Divergent Generation of the Difluoroalkyl Radical and Difluorocarbene via Selective Cleavage of C–S Bonds of the Sulfox-CF₂SO₂Ph Reagent

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 872 - 876

Published: Jan. 18, 2024

A new difluoroalkylation reagent Sulfox-CF2SO2Ph bearing both sulfoximine and sulfone moieties was prepared from commercially available SulfoxFluor PhSO2CF2H. On one hand, the could act as a (phenylsulfonyl)difluoromethyl radical source under photoredox catalysis, in which arylsulfoximidoyl group is selectively removed. other basic conditions, serve difluorocarbene precursor for S- O-difluoromethylations with O-nucleophiles, respectively, phenylsulfonyl removed (followed by α-elimination of group).

Language: Английский

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Caffeine and Nicotine with N-Substituted Diazirine Photoaffinity Labels Form Adducts at Tyrosine-39 of α-Synuclein

ACS Chemical Neuroscience, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Aggregates of the protein α-synuclein are found in Lewy bodies brains Parkinson's disease (PD) patients. Small molecules that can attenuate or halt aggregation have been studied as potential therapeutics for PD. However, we a limited understanding how these bind to α-synuclein. We previously identified caffeine, nicotine, and 1-aminoindan all both N- C-terminus α-synuclein, although binding location remains unknown. In an effort identify regions on synthesized diazirine photoaffinity probes attached caffeine (C-Dz), nicotine (N-Dz), (I-Dz) allowed each react with vitro. then treated incubation mixture trypsin employed time-of-flight mass spectrometry analyze resulting peptides. Our findings reveal distinctive pattern among probes: C-Dz forms covalent bonds Tyr-39 Glu-20, while N-Dz selectively bond Tyr-39. Intriguingly, could not detect labeling I-Dz any specific amino acids. All diazirine-bound peptides were near N-terminus. results suggest N-terminal region bears further study elucidate interactions small may be target anti-PD agents.

Language: Английский

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In vitro activity of novel 4-iminohydantoin sulfamide derivatives against human cytomegalovirus

Chemical Papers, Journal Year: 2023, Volume and Issue: 78(1), P. 133 - 140

Published: Sept. 15, 2023

Language: Английский

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In Silico, in Vitro and in Vivo Study of Substituted Imidazolidinone Sulfonamides as Antibacterial Agents

Chemistry & Biodiversity, Journal Year: 2023, Volume and Issue: 20(12)

Published: Nov. 9, 2023

Abstract New substituted imidazolidinone sulfonamides have been developed using a rational drug design strategy. Predictive QSAR models for the search of new antibacterials were created OCHEM platform. Regression applied to verify virtual chemical library derivatives designed antibacterial activity. A number as effective agents identified by prediction, synthesized and characterized spectral elemental, tested in vitro . Six studied compounds shown highest activity against Gram‐negative E. coli Gram‐positive S. aureus multidrug‐resistant strains. The vivo acute toxicity these based on LC 50 value ranged from 16.01 44.35 mg/L (slightly toxic class). results molecular docking suggest that mechanism can be associated with inhibition post‐translational modification processes bacterial peptides proteins.

Language: Английский

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Development of Diazirine–Alkyne Tag for Protein–Ligand Interaction Analysis with Photoaffinity Labeling

Published: Jan. 1, 2024

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Language: Английский

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Development of diazirine–alkyne tag for protein–ligand interaction analysis with photoaffinity labeling

Chemistry Letters, Journal Year: 2024, Volume and Issue: 53(8)

Published: July 31, 2024

Abstract We have developed a diazirine–alkyne tag for target protein–ligand interaction analysis. A sulfonamide photoaffinity probe was readily prepared using copper-catalyzed azide–alkyne cycloaddition (CuAAC), which site-specifically formed covalent bond with human carbonic anhydrase 1 (∼30% labeling yield). The photolabeled position (E58–H64 region) determined based on the results of tandem mass spectrometry (MS/MS) analysis tryptic peptides and supported by molecular modeling studies. Our method may be useful determining unknown ligand-binding sites various biomolecules.

Language: Английский

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Synthesis of Aryl Fluorocyclopropanes from Aryl Fluorodiazirines and Alkenes in Continuous Flow

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Photochemically induced generation of aryl fluorocarbenes from fluorodiazirines and their subsequent [2+1] cycloaddition with alkenes was developed in continuous flow. The

Language: Английский

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In silico modeling and experimental validation of 2-oxoimidazolidin-4-sulfonamides as low-toxicity fungicides against Phytophthora infestans

Advanced Agrochem, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Language: Английский

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