Synthesis, stability, and sulfur-elimination reactions of some bis(N-arylimidoyl) disulfides

Schaeffer, J.; Goodhue, C. T.; Risley, Hugh A.; Stevens, Richard E.

doi:10.1021/jo01288a029

Cited by 35 publications

(7 citation statements)

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“…Schaeffer and co‐workers2c synthesized disulfides by the reaction of N ‐arylthioamides with iodine in the presence of a base. Recently, Mali and Gopi2d reported the synthesis of disulfide from N ‐protected amino thioacids in the presence of I 2 in THF.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical and Photoelectrochemical Sensing of NADH and Ethanol Based on Immobilization of Electrogenerated Chlorpromazine Sulfoxide onto Graphene‐CdS Quantum Dot/Ionic Liquid Nanocomposite

2014

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Here, a simple one‐step solvothermal procedure was employed to synthesize a nanocomposite containing graphene‐nanosheets and CdS quantum dots (GNs‐CdS QDs). The electrochemical oxidation of chlorpromazine (CPZ) to chlorpromazine‐sulfoxide (CPZ‐SO) onto a GNs‐CdS QDs/ionic liquid (IL) nanocomposite modified glassy carbon (GC) electrode give rise to redox‐active products which showed excellent electrocatalytic and photoelectrocatalytic activity toward NADH oxidation at reduced overpotential. A linear response up to 200 µM was obtained for photoamperometric determination of NADH with detection limit 1 µM. Immobilizing alcohol dehydrogenase(ADH) onto the modified electrode via a simple cross linking procedure, the photoelectrochemical capability of the proposed system toward ethanol biosensing was clearly shown.

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Section: Resultsmentioning

confidence: 99%

Electrochemical and Photoelectrochemical Sensing of NADH and Ethanol Based on Immobilization of Electrogenerated Chlorpromazine Sulfoxide onto Graphene‐CdS Quantum Dot/Ionic Liquid Nanocomposite

2014

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“…The disulfide metabolites of phenylthiourea, propylthiouracil and thiobenzamide were prepared by oxidation of the parent drugs with iodine (11,12). Collagenase (from Clostridium histoliticum), 4-(2-hydroxyethyl)-l-piperazineethane sulfonic acid (Hepes) and bovine serum albumin were obtained from Boehringer-Mannheim (Montreal, Canada).…”

Section: Chemicalsmentioning

confidence: 99%

The Toxicity of Disulphides to Isolated Hepatocytes and Mitochondria

Jatoe

Lauriault²,

McGirr³

et al. 1988

Drug Metabolism and Drug Interactions

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CONTENTS Page SUMMARY " 396 I. IV. DISCUSSION ·. 406 V. ACKNOWLEDGEMENTS .410 VI. REFERENCES _ 411 Abbreviations used: RSSR = drug disulfide; Prot-SH = protein thiol; GSSR = glutathione-drug mixed disulfide; Prot-SSG = protein-drug mixed disulfide. 395 Brought to you by | University of Arizona Authenticated Download Date | 7/18/15 11:35 AM Vol. 6, No. 3/4, 1988 The Toxicity of Disulphides to Isolated Hepatocytes and Mitochondria SUMMARYThe disulfide metabolites of thiono-sulfur drugs were found to be about 50 to 100 times more toxic to isolated rat hepatocytes than the corresponding parent drugs. The order of decreasing cytotoxicity for the disulfide metabolites was disulfiram > propylthiouracil disulfide > formamidine disulfide > phenylthiourea disulfide > thiobenzamide disulfide > cystamine. Depletion of intracellular GSH levels preceded cytotoxicity. GSH could be restored and cytotoxicity averted by adding the thiol reducing dithiothreitol. Depletion of GSH with diethylmaleate potentiated the toxicity of disulfides 3 to 4-fold confirming the protective role of GSH in disulfide toxicity. The toxicity of disulfiram was increased 4-fold in cells pretreated with ATP (0.8mM) to effect a transient increase in cytosolic Ca 2 + suggesting an impairment of Ca 2 + homeostasis by the toxicant. Disulfiram (200μΜ) rapidly depleted hepatocyte ATP levels within 15 minutes which suggests that ATP production is inhibited. The disulfide effectiveness at causing mitochondrial Ca 2 + release was similar to their effectiveness at inducing hepatocyte cytotoxicity. These results suggest that hepatocyte toxicity is the result of oxidative inactivation of membrane protein thiols that regulate intracellular Ca 2 + homeostasis. 396Brought to you by |

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“…Sweetening of catalyst poisons thiols to low volatile disulfides in oil industries and also industrial applications of disulfides in vulcanization of rubbers and elastomers led us to investigate the introduction and applications of new member of this category of reagents in oxidation of thiols to the corresponding disulfides. This conversion has been accomplished using reagents such as molecular oxygen, [1] metal ions, [2] Bu3SnOMe/FeCl3, [3]nitric oxide, [4] halogens, [5][6][7] sodium perborate, [8]borohydride exchange resin (BER)-transition metal salt system, [9] a morpholine iodine complex, [10] pyridinium chlorochromate (PCC), [11] ammonium persulfate, [12] KMnO4 / CuSO4, [13] and Tributylammonium Halochromates [14]. There are some disadvantages in these reagents such as availability of the reagent, cumbersome procedure, high cost of the reagent, over oxidation or oxidation of other functional groups presented in thiols.…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted, Synthesis of Symmetrical Disulfides with Triethylammonium Halochromates, (C2H5)3NH+[CrO3X]-(X=F, Cl)

Mohammadi¹,

Ghammamy²,

Farjam³

2011

IJCEA

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Triethylammonium fluorochromate (TEAFC) and Triethylammonium chlorochromate (TEACC) are new efficient reagents, which are prepared easily and oxidized thiols to the corresponding disulfides swiftly. The reactions perform cleanly and terminate simultaneously at the disulfide stage without any side products. Oxidizing of some thiols to their corresponding disulfides was studied in solution at room temperature and under microwave radiation. The easy procedure, simple work-up, short reaction times, and excellent yields are advantages of these reagents.

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Synthesis, stability, and sulfur-elimination reactions of some bis(N-arylimidoyl) disulfides

Cited by 35 publications

References 0 publications

Electrochemical and Photoelectrochemical Sensing of NADH and Ethanol Based on Immobilization of Electrogenerated Chlorpromazine Sulfoxide onto Graphene‐CdS Quantum Dot/Ionic Liquid Nanocomposite

Electrochemical and Photoelectrochemical Sensing of NADH and Ethanol Based on Immobilization of Electrogenerated Chlorpromazine Sulfoxide onto Graphene‐CdS Quantum Dot/Ionic Liquid Nanocomposite

The Toxicity of Disulphides to Isolated Hepatocytes and Mitochondria

Microwave Assisted, Synthesis of Symmetrical Disulfides with Triethylammonium Halochromates, (C2H5)3NH+[CrO3X]-(X=F, Cl)

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