81385-76-4

Upstream product

• 25361-94-8 2,3-bis(4-methoxyphenyl)cyclopropenone 
• 35564-24-0 4,5-bis(4-methoxyphenyl)-3H-1,2-dithiole-3-thione 
• 13232-76-3 4,5-diphenyl-[1,2]dithiole-3-thione 

Relevant academic research and scientific papers

Synthesis, characterization, and oxidation electrochemistry of some novel 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones containing aryl and metallocenyl fragments

A new synthesis method was established for 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones, from different cyclopropenones: diphenyl (a), bis-(4-methoxyphenyl (b), diferrocenyl (c) and diruthenocenyl (d), in the presence of elemental sulfur with yields of the 5a-d (35–57%), or in the presence of the additive NaHS, with yields of the 5a-d (45–72%) and 6a-d (10–18%). The characterization of the new compounds was conducted by IR, 1H and 13C NMR spectroscopy, elemental analysis, mass-spectrometry. In addition, X-ray crystallographic analysis of the compounds 5a,b,d was conducted. The redox properties of the heterocyclic compounds were investigated using cyclic (CV), differential pulse (DPV) and square wave (SWV) voltammetries.

Diaryl-dithiolanes and -isothiazoles: COX-1/COX-2 and 5-LOX-inhibitory, {radical dot}OH scavenging and anti-adhesive activities

Three series of non-steroidal anti-inflammatory drugs (NSAIDs) inhibiting the cyclooxygenase/5-lipoxygenase (COX/5-LOX) pathways as such as formation of hydroxyl radicals and adhesion were prepared: 4,5-diaryl isothiazoles, 4,5-diaryl 3H-1,2-dithiole-3-thiones and 4,5-diaryl 3H-1,2-dithiole-3-ones. The aim of the present study was to develop substances which can intervene into the inflammatory processes via different mechanisms of action as multiple target non-steroidal anti-inflammatory drugs (MTNSAIDs) with increased anti-inflammatory potential. The current lead 11a was evaluated in COX-1/2, 5-LOX and {radical dot}OH scavenging in vitro assays and in a static adhesion assay where it proved to inhibit adhesion. Moreover, 11a treatment attenuated expression of macrophage adhesion molecule-1 (Mac-1) on extravasated polymorphonuclear leukocytes (PMNs) which indicates that the activation was reduced. The assays used are predictive for the in vivo efficacy of test compounds as shown for 11a in a peritonitis model of acute inflammation in mice. Thus, the novel 5-LOX/COX and {radical dot}OH inhibitor 11a possesses anti-inflammatory activity that, in addition to COX/5-LOX inhibition, implicates effects on leukocyte-endothelial interactions.

1,1',2,2'-Tetrathiafulvalenes, IV. - On the Reactions of Cyclopropen(thio)nes with 1,2-Dithiole Compounds: Thienothiophenes, Thienofurans, 4H-Furopyrroles, 1,2-Dithiole-3-(thi)ones, and other Heterocycles Containing Sulfur

4,5-Disubstituted 1,2-dithiole-3-thiones (1,2-trithiones) 1 react with 2,3-diphenylcyclopropenethione (2a) to give by elimination of two atoms sulfur thienothiophenes 5.The reaction of 1a with 2a yields in addition tetraphenylthieno-1,2-dithiin (6a). 1,2-Trithiones react with 2,3-diarylcyclopropenones 7 (R3=Aryl) to give the corresponding thienofurans 8 and 1,2-dithiole-3-ones 9. - In 4-position unsubstituted 5-aryl-1,2-trithiones and 2,3-diarylcyclopropenones 7 (R3=Aryl) react in a more complex manner.In the reaction of 4,5-disubstituted 3-phenylimino-1,2-dithiole-3-thiones 18 with 7 (R3=Aryl) 4H-Furopyrroles 19 are formed. - Furthermore it will be reported on conversions of 5-phenyl-3H-1,2,4-dithiazole-3-thione (24), 2-benzyl-4-methyl-3-phenyl-1,2-thiazole-5(2H)-thione (27a), and 2-benzyl-4-phenyl-1,2-thiazole-5(2H)-thione (27b) in the reactions with the cyclopropenones 7d respective 7a.