Rhenium-Catalyzed Oxidation of Thiols and Disulfides with Sulfoxides

Arterburn, Jeffrey B.; Perry, Marc C.; Nelson, Sherry L.; Dible, and Benjamin R.; Holguin, Mylena S.

doi:10.1021/ja972013r

Cited by 120 publications

(56 citation statements)

References 49 publications

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“…Nitro and sulfoxide compounds have many biological activities such as antiulcer, antibacterial, antifungal, anticancer, and antihypertensive activities [10][11][12][13][14][15][16][27][28][29]. However, antixanthine oxidase, antityrosinase, antielastase, and antineuraminidase activities of these compounds have not been investigated until now.…”

Section: Discussionmentioning

confidence: 99%

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Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

Onul

Ertik

Mermer

et al. 2018

Journal of Chemistry

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S-substituted perhalo-2-nitrobuta-1,3-dienes 3a, b were synthesized by the reaction of polyhalo-2-nitrobuta-1,3-dienes 1a, b with allyl mercaptan. 1-(2,3-Dibromopropanethio)-4-bromo-1,3,4-trichloro-2-nitrobuta-1,3-diene 4 was obtained from the addition of bromine to S-substituted polyhalo-2-nitrobuta-1,3-diene 3b in carbon tetrachloride. Sulfoxides 5a, b, and 6 were obtained from the reaction of thiosubstituted polyhalonitrobutadienes 3a, b, and 4 with m-CPBA in CHCl 3 . The structures of the new compounds were determined by spectroscopic data (FTIR, 1 H NMR, 13 C NMR, MS). These compounds exhibited antixanthine oxidase, antityrosinase, antielastase, and antineuraminidase activities.

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Section: Discussionmentioning

confidence: 99%

“…In the literature, these compounds have been termed as "chemical chameleons." They are used as synthetic mediators in the syntheses of several organic compounds having antiulcer, antibacterial, antifungal, and antihypertensive properties [27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

Onul

Ertik

Mermer

et al. 2018

Journal of Chemistry

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“…DMSO by itself [59][60][61] or in combination with various acidic co-reagents [62][63][64] mediates the transformation of thiols to disulfides. The palladium catalyst may also be involved in this oxidation step, because the heating of 17a in DMSO at 120°C in the absence of palladium resulted in the formation of disulfide 19a in only 11% yield.…”

Section: -46)mentioning

confidence: 99%

“…The palladium catalyst may also be involved in this oxidation step, because the heating of 17a in DMSO at 120°C in the absence of palladium resulted in the formation of disulfide 19a in only 11% yield. 62,63,[65][66][67] Disulfide 19 formed from the corresponding ethenethiol 17 may undergo oxidative addition to palladium, leading to complex 20. 68,69) Subsequent C-H cyclization can give rise to the desired benzo[b] thiophene 18.…”

Section: -46)mentioning

confidence: 99%

Synthesis of Heterocyclic Compounds through Palladium-Catalyzed C–H Cyclization Processes

Inamoto

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon-hydrogen bond (C-H) functionalization/intramolecular carbon-heteroatom (nitrogen or sulfur) bond formation process. By this C-H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C-H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.

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“…[1][2][3][4][5][6] They playacrucial role in maintaining the conformationals tability and biological activity of proteins [1,2] and participate in the adhesion process of mussel foot protein. [4,5] Over the past decades, these chemicals have received much attentiona saresult of their artificial applicationsi ns ynthesizing pharmaceutical molecules, [7,8] constructing functional materials, [9][10][11] building dynamic combinatorial libraries, [12,13] and preparing sulfur-containing organic compounds.…”

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confidence: 99%

Polydopamine as a Catalyst for Thiol Coupling

Yang

et al. 2015

ChemCatChem

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In biological systems, disulfide bonds are formed efficiently under mild conditions without the release of harmful byproducts. Inspired by nature, we report a biomimetic polydopamine (PDA) catalyst for oxidative thiol coupling. This reaction was accelerated with only a small amount of PDA particles in neutral, weakly alkaline, and even weakly acidic aqueous media at room temperature under an air atmosphere. The catalytic particles were facilely separated and were reused without a decrease in activity. The entire process is totally biofriendly, including the synthesis of the PDA particles. This route is especially useful for the synthesis of pharmaceutical molecules.

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Rhenium-Catalyzed Oxidation of Thiols and Disulfides with Sulfoxides

Cited by 120 publications

References 49 publications

Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

Synthesis of Heterocyclic Compounds through Palladium-Catalyzed C–H Cyclization Processes

Polydopamine as a Catalyst for Thiol Coupling

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