Access to basic drugs is a major issue in developing countries. Chagas disease caused by Trypanosoma cruzi paradigmatic example of chronic without an effective treatment. Current treatments based on benznidazole and nifurtimox are expensive, ineffective, toxic. N,N'-Squaramides amide-type compounds that feature both hydrogen bond donor acceptor groups capable multiple interactions with complementary sites. When combined amine carboxylic groups, squaramide have increased solubility therefore...

Here we present the anion binding and transport properties of a series calix[6]arenes decorated on their small rim with either halogen bond or hydrogen donating groups. We show that iodotriazole groups enable highly selective chloride nitrate anions, without protons hydroxide, at rates similar to those observed thiourea squaramide

The ability to control anion transporters with precision is crucial maximise their therapeutic potential while mitigating collateral damage healthy cells. Consequently, there a growing interest in light-regulated transporters, which offer the advantage of spatio-temporal over activity. We have previously reported that chloride transport activity an electron-poor squaramide can be inhibited by UV irradiation (365 nm), probably due photo-transformation transporter. Herein we present series...

A minimalist squaramide-based chemodosimeter for Cu2+ is described. Upon selective chelation to 2, induces the formation of a highly colored zwitterionic radical, which kinetically stable hours. The presence radical confirmed by EPR and ESI-MS. It then possible use reagent 2 visual sensing at neutral pH.

Anion receptors can be used to transport ions across lipid bilayers, which has potential for therapeutic applications. Synthetic bicarbonate transporters are of particular interest, as defects in transmembrane associated with various diseases. However, no convenient method exists directly observe and study the mechanisms involved. Here, an assay is presented that allows kinetics into liposomes monitored great sensitivity. The utilises encapsulated europium(III) complex, exhibits a large...

Abstract New tripodal squaramide‐based hosts have been synthesised and structurally characterised by spectroscopic methods. In 2.5 % (v/v) [D 6 ]DMSO in CDCl 3 , compound 4 formed dimeric assemblies [log K dim =3.68(8)] as demonstrated 1 H NMR spectroscopy UV dilution experiments. AFM SEM analyses revealed the formation of a network bundled fibres, which indicates preferential mechanism for aggregation. These C ‐symmetric exhibited two different mutually exclusive modes binding, each one...

E-4424 (2-(4-[4-(4-chloro-1-pyrazolyl)butyl]-1-piperazinyl)pyrimidine) was shown to be a 5-hydroxytryptamine1A receptor ligand in radioligand binding assays and an vitro guinea pig ileum preparation had both antagonist agonist effects. The antagonist/agonist ratio of greater than the case buspirone ipsapirone. compared diazepam, ipsapirone inhibit behavioral response aversive situation mouse black white test box, rat social interaction marmoset human threat test. acute administration...

Abstract We disclose the results of our investigations on influence that insertion method aryl‐extended calix[4]pyrrole into liposomal membranes exerts their properties as anion carriers. use standard HPTS assay to assess transport show post‐insertion carrier, DMSO solution, assigns better activities “two‐wall” α,α‐aryl‐extended 1 compared “four‐wall” α,α,α,α‐counterpart 2 . Notably, opposite were obtained when carriers pre‐inserted membranes. assign this difference an improved incorporation...

The effect of hydrazones and related functional groups on the anion transport activity thioureas is presented.

Abstract Alkynylation of aryl iodides with propargylic amines has been achieved by means a Sonogashira coupling using “on water” methods. The use less than 0.2 mol% tetrakis(triphenylphosphine)palladium [Pd(PPh 3 ) 4 ] and 1.5 copper(I) iodide [CuI] in the presence diisopropylethylamine (DIPEA) allows to proceed at 95 °C yielding moderate good yields mono‐, bis‐, tris‐aminoalkynylbenzene derivatives.

A novel tertiary squaramido-based reverse-turn module SQ is reported, and its conformational properties are evaluated. This easily incorporated into a α-peptide sequence by conventional solid-phase peptide synthesis. The structure characterization of the hybrid squaramido-peptide 4 described, showing that turn segment induces formation hairpin structures in water through both αSQ- βSQ-turns.

The β-turn unit is one of the most important secondary structure elements in proteins. access to new conformationally controlled foldable modules can afford compounds with interesting bioactivities. Here, we describe a family peptido-squaramide based on considerable potential squaramide as hydrogen bond donor and acceptor well low rotational barrier C-N bond. conformational analysis by NMR these chloroform acetonitrile solution shows that disecondary 4-aminobutyric acid its substituents...

Abstract A copper(II)‐mediated diamination of 1,3‐butadienes is reported. The reaction employs an inorganic base, copper dibromide as a reagent, and saccharin the nitrogen source. proceeds for series under relatively mild conditions with complete selectivity in favor 1,4‐oxidation products.

Bambusurils are macrocyclic molecules that known for their high binding affinity and selectivity toward anions. Here, we present the preparation of two bambusurils bearing fluorinated substituents one carboxylic function. These monofunctionalized were conjugated with crown ether cholesterol units. The resulting conjugates successfully tested in liquid–liquid extraction inorganic salts chloride/bicarbonate transport across lipid bilayers.

Simple, clean and fast photoconversion of aniline-derived squaramides was achieved by flashlight illumination. UV irradiation enabled the photochemical squaramide ring-opening to generate 1,2-bisketenes, which DMSO trapped as nucleophilic oxidant. The only photoproducts isolated were 3,4-arylamino maleic anhydrides, present conformational preferences very different from those their parent squaramides. Similar in MeOH. UV-mediated time-dependent anion transport inhibition demonstrated,...

Small peptides and peptomimetic compounds are valuable tools to probe study biological systems. synthetic peptide analogues adopt a given secondary structure driven by structural modules that organize the compound architecture. Among them, β- α-turn mimetics widely used. This work reports SQ4 SQ5 squaramido-based turn combine tertiary squaramide bonds in their control conformational properties. The efficacy of this combination has been evaluated promote folding peptide-like obtain parallel...

Herein we report the design, synthesis and assessment of first example a squaramide-based self-immolative system triggered by an enzymatic reduction.

Relaying conformational change over several nanometers is central to the function of allosterically regulated proteins. Replicating this mechanism artificially would provide important communication tools, but requires nanometer-sized molecules that reversibly switch between defined shapes in response signaling molecules. In work, 1.8 nm long rigid rod oligo(phenylene-ethynylene)s are scaffolds for switchable multi-squaramide hydrogen-bond relays. Each relay can adopt either a parallel or an...

Aromatic rods functionalised with squaramides form intramolecularly hydrogen-bonded arrays that exhibit cooperative polarisation, an effect increases rod length. Greater polarisation in turn produces stronger intermolecular interactions.

Abstract Invited for the cover of this issue are Dr. Stephen Butler, Hennie Valkenier and co‐workers at Université Libre de Bruxelles, Loughborough University, Masaryk University Bristol. The image depicts transport bicarbonate anions versus spontaneous diffusion CO 2 across lipid bilayer a liposome. Read full text article 10.1002/chem.202100491 .