871-76-1Relevant articles and documents
Powerful Bipodal Anion Transporters Based on Scaffolds That Contain Different Chalcogens
Lang, Chao,Zhang, Xin,Luo, Quan,Dong, Zeyuan,Xu, Jiayun,Liu, Junqiu
, p. 6458 - 6465 (2015/10/19)
A new family of bipodal anion transporters based on chalcogen-containing scaffolds has been designed and synthesized. Though structurally related to the well-studied tripodal anionophores, these molecules are simpler with only two anion-binding sites. However, the activities remain high. Anion transport could be facilitated by the new transporter at an exceptionally low loading of transporter/lipid ratio of 1:500000. This impressive efficiency is comparable with the most active one from the tren-based tripodal series. To investigate influences from different scaffolds and substituent groups, lipophilicity, anion-binding property, and transport activity of each molecule were studied. It was found that the bridge atom has a major impact on transport activities mainly as a result of anion-binding differences. The results also suggest that chalcogen can act as a key structural modulator to develop highly effective anion transporters and optimize their activities. Anion transporters based on chalcogen-containing scaffolds have been designed and synthesized. Their lipophilicities, anion binding properties, and transport activities were investigated in detail. The results suggest that chalcogen can act as a key structural modulator to develop highly effective anion transporters and optimize their activities.
Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels
Yang, Donglai,Arifhodzic, Lejla,Ganellin, C. Robin,Jenkinson, Donald H.
supporting information, p. 907 - 923 (2013/07/27)
Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.
A mild and highly convenient chemoselective alkylation of thiols using Cs2CO3-TBAI
Salvatore, Ralph Nicholas,Smith, Robert A.,Nischwitz, Adam K.,Gavin, Terrence
, p. 8931 - 8935 (2007/10/03)
A mild and improved method for the synthesis of thioethers has been developed. In the presence of cesium carbonate, tetrabutylammonium iodide, and DMF, various alkyl and aryl thiols underwent S-alkylation to afford structurally diverse sulfides in high yield. Unprotected mercaptoalcohols and thioamines reacted chemoselectively at the sulfur moiety exclusively. An example of a one-pot, solid-phase synthesis of a thioether is also described.
