6921-83-1Relevant articles and documents
Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes
Bai, Feifei,Fang, Jianguo,Song, Zi-Long,Zhang, Baoxin
, p. 2214 - 2231 (2020/03/06)
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.
1,2-dithio-3-thioketone derivative synthesized by cyclizing of fluorine-sulfur removal of trifluoropropyne via copper catalyzing
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Paragraph 0026, (2018/11/03)
The invention discloses a 1,2-dithio-3-thioketone derivative synthesized by cyclizing of fluorine-sulfur removal of trifluoropropyne via copper catalyzing. The 1,2-dithio-3-thioketone derivative is prepared by the following steps of using a 2-chloro-3,3,3-trifluoro-1 propene compound as a primer; adding cuprous bromide as a catalyst into the primer, using cesium carbonate as alkaline, using tetramethylethylenediamine as a ligand, using elemental sulfur as a sulfur source, and stirring to react for 12 hours in a N,N-dimethyl formamide solvent at the temperature of 120 DEG C; after reaction is finished, filtering a reaction liquid, extracting a filtrate twice by a saturated sodium chloride solution, reversely extracting once, separating to obtain an organic phase, and drying with anhydrous sodium sulfate; filtering again, and removing the solvent out of the filtrate by a rotary evaporator, so as to obtain the remaining matter; performing column chromatography separating on the remainingmatter by a silicon gel column, spraying by an elution solution, and collecting an effluent solution containing the target product; combining the effluent solution, concentrating under the vacuum condition, and removing the solvent, so as to obtain the target product. The 1,2-dithio-3-thioketone derivative has the advantages that the raw materials are simple and are easy to obtain, the preparationtechnology is novel and simple, the pollution is little, the energy consumption is low, and the yield rate is high.
Switching Selectivity of α-Enolic Dithioesters: One Pot Access to Functionalized 1,2- and 1,3-Dithioles
Koley, Suvajit,Chanda, Tanmoy,Samai, Subhasis,Singh, Maya Shankar
, p. 11594 - 11602 (2016/12/09)
An operationally simple cascade protocol has been developed for the construction of 1,2- and 1,3-dithiole derivatives from α-enolic dithioesters. 1,2-Dithioles are achieved by the reaction of dithioesters with elemental sulfur in the presence of InCl3 under solvent-free conditions. 1,3-Dithioles have been constructed via DABCO mediated self-coupling of dithioesters in open air enabling the formation of two new C-S bonds and one ring in a single operation in contiguous fashion. The reactions proceeded smoothly affording the desired sulfur-rich heterocycles in good to excellent yields, exhibiting gram-scale ability and broad functional group tolerance utilizing easy to handle cheap and easily available reagents. The probable mechanisms for the formation of 1,2- and 1,3-dithioles from α-enolic dithioesters have been suggested.
