- Targeted Delivery of Persulfides to the Gut: Effects on the Microbiome
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Persulfides (R?SSH) have been hypothesized as potent redox modulators and signaling compounds. Reported herein is the synthesis, characterization, and in vivo evaluation of a persulfide donor that releases N-acetyl cysteine persulfide (NAC-SSH) in response to the prokaryote-specific enzyme nitroreductase. The donor, termed NDP-NAC, decomposed in response to E. coli nitroreductase, resulting in release of NAC-SSH. NDP-NAC elicited gastroprotective effects in mice that were not observed in animals treated with control compounds incapable of persulfide release or in animals treated with Na2S. NDP-NAC induced these effects by the upregulation of beneficial small- and medium-chain fatty acids and through increasing growth of Turicibacter sanguinis, a beneficial gut bacterium. It also decreased the populations of Synergistales bacteria, opportunistic pathogens implicated in gastrointestinal infections. This study reveals the possibility of maintaining gut health or treating microbiome-related diseases by the targeted delivery of reactive sulfur species.
- Dillon, Kearsley M.,Morrison, Holly A.,Powell, Chadwick R.,Carrazzone, Ryan J.,Ringel-Scaia, Veronica M.,Winckler, Ethan W.,Council-Troche, R. McAlister,Allen, Irving C.,Matson, John B.
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supporting information
p. 6061 - 6067
(2021/02/01)
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- A novel dual-nano assisted synthesis of symmetrical disulfides from aryl/alkyl halides
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Here, we have reported a novel approach towards dual-nano assisted synthesis of disulfides from coupling of alkyl/aryl halides and sulfur nanoparticles. The indium oxide nanoparticles as catalyst expedite the conversion and sulfur nanoparticle notably enhances the miscibility, providing a faster, high yielding and cost-effective process in ethanol-water system. The method has synthetic advantages in terms of mild reaction framework, catalyst regeneration, and absence of any sulfide or polysulfide linkage as by-product leading to a column free synthesis. A variety of alkyl, aryl and heteroaryl symmetrical disulfides are obtained in good to excellent yields up to exceeding 98%.
- Devi, Namita,Hazarika, Sukanya,Gogoi, Prasanta,Barman, Pranjit
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supporting information
p. 1927 - 1938
(2018/07/21)
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- Symmetrical disulfide synthesis via nickel-catalysis using potassium sulfide as sulfur source
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Abstract: An efficient one-pot method for the synthesis of organic disulfides from aryl and alkyl halides and potassium sulfide has been described. K2S acts as an inexpensive and readily available sulfur source. A variety of symmetric diaryl and dialkyl disulfides was prepared in good to excellent yields using NiCl2·6H2O and acetylacetone as the catalytic system. Graphical abstract: [Figure not available: see fulltext.]
- Soleiman-Beigi, Mohammad,Arzehgar, Zeinab
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p. 1759 - 1763
(2016/09/28)
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- An efficient one-pot method for the direct synthesis of organic disulfides from aryl/alkyl halides in the presence of CuCl using morpholin-4-ium morpholine-4-carbo-dithioate
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A novel and expedient route is described for the one-pot synthesis of symmetric diaryl (dialkyl) disulfides derivatives via morpholin-4-ium morpholine-4-carbo-dithioate and aryl (alkyl) halides reactions in the presence of CuCl in an aqueous solvent system. Morpholin-4-ium morpholine-4-carbo-dithioate used as new solid, stable and easy handle sulfur Sourcage.
- Soleiman-Beigi, Mohammad,Arzehgar, Zeinab
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p. 395 - 402
(2015/06/22)
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- A novel nickel-catalyzed domino method for the direct synthesis of symmetrical disulfides using potassium 5-methyl-1,3,4-oxadiazole-2-thiolate as a sulfurating reagent
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A simple, one pot, efficient, and novel protocol has been developed for the direct synthesis of symmetrical organic disulfides using a domino reaction between an aryl/alkyl halide and potassium 5-methyl-1,3,4-oxadiazole-2-thiolate in the presence of NiCl2 as catalyst. A variety of symmetrical aryl/alkyl disulfides can be obtained in moderate to excellent yields (up to 95%).
- Soleiman-Beigi, Mohammad,Mohammadi, Fariba
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supporting information
p. 911 - 914
(2015/04/27)
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- Ni-Catalyzed Cross-Coupling Reaction: The Direct Synthesis of Symmetrical Disulfanes from Aryl and Primary Alkyl Halides
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A novel Ni-catalyzed cross-coupling reaction is introduced for the direct synthesis of diaryldisulfanes and dialkyldisulfanes from aryl halides and primary alkyl halides at normal atmospheric conditions, respectively. This one-pot and domino protocol utilizes only 10 mol% of NiCl2 as a catalyst and morpholin-4-ium morpholine-4-carbo-dithioate as a new, stable, solid, and odorless sulfurating reagent in the presence of ethylene glycol as a cosolvent and bidentate ligand in dimethyl formamide (DMF) at 130°C with good to excellent yields and relatively short time reaction.
- Soleiman-Beigi, Mohammad,Arzehgar, Zeinab
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p. 355 - 360
(2015/09/22)
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- An efficient, one-pot and CuCl-catalyzed route to the synthesis of symmetric organic disulfides via domino reactions of thioacetamide and aryl (alkyl) halides
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In this article, a simple, general and novel method for the synthesis of diaryl (dialkyl) disulfides from aryl (alkyl) halides is described. This is a convenient approach that involves the use of commercially available and inexpensive thioacetamide as a sulfur transfer reagent in the domino process for the synthesis of symmetric organic disulfides. Copyright
- Soleiman-Beigi, Mohammad,Hemmati, Maryam
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p. 734 - 736
(2013/12/04)
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- B12 Mimicry in a Weak Ligand Environment: Oxidation and Alkylation of Thiols
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The first examples of alkylation and oxidation of thiols by cobalt in weakly coordinating ligand (MeCN) environments is presented as a mimic to B12-dependent nonenzymatic reaction.
- Chowdhury, Shantanu,Samuel, Purnima M.,Das, Indira,Roy, Sujit
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p. 1993 - 1994
(2007/10/02)
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- Attempts to Synthesize Sterically Hindered Thiazyl Arenes and Their Relationship to Arylsulfenyl Nitrenes
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Up till now all attempts to synthesize organic thiazyl compounds in substance failed.Stabilization leads to the corresponding disulfide 2, the thioaminyl radical 7 and the sulphur diimide 8.Formally thiazyl compounds 1 and sulfenyl nitrenes 1 were resonance structures.Via sulfenyl nitrenes 1 the formation of 2, 7, 8 can be discussed.An in situ preparation of sulfenyl nitrene 1a via the sulfenyl chloride 5a, synthesized by chlorination of the disulfide 2a, and the sulfenyl azide 6a is described in detail. 1a can also be prepared from the sulfenyl amide 4a by oxidation.The structures of the radicals 7a-f and 12f are discussed.
- Mayer, R.,Decker, D.,Bleisch, S.,Domschke, G.
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- IMINATION OF SULFUR-CONTAINING COMPOUNDS. XXV. ARYLSULFONYLIMINATION OF BIS(ARYLSULFENYL)AMINES
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The imination of bis(arylsulfenyl)amines with N-sodio-N-chlorosulfonamides takes place anomalously with the formation of N,N'-bis(arylsulfonyl)arenesulfinamidines and N-(arylsulfonyl)arenesulfinamidines.This is due to the instability of the sulfur-nitroge
- Koval', I. V.,Tarasenko, A. I.,Kremlev, M. M.,Naumenko, R. P.
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p. 1060 - 1064
(2007/10/02)
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- INVESTIGATION IN THE REGION OF THIOSULFONIC ACIDS. XXXII. REACTION OF ARYL ESTERS OF THIOSULFONIC ACIDS WITH SUBSTANCES CONTAINING AN ACTIVE METHYLENE GROUP
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The reactions of the aryl esters of thisulfonic acids with diethyl malonate, ethyl acetoacetate, ethyl cyanoacetate, and acetylacetone in the presence of sodium alcoholates were investigated at various temperatures.Without heat the reaction takes place with the formation of sulfinates and arenesufenic esters, which form their thio derivatives when heated with substances containing an active methylene group in the presence of sodium alcoholates.It was thus demonstrated that under the investigated conditions thioarylating characteristics are exhibited not by the aryl esters of the thiosulfonic acids but by the esters of arenesufenic acids formed as the initial products of these reactions.
- Boldyrev, B. G.,Aristarkhova, L. N.,Stoyanovskaya, Ya. I.,Bilozor, T. K.
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p. 1160 - 1167
(2007/10/02)
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- Nucleophilic Aromatic Substitution promoted by Lipophilic Quaternary Onium Salts under Phase-transfer Conditions and in Low Polarity Anhydrous Solvents. A Kinetic Study
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A kinetic study of aromatic nucleophilic substitutions by N3(1-) and SCN(1-) has been carried out under phase-transfer catalysis (p.t.c.) conditions and in anhydrous chlorobenzene in the presence of hexadecyltributylphosphonium azide and thiocyanate.Under p.t.c. conditions, reactions follow a pseudo-first-order kinetic equation, and kobs is linearly related to the nucleophile concentration in the organic phase.In most reactions, the rate-determining step is attack by the nucleophile on the substrate.However in a few cases the process is controlled by diffusion ofthe anions through the interface.Passing from p.t.c. conditions to chlorobenzene solution leads to 5-7- and 2-3-fold increases in reaction rates with N3(1-) and SCN(1-), respectively.This behaviour is analogous to that observed in the aliphatic series, and is probably due to the limited number of water molecules accompanying the anions in the organic phase under p.t.c. conditions.Nucleofugicity scales are related to the polarizability of the nucleophile, and with N3(1-) and SCN(1-) they are F>>Br>=I>=Cl and Br>I>F>=Cl, respectively.Reaction products, including those derived from successive decomposition of N3 and SCN groups, have been identified.
- Landini, Dario,Maia, Angelamaria,Montanari, Fernando
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p. 461 - 466
(2007/10/02)
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- In Search of New Sulfur Transfer Agents
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The chemistry of various sulfur-transfer agents is studied.The reaction of aromatic sulfenyl chloride 5 in the presence of imidazole and/or triethylamine gives the aryl disulfides 7 in 14-85 percent yield, whereas in the case of the corresponding benzylsulfenyl chlorides 9 in the presence of triethylamine and/or caprolactam, both disulfide 10 and benzyl chlorides 11 are formed in 0-81 precent and 10-72 precent yield, respectively. - The transfer reactions of 3-sulfenylated hydantoins 18 with amines are useful for the preparation of the unsymmetric sulfenamides 20 in 31 -61 percent yield.Analogous transfer reactions of compounds 23 and 24 with piperidine give N,N'-thiodipiperidine (3, X = CH2) in 71-80 percent.
- Sosnovsky, George,Krogh, James A.
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p. 121 - 136
(2007/10/02)
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