171614-40-7Relevant articles and documents
Acetic anhydride mediated condensation of aromatic o-diacid dichlorides with benzimidazoles to provide electro-reducible p-dione adducts
Joyce, Eamonn,Kavanagh, Paul,Leech, Dónal,Karpinska, Jolanta,McArdle, Patrick,Aldabbagh, Fawaz
, p. 3788 - 3791 (2012)
Acetic anhydride mediates a facile and rapid condensation of benzimidazole with aromatic o-diacid dichlorides to precipitate p-dione adducts in excellent yields. Condensation with pyridine-3,4-dicarbonyl dichloride produced a 1:1 mixture of isomeric p-diones. The X-ray crystal structure of one of the latter isomers revealed unusual high density, and inter-layer separation similar to graphite. Cyclic voltammetry demonstrated that p-dione is capable of two consecutive one-electron-reductions with formal potentials influenced by the fused (hetero)aromatic and substituent effects.
Synthesis of 1,3,4-oxadiazoles as selective T-type calcium channel inhibitors
Zhang, Man,Zou, Bende,Gunaratna, Medha J.,Weerasekara, Sahani,Tong, Zongbo,Nguyen, Thi D.T.,Koldas, Serkan,Cao, William S.,Pascual, Conrado,Xie, Xinmin Simon,Hua, Duy H.
, p. 145 - 164 (2020/02/04)
– Neuropathic pain, epilepsy, insomnia, and tremor disorder may arrive from an increase of intracellular Ca2+ concentration through a dysfunction of T-type Ca2+ channels. Thus, T-type calcium channels could be a target in drug discovery for the treatments of neuropathic pain and epilepsy. From rational drug design approach, a group of 2,5-disubstituted 1,3,4-oxadiazole molecules was synthesized and their selective T-type channel inhibitions were evaluated. The synthetic strategy consists of a short sequence of three reactions: (i) condensation of thiosemicarbazide with acid chlorides; (ii) ring closing by 1,3-dibromo-5,5-dimethylhydantoin; and (iii) coupling with various acid chlorides. 5-Chloro-N-(5-phenyl-1,3,4-oxadiazol-2-yl)thiophene-2-carboxamide (11) was found to selectively inhibit T-type Ca2+ channel over Na+ and K+ channels in mouse dorsal root ganglion neurons and/or human embryonic kidney (HEK)-293 cells and to suppress seizure-induced death in mouse model. Consequently, compound 11 is a useful probe for investigation of physiologic and pathophysiologic roles of the T-channel, and provides a basis to develop a novel therapeutic to treat chronic neuropathic and inflammatory pains.
Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide
Camelio, Andrew M.,Liang, Yong,Eliasen, Anders M.,Johnson, Trevor C.,Yuan, Changxia,Schuppe, Alex W.,Houk,Siegel, Dionicio
, p. 8084 - 8095 (2015/09/01)
The oxidation of arenes by the reagent phthaloyl peroxide provides a new method for the synthesis of phenols. A new, more reactive arene oxidizing reagent, 4,5-dichlorophthaloyl peroxide, computationally predicted and experimentally determined to possess enhanced reactivity, has expanded the scope of the reaction while maintaining a high level of tolerance for diverse functional groups. The reaction proceeds through a novel "reverse-rebound" mechanism with diradical intermediates. Mechanistic insight was achieved through isolation and characterization of minor byproducts, determination of linear free energy correlations, and computational analysis of substituent effects of arenes, each of which provided additional support for the reaction proceeding through the diradical pathway.
