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Sulfenamide formation - chemical and biochemical reactions and their applications in cell biology

JOURNAL OF SULFUR CHEMISTRY (2023)

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Article Chemistry, Organic

One-Pot Tandem Oxidative Bromination and Amination of Sulfenamide for the Synthesis of Sulfinamidines

Gao-feng Yang et al.

Summary: In this study, a tandem oxidative/nucleophilic substitution approach for the synthesis of sulfinamidines was developed. The reaction, enabled by N-bromosuccinimide (NBS) as an oxidant and various readily available amines as nucleophiles, achieved high yields (up to 98%) without the need for any additives or catalysts. This method offers the advantages of being time-efficient, safe, easy to scale up, and compatible with diverse functional groups.

JOURNAL OF ORGANIC CHEMISTRY (2023)

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Review Pharmacology & Pharmacy

Metformin derivatives - Researchers' friends or foes?

Sema Tuna Torunoglu et al.

Summary: Metformin has been widely used to treat diabetes mellitus due to its safety profile and low cost. However, its pharmacokinetics vary among patients, and its poor oral absorption leads to high therapeutic doses and unpleasant gastrointestinal side effects. Novel derivatives of metformin have been synthesized, especially after the identification of organic cation transporters as its main carriers. These derivatives have shown potential in the treatment of various diseases, including cancers and neurodegenerative diseases.

BIOCHEMICAL PHARMACOLOGY (2023)

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Article Chemistry, Physical

Synthesis and characterization of novel sulfonamide functionalized maleimide polymers: Conventional kinetic analysis, antimicrobial activity and dielectric properties

Ibrahim Erol

Summary: Novel maleimide monomers were synthesized and characterized in this study. The structural properties, thermal stability, and biological activities of the resulting polymers were investigated. Furthermore, the molecular weights, photochemical properties, physical constants, and dielectric properties of the polymers were determined.

JOURNAL OF MOLECULAR STRUCTURE (2022)

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Article Chemistry, Multidisciplinary

Multistep Continuous Flow Synthesis of Isolable NH2-Sulfinamidines via Nucleophilic Addition to Transient Sulfurdiimide

Michael Andresini et al.

Summary: This study reports a multistep continuous flow synthesis method for the preparation of poorly explored NH2-sulfinamidines by nucleophilic attack of organometallic reagents. The method allows for the synthesis of the target compounds under mild conditions via a highly chemoselective halogen-lithium exchange reaction, and the synthetic potential of the methodology was evaluated.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

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Article Chemistry, Organic

Sulfinimidate Esters as an Electrophilic Sulfinimidoyl Motif Source: Synthesis of N-Protected Sulfilimines from Grignard Reagents

Michael Andresini et al.

Summary: The reactivity of sulfinimidate esters as electrophilic sulfinimidoyl motif source and their reaction with Grignard reagents for preparation of protected sulfilimines were investigated for the first time in this work. Results showed high yields, remarkable structural variability, and environmentally responsible conditions using CPME as a green solvent for this transformation.

ORGANIC LETTERS (2021)

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Review Chemistry, Multidisciplinary

Direct synthesis of sulfenamides, sulfinamides, and sulfonamides from thiols and amines

Yan Cao et al.

Summary: Organosulfur compounds with sulfur-nitrogen bonds have diverse applications in fields such as pharmaceuticals, agrochemicals, and polymers. Recent advances in the oxidative coupling of thiols and amines have allowed for the efficient synthesis of sulfenamides, sulfinamides, and sulfonamides in a single step, streamlining synthetic routes and reducing waste generation. This attractive research area focuses on developing environmentally friendly and economic processes for the preparation of important compounds in the pharmaceutical industry.

RSC ADVANCES (2021)

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Review Biophysics

Sulfonamide drugs: structure, antibacterial property, toxicity, and biophysical interactions

Aben Ovung et al.

Summary: Sulfonamide drugs have various pharmacological activities and can be used to treat a variety of diseases, such as sulfamethazine for bacterial infections in veterinary medicine and sulfadiazine for treating toxoplasmosis in livestock.

BIOPHYSICAL REVIEWS (2021)

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Article Chemistry, Medicinal

An amide-based sulfenamide prodrug of gamma secretase inhibitor BMS-708163 delivers parent drug from an oral conventional solid dosage form in male beagle dog

Victor R. Guarino et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2020)

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Review Chemistry, Multidisciplinary

Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds

Elzbieta Wojaczynska et al.

CHEMICAL REVIEWS (2020)

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Article Chemistry, Organic

Synthesis of Sulfinamidines and Sulfinimidate Esters by Transfer of Nitrogen to Sulfenamides

Michael Andresini et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Medicinal

Sulfonamide derivatives as multi-target agents for complex diseases

Sinem Apaydin et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2019)

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Article Biochemistry & Molecular Biology

Sulfenamide and sulfonamide derivatives of metformin can exert anticoagulant and profibrinolytic properties

Magdalena Markowicz-Piasecka et al.

CHEMICO-BIOLOGICAL INTERACTIONS (2018)

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Review Chemistry, Applied

Sulfonimidamides: Synthesis and Applications in Preparative Organic Chemistry

Ganesh Chandra Nandi et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

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Article Cell Biology

Metformin and Its Sulfenamide Prodrugs Inhibit Human Cholinesterase Activity

Magdalena Markowicz-Piasecka et al.

OXIDATIVE MEDICINE AND CELLULAR LONGEVITY (2017)

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Article Chemistry, Organic

Unsymmetrical disulfide and sulfenamide synthesis via reactions of thiosulfonates with thiols or amines

Nobukazu Taniguchi

TETRAHEDRON (2017)

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Article Chemistry, Physical

Revealing the Mechanistic Pathway of Acid Activation of Proton Pump Inhibitors To Inhibit the Gastric Proton Pump: A DFT Study

Kalyanashis Jana et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2016)

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Review Cell Biology

DNA Damage Response and Metabolic Disease

Ippei Shimizu et al.

CELL METABOLISM (2014)

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Article Chemistry, Medicinal

Sustained Release of Metformin via Red Blood Cell Accumulated Sulfenamide Prodrug

Lauri Peura et al.

JOURNAL OF PHARMACEUTICAL SCIENCES (2014)

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Article Pharmacology & Pharmacy

Convenient microwave-assisted synthesis of lipophilic sulfenamide prodrugs of metformin

Kristiina M. Huttunen et al.

EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES (2013)

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Article Chemistry, Medicinal

Determination of the permeability characteristics of two sulfenamide prodrugs of linezolid across Caco-2 cells

Kwame W. Nti-Addae et al.

JOURNAL OF PHARMACEUTICAL SCIENCES (2012)

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Article Chemistry, Organic

FAST AND EFFICIENT SYNTHESIS OF SULFINAMIDES BY THE OXIDATION OF SULFENAMIDES USING POTASSIUM FLUORIDE AND m-CHLOROPEROXYBENZOIC ACID

Mrityunjoy Datta et al.

SYNTHETIC COMMUNICATIONS (2012)

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Article Chemistry, Medicinal

In Vitro Conversion of Model Sulfenamide Prodrugs in the Presence of Small Molecule Thiols

Kwame W. Nti-Addae et al.

JOURNAL OF PHARMACEUTICAL SCIENCES (2011)

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Article Chemistry, Organic

Copper-Catalyzed Formation of Sulfur-Nitrogen Bonds by Dehydrocoupling of Thiols with Amines

Nobukazu Taniguchi

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2010)

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Article Medicine, Research & Experimental

Butyrylcholinesterase in metabolic syndrome

Gumpeny R. Sridhar et al.

MEDICAL HYPOTHESES (2010)

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Article Chemistry, Medicinal

Discovery and Evaluation of BMS-708163, a Potent, Selective and Orally Bioavailable γ-Secretase Inhibitor

Kevin W. Gillman et al.

ACS MEDICINAL CHEMISTRY LETTERS (2010)

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Article Chemistry, Medicinal

The First Bioreversible Prodrug of Metformin with Improved Lipophilicity and Enhanced Intestinal Absorption

Kristiina M. Huttunen et al.

JOURNAL OF MEDICINAL CHEMISTRY (2009)

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Article Agriculture, Multidisciplinary

ELISA for sulfonamides and its application for screening in water contamination

Weilin L. Shelver et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2008)

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Article Peripheral Vascular Disease

Attenuation of hypertension development by scavenging methylglyoxal in fructose-treated rats

Xiaoxia Wang et al.

JOURNAL OF HYPERTENSION (2008)

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Article Chemistry, Medicinal

Preparation, characterization and in vivo conversion of new water-soluble sulfenamide prodrugs of carbamazepine

Rey N. Hemenway et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2007)

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Article Chemistry, Organic

Copper-catalyzed synthesis of sulfenamides utilizing diaryl disulfides with alkyl amines

Nobukazu Taniguchi

SYNLETT (2007)

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Article Biochemistry & Molecular Biology

N-thiolated β-lactams:: Studies on the mode of action and identification of a primary cellular target in Staphylococcus aureus

Kevin D. Revell et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2007)

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Article Chemistry, Medicinal

Sulfenamides as prodrugs of NH-acidic compounds: A new prodrug option for the amide bond

Victor R. Guarino et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2007)

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Article Multidisciplinary Sciences

Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer β-amyloid peptide in rodent

NH Greig et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2005)

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Article Polymer Science

The action of N-(cyclohexylthio)phthalimide as a prevulcanization inhibitor of 2-bisbenzothiazole-2,2′-disulfide accelerated sulfur vulcanization

MHS Gradwell et al.

RUBBER CHEMISTRY AND TECHNOLOGY (2001)

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