Search

Nucleophilic substitution of the chlorine atom in 4,5-dichloro-1,2-dithiol-3-one using 1-thio-β-d-glucopyranose and its 2,3,4,6-tetra-O-acetyl derivative in acetonitrile resulted in two new 5-thioglucoside conjugates of 4-chloro-1,2-dithiol-3-one. The obtained thioglucosides showed cancer-preventive properties in a model of mouse epidermal JB6Cl41 P+ cells in soft agar, while one of them manifested antitumor activity in in vivo experiments in CD1 mice on a model of solid Ehrlich carcinoma. Both compounds were shown to inhibit basic AP-1-dependent transcriptional activity in murine JB6 Cl41 luc-AP-1 cells. [ABSTRACT FROM AUTHOR]

Nucleophilic substitution of a chlorine atom in 4,5 dichloro-1,2-dithiole-3-thione with per-O-acetyl-1-mercaptho derivatives of d-glucose, d-galactose, d-mannose, d-xylose, l-arabinose, and d-maltose gave six new acetylthioglycoside conjugates of 4-chloro-1,2-dithiole-3-thione. These thioglycosides were shown to possess cancer preventive activity on the models of JB6 Cl41 P+ mouse epidermal cells and THP-1 human leukemia cells in soft agar, as well as to inhibit the AP-1-dependent transcriptional activity in JB6 Cl41 luc-AP-1 cells, which suggests the possibility of using the new compounds as potential cancer preventive drugs. [ABSTRACT FROM AUTHOR]

The reaction of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine with alcohols and sodium alkoxides was evaluated under various conditions. Depending on the reaction conditions, either alkoxy or hydroxy derivatives of [1,2,5]thiadiazolo[3,4-d]pyridazine can be obtained. 4,7-Di-(dodecyloxy)- and 4,7-di(hexyloxy)[1,2,5]thiadiazolo[3,4-d]pyridazines, which may be of interest as the compounds exhibiting liquid crystalline properties, were synthesized for the first time. [ABSTRACT FROM AUTHOR]

The oxidation of hexane-2,3,4,5-tetraone tetraoxime with dinitrogen tetroxide was studied in different solvents. The primary furoxan ring closure was found to occur involving either two central or two terminal oxime groups to form 4,7-dimethyl[1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide and the previously unknown 4,4′-dimethyl-[3,3′-bi(1,2,5-oxadiazole)] 5,5′-dioxide. The structure of the latter compound was established by X-ray diffraction. [ABSTRACT FROM AUTHOR]

A versatile one-pot synthesis of 4-substituted 3-(nitrooxyalkyl)furoxans by the reaction of 3-alkylfuroxans with a mixture of nitric and sulfuric acids was developed. A plausible mechanism of this unusual transformation was explained in terms of a new Grob-type fragmentation. [ABSTRACT FROM AUTHOR]

One-pot synthesis of 3-chloro-1,2,5-thiadiazoles from monosubstituted glyoximes and sulfur monochloride was developed. [ABSTRACT FROM AUTHOR]

The insight into the behavior of polyiodides under non-ambient conditions can enrich the practical applications due to obtaining materials with adjustable and tunable conducting properties. In this work Raman spectroscopy study in the range 0 - 6.5 GPa has been performed for dithiazolylidene-dithiazolium zigzag polyiodide with N-H…N hydrogen bond. Variations of band positions in the low-wavenumber region of Raman spectra have been attributed to the changes in the anionic part of the unit cell. The association of different interacting polyiodide subunits at pressure above 1.5 GPa leads to the emergence of the bands at 98 and 115 cm -1 due to consistent vibrations in the I 8 2- zigzag. The emergence of the band at 159 cm -1 above 0.28 GPa can be assigned to N-H…N hydrogen bond vibration. The obtained results depict undergoing structure transformations: the stronger are cation…cation and anion…anion interactions the more likely is the observation of conducting properties due to the formation of polyiodide zigzag and strongly-bound hydrogen-bonded fragment., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2021 Elsevier B.V. All rights reserved.)

We report the synthesis of some new polysulfur-nitrogen heterocyclics by cycloaddition reactions to the thioketo group of readily available tricyclic 1,2-dithiole-3-thiones. Thus treatment of bis[1,2]dithiolo[1,4]thiazine ketothione 1 with diaryl nitrile imines generated from hydrazonoyl chlorides 2a-g gave [1,3,4]thiadiazolylidenyl[1,2]dithiolo[1,4]thiazines 4a-g in high yield. Compounds 4a-f, bearing the same substituents in both aryl groups, were stable but the analogous 4g,h with a p-nitrophenyl group on carbon gave the bis[1,2]dithiolo[1,4]thiazine dione 9, probably by cycloreversion and hydrolysis during chromatography. Treatment of 1, the bis[1,2]dithiolopyrrole ketothione 13, and dithione 12 with ethoxycarbonyl azide 11 gave imines 12 and 15 and bisimine 16, respectively, by an alternative fragmentation of the initial cycloadduct in which the 1,2-dithiole ring is retained. Reaction of 1 with TosMIC gave the imino-1,3-dithietane 17.