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

Organic Letters, Год журнала: 2024, Номер 26(5), С. 1094 - 1099

Опубликована: Янв. 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.

Язык: Английский

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DNA-compatible functional group transformations via K₂RuO₄-mediated oxidation

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(10), С. 2851 - 2856

Опубликована: Янв. 1, 2024

K 2 RuO 4 -mediated oxidation offers a DNA-compatible method for functional group transformations, enabling alcohol-to-carboxylic acid and amine-to-nitrile conversions valuable DNA-encoded library synthesis.

Язык: Английский

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Using DNA-encoded libraries of fragments for hit discovery of challenging therapeutic targets

Expert Opinion on Drug Discovery, Год журнала: 2024, Номер 19(6), С. 725 - 740

Опубликована: Май 16, 2024

Introduction The effectiveness of Fragment-based drug design (FBDD) for targeting challenging therapeutic targets has been hindered by two factors: the small library size and complexity fragment-to-hit optimization process. DNA-encoded (DEL) technology offers a compelling robust high-throughput selection approach to potentially address these limitations.

Язык: Английский

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On-DNA Medicinal Chemistry: Focused Libraries, Fragment Expansion, and Hit Optimisation

Royal Society of Chemistry eBooks, Год журнала: 2025, Номер unknown, С. 87 - 118

Опубликована: Фев. 21, 2025

Since their inception thirty years ago, DNA-encoded libraries (DELs) have proven to be a formidable technique for naïve hit finding, with implementation facilitating the generation of lead-series across wide range target classes. In recent however, it has been demonstrated that utility DELs within drug discovery need not restricted this purpose, variety strategies being adopted broaden impact encoded field. Discussed herein are current applications wider medicinal chemistry pipeline, including application and focused libraries; use fragment expansion; potential facilitation optimisation processes. The state field is assessed, future directions technology area explored.

Язык: Английский

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Late-Stage Functionalization Strategies of 1,2,3-Triazoles: A Post-Click Approach in Organic Synthesis

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 18, 2025

The 1,2,3-triazole scaffolds are an important class of biologically privileged heterocyclic compounds with several key applications in chemistry, biology, medicine, agriculture, and material science. "postclick" functionalization 1,2,3-triazoles may emerge as a promising tactic for the construction molecular architectures therapeutics is considered to be growing area investigation. This interest extends beyond regioselective Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) method that involves trapping Cu(I)-triazole suitable precursors. In this Perspective, we highlight impact postclick strategies organic synthesis required late-stage hope emerging concept provide ample opportunities modern notable medicinal materials

Язык: Английский

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Synthesis of 5-(Aryl)amino-1,2,3-triazole-containing 2,1,3-Benzothiadiazoles via Azide–Nitrile Cycloaddition Followed by Buchwald–Hartwig Reaction

Molecules, Год журнала: 2024, Номер 29(9), С. 2151 - 2151

Опубликована: Май 6, 2024

An efficient access to the novel 5-(aryl)amino-1,2,3-triazole-containing 2,1,3-benzothiadiazole derivatives has been developed. The method is based on 1,3-dipolar azide–nitrile cycloaddition followed by Buchwald–Hartwig cross-coupling afford corresponding N-aryl and N,N-diaryl substituted 5-amino-1,2,3-triazolyl 2,1,3-benzothiadiazoles under NHC-Pd catalysis. one-pot diarylative Pd-catalyzed heterocyclization opens straightforward route triazole-linked carbazole-benzothiadiazole D-A systems. optical electrochemical properties of compound obtained were investigated estimate their potential application as emissive layers in OLED devises. quantum yield photoluminescence (PLQY) synthesized depends a large extent electron-donating strengths donor (D) component, reaching some cases values closed 100%. Based most photoactive derivative wide bandgap host material mCP, light-emitting layer was made. device showed maximum brightness 8000 cd/m2 at an applied voltage 18 V. current efficiency reaches value 3.29 cd/A.

Язык: Английский

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Synthesis of Thiohydantoin Scaffolds on DNA for Focused DNA-Encoded Library Construction

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 3, 2024

Thiohydantoin represents a significant class of biologically active privileged heterocyclic scaffolds. Herein, we present convenient and robust DNA-compatible method for constructing thiohydantoin-focused DNA-encoded library. This reaction can be applied to wide variety isothiocyanate partners, arylamine feedstocks, diverse α-amine acid derivatives, exhibiting excellent conversions, high functional group tolerance, preservation DNA tag integrity. Our allows easy access valuable three-cycle

Язык: Английский

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DNA‐Compatible Nitriles Hydrolysis for Late‐Stage Functionalization of DNA‐Encoded Libraries

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(11)

Опубликована: Авг. 26, 2024

Abstract Primary amides play a crucial role in organic and pharmaceutical synthesis. Herein, we present rapid convenient method for transforming diverse DNA‐conjugated nitriles into primary utilizing hydrogen peroxide potassium carbonate. The substrate scope DEL compatibility of this reaction were thoroughly investigated, revealing wide range substrates with moderate‐to‐excellent conversion. This on‐DNA transformation holds significant promise constructing DNA‐encoded libraries (DELs) enabling late‐stage functionalization to expand chemical diversity. Our approach not only highlights the versatility but also underscores its potential broad applications

Язык: Английский

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Synthetic Strategies for C‐Amino 1,2,3‐Triazoles and Their Oxides: A Review

Journal of Heterocyclic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 12, 2024

ABSTRACT The review is devoted to synthetic methods for the preparation of C ‐amino 1,2,3‐triazoles and their oxides being important precursors in development energetic compounds as well biological, medicinal, organic, bio‐organic, polymer, material chemistry. This research mainly covers papers published after year 1986.

Язык: Английский

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Five-membered ring systems: With more than 1 N atom

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 211 - 257

Опубликована: Янв. 1, 2024

Язык: Английский

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