we leverage unique photoreactivity tetrazoles to synthesize diacylhydrazines on DNA. Widely available carboxylic acids serving as building blocks were employed under mild photomediated reaction conditions, affording diverse DNA-conjugated diacylhydrazines. This methodology also demonstrates robustness in DEL-compatible synthesis and facilitates preparation oligonucleotide-based probes.

Language: Английский

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Skeletal Editing of Benzene Motif: Photopromoted Transannulation for Synthesis of DNA-Encoded Seven-Membered Rings

Organic Letters, Journal Year: 2024, Volume and Issue: 26(11), P. 2212 - 2217

Published: March 7, 2024

In this report, we present a photopromoted, metal-free transannulation of phenyl azides for the synthesis DNA-encoded seven-membered rings. The transformation is efficiently achieved through skeletal editing strategy targeting benzene motif coupled with Reversible Adsorption to Solid Support (RASS) strategy. A variety valuable ring compounds, including 3H-azepines, azepinones, and unnatural amino acids, are now accessible. Crucially, DNA-compatible protocol can also be applied introduction complex molecules, as exemplified by Lorcaserin Betahistine. selective conversion readily available rings into high-value offers promising avenue construction diversified drug-like library.

Language: Английский

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On-DNA Three-Component Cycloaddition of Diazo Compounds, Nitrosoarenes, and Alkenes: Syntheses of Isoxazolidines for DNA-Encoded Chemical Libraries

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

A DNA-compatible three-component reaction is disclosed for the synthesis of on-DNA polysubstituted isoxazolidines that serve as privileged core scaffolds in numerous natural products and bioactive molecules. This one-pot approach involves 1,3-dipolar cycloaddition DNA-tagged styrenes with diazo compounds nitrosoarenes an aqueous solution KOAc. The demonstrates excellent functional group compatibility, providing a conventional protocol construction DNA-labeled isoxazolidine library.

Language: Английский

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Hydrophobic Surfactant–DNA Complex (Surf-DNA) Enables DNA-Encoded-Library-Compatible Decarboxylative Arylation under Anhydrous Conditions

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4365 - 4370

Published: May 14, 2024

DNA-encoded libraries (DELs) are a key technology for identifying small-molecule hits in both the pharmaceutical industry and academia, but their chemical diversity is largely limited to water-compatible reactions aid solubility integrity of encoding DNA tags. To broaden DEL space, we present workflow utilizing DNA-cationic surfactant complexation that enables dissolution on-DNA anhydrous organic solvents. We demonstrate its utility by developing DEL-compatible photoredox decarboxylative C(sp

Language: Английский

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Visible-light-promoted one-pot synthesis of β-keto sulfones from aryldiazo tetrafluoroborate salts via aerobic multicomponent reaction

Tetrahedron, Journal Year: 2024, Volume and Issue: 167, P. 134303 - 134303

Published: Oct. 10, 2024

Language: Английский

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