One‐pot three‐component preparation of novel selenium‐containing spiroketals

Abstract

The one-pot three-component preparation of novel selenium-containing spiroketals with potential biological activity is described. When in situ prepared selenium dichloride is reacted with either propargyl or homopropargyl alcohols in the presence of acetone, two competitive reactions take place, namely 1,2-addition to the triple bond with the formation of the corresponding functionalized divinyl selenides in a completely regio-and stereospecific manner and selenylation at the a-position of the ketone, leading to the novel selenium-containing spiroketals. An alternative approach to the synthesis of the selenium-containing spiroketals with substantial increase of the chemical yield involves the reaction of alkynyl acetals with SeCl 2 . The structure of (4E,11E)-4,11-bis(chloromethylene)-1,8-dioxa-5,12-diselenaspiro[6.6] tridecane was unambiguously confirmed by X-ray analysis. These novel selenium-containing spiroketals were tested for regulation of glucose uptake in L6 myotubes. * Figure 5. Stimulatory effect of 3 on rate of glucose uptake in L6 myotubes. Myotube cultures were washed and received fresh a-MEM supplemented with 2% (v/v) FCS, 22.5. The myotubes were incubated for the 5 h. Control myotubes were untreated, and DMSO-treated myotubes received the vehicle only. The cultures were then taken for the dGlc uptake assay. Mean AE SEM. Statistical significance (p < 0.05) was calculated among experimental groups using the two-tailed Student's t test, *p < 0.05, in comparison to the respective controls, n = 3 S. BRAVERMAN ET AL.wileyonlinelibrary.com/journal/poc

Synthesis and Mechanism of Hypoglycemic Activity of Benzothiazole Derivatives

“…L6 myotubes were maintained as previously described. 39 All experiments were conducted on fully differentiated myotubes.…”

Room-Temperature Metal-Free Multicomponent Polymerizations of Elemental Selenium toward Stable Alicyclic Poly(oxaselenolane)s with High Refractive Index

“…Of all the organoselenium compounds, selenium-containing aliphatic heterocycles with potential biological activity and therapeutic benefits , are an important group, which possess major differences in solubility, stability, chemical properties, optical properties, and so on, compared with acyclic organoselenium compounds and aromatic heterocycles such as selenophenes, and could introduce unique properties and functionalities to polymer materials. However, there has been rare report about polymer structures with selenium-containing aliphatic heterocycles.…”