615-20-3Relevant articles and documents
Novel usage of 2-BTSO2CF2H for metal-free electrophilic difluoroalkanethiolation of indoles
Bao, Kun,Hu, Jinbo,Sheng, Rong,Wang, Yuan,Wei, Jun
, p. 4556 - 4559 (2020)
The electrophilic difluoromethylthiolation of indoles with 2-BTSO2CF2H is developed. In the presence of (EtO)2P(O)H and TMSCl, the reaction proceeded under mild conditions to give products in modest to high yields. This is a new application of 2-BTSO2CF2H for electrophilic difluoromethylthiolation.
Deaminative chlorination of aminoheterocycles
Cornella, Josep,Faber, Teresa,Gómez-Palomino, Alejandro,Ghiazza, Clément
, (2021/12/23)
Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]
Synthesis and biological evaluation of heteroarylnonanenitriles as potential antitrypanosomal agents: Serendipitous discovery of novel anticholinesterase hits
Artigas, Albert,Sola, Irene,Taylor, Martin C.,Clos, M. Victòria,Pérez, Belén,Kelly, John M.,Mu?oz-Torrero, Diego
, p. 455 - 461 (2018/05/22)
We have recently developed three antitrypanosomal leads that feature a unit of huprine or (6-chloro-)tacrine linked to a 8-cyanooctyl side chain, which, unfortunately, exhibit very potent (low nanomolar) acetylcholinesterase (AChE) inhibitory activity, which might lead to unwanted cholinergic side-effects. Because huprine and tacrine moieties impart high acetylcholinesterasic potency, we have explored their replacement by alternative heteroaromatic systems (thiazolylbenzamido, quinoxalinecarboxamido, benzimidazolecarboxamido, and benzothiazolylamino moieties), while retaining the 8- cyanooctyl side chain. These structural modifications led to the desired drop in AChE inhibitory activity (low micromolar), albeit at the expense of the antitrypanosomal potency. However, despite the lower AChE inhibitory activity of the novel compounds compared to that of the initial leads, their potency is comparable to that of some AChE inhibitors currently approved for Alzheimer’s disease (AD) treatment. They are brain permeable and less lipophilic than the leads, thereby emerging as interesting novel hits for future AChE inhibitor-based AD drug discovery programs.