Photoinduced Regioselective Sulfonylsulfination of Alkenes

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(5), P. 3664 - 3674

Published: Feb. 21, 2024

Regioselective 1,2-dichalcogenation of alkenes has attracted significant attention in modern organic synthetic chemistry. While there are a plethora methods to access alkene dichalcogenated architectures, sulfonylsulfination is extremely challenging due the inherent characteristics sulfur atom. Herein, multicomponent fragment coupling alkenes, sulfinates, and DABSO was developed construct densely functionalized sulfonylsulfinated products, which otherwise access, with broad substrate scope group tolerance under mild operationally simple conditions, using an inexpensive 100–1000 ppm photocatalyst. In addition, protocol applied late-stage functionalization complex molecules, obtained products were converted into diverse downstream transformations demonstrate their potential. Experimental theoretical mechanistic investigations suggest that these reactions proceed through sequential sulfonyl sulfinyl oxygen radical mutual radical–polar crossover coupling. This strategy provides previously inaccessible good-to-high regio- stereoselectivity, along opening up unexplored directions.

Language: Английский

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Insecticidal Evaluation, Molecular Docking, and Structure-Activity Relationship Study of Some Synthesized Thiazole-Owing Hydrazone Derivatives Against Spodoptera frugiperda under Laboratory Conditions

Russian Journal of Bioorganic Chemistry, Journal Year: 2024, Volume and Issue: 50(3), P. 1037 - 1048

Published: June 1, 2024

Language: Английский

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Design, Synthesis, Antibacterial Activity, and Mechanisms of Novel Benzofuran Derivatives Containing Disulfide Moieties

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(18), P. 10195 - 10205

Published: April 25, 2024

The unsatisfactory effects of conventional bactericides and antimicrobial resistance have increased the challenges in managing plant diseases caused by bacterial pests. Here, we report successful design synthesis benzofuran derivatives using as core skeleton splicing disulfide moieties commonly seen natural substances with antibacterial properties. Most our developed benzofurans displayed remarkable activities to frequently encountered pathogens, including Xanthomonas oryzae pv (Xoo), oryzicola (Xoc), axonopodis citri (Xac). With assistance three-dimensional quantitative constitutive relationship (3D-QSAR) model, optimal compound V40 was obtained, which has better vitro activity EC50 values 0.28, 0.56, 10.43 μg/mL against Xoo, Xoc, Xac, respectively, than those positive control, TC (66.41, 78.49, 120.36 μg/mL) allicin (8.40, 28.22, 88.04 μg/mL). Combining results proteomic analysis enzyme assay allows mechanism be preliminarily revealed, suggesting its potential a versatile bactericide combating pests future.

Language: Английский

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Design, Synthesis, and Biological Evaluation of Asymmetrical Disulfides Based on Garlic Extract as Pseudomonas aeruginosa pqs Quorum Sensing Inhibitors

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

Pseudomonas aeruginosa is a widely encountered bacterium linked to the deterioration of food products and represents notable concern for public health safety. Disulfides serve as significant pharmacologically active scaffolds exhibiting antibacterial, antiviral, anticancer properties; however, reports on their activity quorum sensing inhibitors (QSIs) against P. are limited. In our work, asymmetrical disulfides were designed synthesized, utilizing natural products, such allicin, ajoene, diallyl disulfide (DADS), hordenine, cinnamic acid, lead compounds. By screening lasB, rhlA, pqsA promoter activity, two highly effective QSIs identified. Compounds 7d 4c show effectiveness in reducing synthesis different virulence factors, creation biofilms, movement capabilities. Subsequent validation using Galleria mellonella larvae model confirmed robust vivo efficacy. Moreover, combination with antibiotics markedly augmented antibacterial activity. Mechanism studies employed by transcriptome analysis, quantitative reverse transcription-PCR (qRT-PCR), surface plasmon resonance, molecular docking demonstrate that compound disrupts system interacting PqsR. These findings suggest derivatives hold promise treating infections.

Language: Английский

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Synthesis of α-ketothioamides with elemental sulfur under solvent-free conditions in a mixer mill

RSC Mechanochemistry, Journal Year: 2024, Volume and Issue: 1(1), P. 38 - 42

Published: Jan. 1, 2024

α-Ketothioamides are formed by a mechanochemical solvent-free Willgeroth–Kindler-type reaction starting from acetophenone derivatives, amines, and elemental sulfur.

Language: Английский

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Design, Synthesis, and Bioactivity of Trifluoroethylthio-Substituted Phenylpyrazole Derivatives

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(21), P. 11949 - 11957

Published: May 17, 2024

As the first marketed phenylpyrazole insecticide, fipronil exhibited remarkable broad-spectrum insecticidal activity. However, it poses a significant threat to aquatic organisms and bees due its high toxicity. Herein, 35 derivatives containing trifluoroethylthio group on 4 position of pyrazole ring were designed synthesized. The predicted physicochemical properties all compounds within reasonable range. biological assay results revealed that compound

Language: Английский

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Synthesis of N‐Monosubstituted Sulfondiimines by Metal‐free Iminations of Sulfilimium Salts

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(29)

Published: May 4, 2023

Sulfondiimines are marginalized entities among nitrogen-containing organosulfur compounds, despite offering promising properties for applications in various fields including medicinal and agrochemical. Herein, we present a metal-free rapid synthetic procedure the synthesis of N-monosubstituted sulfondiimines that overcomes current limitations their accessibility. Particularly, S,S-dialkyl substrates, which commonly difficult to convert by existing methods, react well with combination iodine, 1,8-diazabicyclo[5.4.0]undec-7-en (DBU), iminoiodinanes (PhINR) acetonitrile (MeCN) furnish corresponding yields up 85 % (25 examples). Valuable "free" NH-N'H-sulfondiimines can then be accessed N-deprotection under mild reaction conditions. Several experimental observations suggest mechanistic pathway diverging from common radical-based iodine/iminoiodinane mechanism. Based on results data obtained 1 H NMR spectroscopy, ESI mass spectrometry, crystallographic analysis propose direct amination PhINNs path via cationic iodonitrene.

Language: Английский

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Electrochemical cascade sequences for remote C7–H bond thiocyanation of quinoxalin-2(1H)-ones with ammonium thiocyanate

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(19), P. 7774 - 7781

Published: Jan. 1, 2023

Electrochemical cascade sequences for regioselective direct C7-thiocyanation of quinoxalin-2(1 H )-ones with ammonium thiocyanate have been developed.

Language: Английский

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A novel near-infrared fluorescence probe for selective sensing of cysteine over GSH and bioimaging in cells, zebrafish and plants

Microchemical Journal, Journal Year: 2023, Volume and Issue: 196, P. 109678 - 109678

Published: Nov. 19, 2023

Language: Английский

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Photoinduced Synthesis of Polycyclic γ‐Sultines by a Radical‐Polar Crossover Cyclization

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3478 - 3483

Published: Aug. 23, 2023

Abstract Described herein is a visible light‐mediated radical addition/SO 2 insertion/anionic cyclization of benzo‐fused homoallylic tosylates, allowing access to diverse array otherwise challenging‐to‐access fluoromethylated polycyclic γ ‐sultines with two adjacent tetrasubstituted carbon stereocenters in 49–95% yields, which can be further readily functionalized towards bulky carbon‐containing ‐sultone and mercaptoalkanol. Sodium fluoroalkanesulfinates were utilized as bifunctionalization reagents for both fluoromethyl groups SO . The proceeds through stepwise photoinduced addition followed by an intramolecular 5‐ exo‐tet anionic substitution after insertion.

Language: Английский

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