3445-76-9

Usage

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 7231, 1993 DOI: 10.1016/S0040-4039(00)79295-1

InChI:InChI=1/C9H6S3/c10-9-6-8(11-12-9)7-4-2-1-3-5-7/h1-6H

Upstream product

• 300-57-2 allylbenzene 
• 1006-67-3 5-phenylisoxazole 
• 7713-79-3 3-phenyl-5-isoxazolone 
• 827-42-9 5-phenyl-3H-1,2-dithiol-3-one 
• 5653-30-5 2-[1,3]dithiolan-2-ylidene-1-phenyl-ethanone 
• 873-66-5 1-propenylbenzene 
• 15185-51-0 3-oxo-3-phenyl-dithiopropionic acid 
• 13636-88-9 3,3-bis(methylthio)-1-phenylprop-2-en-1-one 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 4192-77-2 ethyl cinnamate 
• 1779-81-3 4,5-Dihydro-thiazol-2-ylamin 
• 96-50-4 2-thiazolylamine 

Downstream Products

• 827-42-9 5-phenyl-3H-1,2-dithiol-3-one 
• 4849-59-6 5-phenyl-3-methylthio-1,2-dithiolium iodide 
• 15058-83-0 5-phenyl-[1,2]dithiol-3-one oxime 
• 152547-93-8 2-(2-Oxo-2-phenyl-ethylidene)-[1,3]dithiole-4,5-dicarbaldehyde 
• 152547-68-7 5-Diethoxymethyl-2-[2-oxo-2-phenyl-eth-(Z)-ylidene]-[1,3]dithiole-4-carbaldehyde 
• 1457-24-5 3,5-diphenyl-2,4-thiophenedicarboxylic acid 
• 87694-19-7 methyl 3,5-diphenyl-4-methoxycarbonyl-2-thiophenecarboxylic acid 
• 1974-94-3 dimethyl 3,5-diphenylthiophene-2,4-dicarboxylate 
• 828-78-4 4-bromo-5-phenyl-3H-1,2-dithiol-3-one 
• 857-54-5 dimethyl 3,6-diphenyl-1,4-dithiin-2,5-dicarboxylate 

Relevant academic research and scientific papers

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

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.

Method for synthesizing 1,2-disulfide-3-thioketone derivative by using copper to catalyze

The invention relates to a method for synthesizing 1,2-disulfide-3-thioketone derivative by copper-catalyzed propargylamine sulfur cyclization, and the method comprises the following steps: N, N-dimethyl-3-phenyl propyl-2-alkynyl-1-amine is taken as a substrate, cuprous chloride, cuprous bromide or cuprous iodide is added into the substrate to serve as a catalyst, potassium phosphate, sodium bicarbonate or sodium acetate is taken as an alkali, elemental sulfur is taken as a sulfur source, stirring reaction is performed in a solvent for 12 hours at the temperature of 100-120 DEG C. The elemental sulfur is used as the sulfur source, and the method has the advantages of simple and easily available raw materials, simple reaction operation, relatively mild conditions, wide substrate universality, relatively high yield and good functional group compatibility.

Copper-Catalyzed Tandem Sulfuration/Annulation of Propargylamines with Sulfur via C-N Bond Cleavage

Copper-catalyzed aerobic oxidative sulfuration and annulation of propargylamines with elemental sulfur is described. The tandem reaction involves C-N bond cleavage and the formation of multiple C-S bonds, affording 1,2-dithiole-3-thiones in good to excellent yields with good functional group tolerance.

1,2-dithio-3-thioketone derivative synthesized by cyclizing of fluorine-sulfur removal of trifluoropropyne via copper catalyzing

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.

Copper-Catalyzed Defluorinative Thioannulation of Trifluoropropynes for the Synthesis of 1,2-Dithiole-3-thiones

A simple and practical strategy for the preparation of 1,2-dithiole-3-thiones via copper-catalyzed defluorinative thioannulation of trifluoropropynes has been developed using elemental sulfur as the sole sulfur source. This reaction displays a wide substrate scope and high functional group tolerance to afford the corresponding S-heterocycles in moderate to good yields and features efficient construction of multiple C?S bonds through C?F bond cleavage of CF3 groups. (Figure presented.).

Switching Selectivity of α-Enolic Dithioesters: One Pot Access to Functionalized 1,2- and 1,3-Dithioles

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.

3H-1,2-DITHIOCYCLOPENTENE-3-THIOKETONE COMPOUNDS AND APPLICATION THEREOF

The present invention relates to the field of medicaments, and in particular relates to 3H-1,2-dithiocyclopentene-3-thione compounds and application thereof. 3H-1,2-dithiocyclopentene-3-thione compounds disclosed by the invention have new structures shown in formula I or formula II. Proved by experiments, 3H-1,2-dithiocyclopentene-3-thione compounds can directly protect neurons in a cellular model, and can significantly restrain excessive inflammatory responses of brain inflammatory cells; and by using 3H-1,2-dithiocyclopentene-3-thione, focal ischemic cerebral infarct volumes of mice can be remarkably reduced in an animal model. Therefore, the invention provides the application of 3H-1,2-dithiocyclopentene-3-thione compounds and pharmaceutically acceptable salts thereof in the preparation of medicaments for preventing or treating cerebral apoplexy diseases.

Convenient one-pot syntheses of 1,2-dithiole-3-thiones and 3-imino-1,2-dithioles from terminal alkynes

The reaction of acetylide anions with carbon disulfide or phenyl isothiocyanate followed by addition of sulfur in the presence of a protonating agent such as a primary amine or alcohol affords 1,2-dithiole-3-thiones or 3-imino-1,2-dithioles in good to excellent yields.

Formation of 5-phenyl-1,2-dithiole-3-thione from molybdenum dithiopropiolato complexes

Molybdenum dithiopropiolato complexes, [(η5-C5 R4R′)Mo(CO)2(η2 -S2CC≡CPh)] (R=H, R′=Me 1a, R=R′=H 1b; R=R′=Me 1c) react with trimethylamine- N -oxide (TMNO · 2H2O) under mild the

Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane

The combination of P4S10 and hexamethyldisiloxane efficiently converts esters, lactones, amides, lactams, and ketones to their corresponding thiono derivatives. In the presence of elemental sulfur, 3-oxoesters are converted to dithiolethiones by this reagent. Yields are comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent.