A Facile Synthesis of 3<i>H</i>-Benzo[1,2]Dithiole-3-Thiones and Their Condensation with Active Methylene Compounds

Jin, Hongwei; Dong, Jing; Gao, Jianrong; Gen-rong, Qiang; Gong, Yuan

doi:10.1080/10426507.2011.600743

Cited by 8 publications

(10 citation statements)

References 16 publications

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“…Three methods were utilized in the synthesis of 59 target dithiolethiones in this work, namely, compound 1 by the method of Behringer et al, compound 6 by method of Jin et al, and the other compounds by the method of Curphey . All target compounds were characterized through 1 H NMR, 13 C NMR, and MS analyses.…”

Section: Results and Discussionmentioning

confidence: 99%

“…Target Compounds Synthesis and Characterization. Compound 1 and compound 6 were synthesized by the methods invented by Behringer et al 55 and Jin et al 56 without any modification, respectively. Except for compounds 1 and 6, the other target compounds were synthesized in the light of the procedure developed by Curphey 57 with a little optimization.…”

Section: Methodsmentioning

confidence: 99%

“…[1,2]dithiole-3-thione (Compound 6). Compound 6 was prepared from d1 as starting material following the method developed by Jin et al 56 to provide an orange solid. Yield: 74.5%.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Song

Bai

Zhang

et al. 2020

J. Agric. Food Chem.

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Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes’ products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Song

Bai

Zhang

et al. 2020

J. Agric. Food Chem.

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“…tween para-methylbenzaldehyde and para-methoxyaniline (Table 2, Entry 16). [11] Although a detailed mechanistic investigation of this process awaits additional experimentation, two possible routes to form the thioamides might exist, as shown in Scheme 1. However, ortho-chlorobenzaldehyde delivered 3H-1,2benzodithiole-3-thione as the major product without the formation of the desired thioamide product.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Thioamides by Catalyst‐Free Three‐Component Reactions in Water

Deng

et al. 2013

Eur J Org Chem

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“…The suggested mechanism for this [3+2] cycloaddition includes attack of elemental sulfur on the positively charged carbon atom of the cyclopropenthione derivative followed by release of S 6 with a further ring-opening/cyclization sequence to give dithiolethiones. Substituted 3H-benzo [1,2]dithiole-3-thiones 33 can be prepared by treatment of 2bromobenzaldehydes with potassium sulfide in DMF [73]. This method is superior to those previously described for benzodithiolethiones in terms of the number of steps and efficiency (Scheme 31).…”

Section: Miscellaneous Syntheses Of 3h-12-dithiole-3-thionesmentioning

confidence: 96%

Synthesis and Reactivity of 3H-1,2-dithiole-3-thiones

Ракитин

2021

Molecules

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3H-1,2-Dithiole-3-thiones are among the best studied classes of polysulfur-containing heterocycles due to the almost explosive recent interest in these compounds as sources of hydrogen sulfide as an endogenously produced gaseous signaling molecule. This review covers the recent developments in the synthesis of these heterocycles, including both well-known procedures and important novel transformations for building the 1,2-dithiole-3-thione ring. Diverse ring transformations of 3H-1,2-dithiole-3-thiones into various heterocyclic systems through 1,3-dipolar cycloaddition, replacement of one or two sulfur atoms to form carbon- and carbon-nitrogen containing moieties, and other unexpected reactions are considered.

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A Facile Synthesis of 3H-Benzo[1,2]Dithiole-3-Thiones and Their Condensation with Active Methylene Compounds

Cited by 8 publications

References 16 publications

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Synthesis of Thioamides by Catalyst‐Free Three‐Component Reactions in Water

Synthesis and Reactivity of 3H-1,2-dithiole-3-thiones

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