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4-Chloro-benzoyl-meso-octa-methyl-calix[2]pyrrolidino[2]pyrrole: an acyl chloride derivative of a partially reduced calix[4] pyrrole.

ABSTRACT: In the title compound, C(35)H(47)ClN(4)O, the two pyrrolidine rings have envelope conformations. The conformation of the macrocycle is stabilized by N-H⋯N hydrogen bonds and a C-H⋯N inter-action. The benzoyl ring is inclined to the adjacent pyrrole ring by 11.66 (11)°, with a centroid-centroid distance of 3.7488 (13) Å. In the crystal, molecules are linked by N-H⋯O hydrogen bonds into helical chains propagating in [010] and C-H⋯O and C-H⋯π interactions are also observed.

SUBMITTER: Journot G

PROVIDER: S-EPMC3343950 | biostudies-literature |

REPOSITORIES: biostudies-literature

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4-Meth-oxy-benzoyl-meso-octa-methyl-calix[2]pyrrolidino[2]pyrrole: an acyl chloride derivative of a partially reduced calix[4]pyrrole.

Project description:In the title compound, C(36)H(50)N(4)O(2), the two pyrrolidine rings have envelope conformations. The conformation of the macrocycle is stabilized by N-H⋯N hydrogen bonds and a C-H⋯N inter-action. The benzoyl ring is inclined to an adjacent pyrrole ring by 6.76 (9)°, with a centroid-to-centroid distance of 3.6285 (10) Å. In the crystal, apart from a C-H⋯O and a C-H⋯π inter-action, mol-ecules are linked via an N-H⋯O hydrogen bond, leading to the formation of helical chains propagating along [010].

| S-EPMC3343912 | biostudies-literature

Calix[4]pyrrole as a chloride anion receptor: solvent and countercation effects.

Project description:The interaction of calixpyrrole with several chloride salts has been studied in the solid state by X-ray crystallography as well as in solution by isothermal titration calorimetry (ITC) and (1)H NMR spectroscopic titrations. The titration results in dimethylsulfoxide, acetonitrile, nitromethane, 1,2-dichloroethane, and dichloromethane, carried out using various chloride salts, specifically tetraethylammonium (TEA), tetrapropylammonium (TPA), tetrabutylammonium (TBA), tetraethylphosphonium (TEP), tetrabutylphosphonium (TBP), and tetraphenylphosphonium (TPhP), showed no dependence on method of measurement. The resulting affinity constants (K(a)), on the other hand, were found to be highly dependent on the choice of solvent with K(a)'s ranging from 10(2)-10(5) M(-1) being recorded in the test solvents used for this study. In dichloromethane, a strong dependence on the countercation was also seen, with the K(a)'s for the interaction with chloride ranging from 10(2)-10(4) M(-1). In the case of TPA, TBA, and TBP, the ITC data could not be fit to a 1:1 binding profile.

| S-EPMC2572717 | biostudies-literature

A photoswitchable strapped calix[4]pyrrole receptor: highly effective chloride binding and release.

Project description:A stiff-stilbene strapped calix[4]pyrrole receptor can be reversibly switched by light between a strong chloride-binding Z-isomer and a very weakly binding E-isomer. The light-induced switching process is monitored by UV-Vis and 1H NMR spectroscopy and chloride binding is studied in detail using both 1H NMR and ITC titrations in DMSO and MeCN. In DMSO, at millimolar concentrations, switching from a fully bound to an almost fully unbound state can be triggered. Quantification of the binding constants in MeCN reveals an extraordinary 8000-fold affinity difference between the Z- and E-isomer. Single crystal X-ray crystallographic analysis gives insight into the structure of the photogenerated E-isomer and the geometry of the chloride-bound receptors is optimized by DFT calculations. The highly effective control of binding affinity demonstrated in this work opens up new prospects for on demand binding and release in extractions and photocontrol of membrane transport processes, among other applications.

| S-EPMC8179391 | biostudies-literature

Separation of Mercury(II) from Industrial Wastewater through Polymer Inclusion Membranes with Calix[4]pyrrole Derivative.

Project description:Polymer membranes with immobilized ligands are encouraging alternatives for the removal of toxic metal ions from aquatic waste streams, including industrial wastewater, in view of their high selectivity, stability, removal efficacy and low energy demands. In this study, polymer inclusion membranes (PIMs) based on cellulose triacetate, with a calix[4]pyrrole derivative as an ion carrier, were tested for their capability to dispose mercury (Hg(II)) ions from industrial wastewater. The impacts were assessed relative to carrier content, the quantity of plasticizer in the membrane, the hydrocholoric acid concentration in the source phase, and the character of the receiving phase on the performance of Hg(II) elimination. Optimally designed PIMs could be an interesting option for the industrial wastewater treatment due to the high removal efficiency of Hg(II) and great repeatability.

| S-EPMC9147343 | biostudies-literature

A novel calix[4]pyrrole derivative as a potential anticancer agent that forms genotoxic adducts with DNA.

Project description:meso-(p-acetamidophenyl)-calix[4]pyrrole 3 was found to exhibit remarkable cytotoxicity towards A549 cancer cells. A comparative study including the isomer of 3 meso-(m-acetamidophenyl)-calix[4]pyrrole 5, as well as molecules containing 'fragments' of these structures, demonstrated that both the calix[4]pyrrole and the acetamidophenyl units are essential for high cytotoxicity. Although calix[4]pyrroles and other anion-complexing ionophores have recently been reported to induce apoptosis by perturbing cellular chloride concentrations, in our study an alternative mechanism has emerged, as proven by the isolation of covalent DNA adducts revealed by the 32P postlabelling technique. Preliminary pharmacokinetic studies indicate that 3 is able to cross the Blood-Brain-Barrier, therefore being a potential drug that could kill primary and brain metastatic cancer cells simultaneously.

| S-EPMC6056420 | biostudies-literature

Ordered co-encapsulation of chloride with polar neutral guests in a tetraurea calix[4]pyrrole dimeric capsule.

Project description:In this work, we describe the stoichiometrically controlled self-assembly process of tetraurea calix[4]pyrrole 1 with a polar neutral guest, trimethylamine N-oxide or beta-alanine betaine, and methyltrioctylammonium chloride (MTOACl) salt into two supramolecular architectures which differ in morphology and stoichiometry. Whereas an equimolar solution of tetraurea calixpyrrole 1, polar guest and MTOACl produces a four-particle inclusion assembly, a mixture of the same components in a 2 : 1 : 1 molar ratio induces the formation of a dimeric capsular assembly displaying multiple guests which are orderly co-encapsulated. The influence of other polar guests and ammonium salts on the self-assembly process is also described.

| S-EPMC6054108 | biostudies-literature

Synthesis of Novel One-Walled <i>meso</i>-Phenylboronic Acid-Functionalized Calix[4]pyrrole: A Highly Sensitive Electrochemical Sensor for Dopamine.

Project description:Facile access to new one-walled meso-substituted phenylboronic acid-functionalized calix[4]pyrrole (C4P) has been revealed for the first time, starting from cost-effective and easily accessible materials. The structures of both the intermediate dipyrromethane (DPM) and the targeted functionalized C4P have been confirmed by means of 1H-NMR, 13C-NMR, IR, and HRMS spectral data. The voltammetric investigations of the functionalized C4P films cast over a glassy carbon electrode (C4P-GCE) clearly establish the redox stability and redox accessibility of the boronic acid functional moiety present in the C4P framework. We demonstrate that the presence of the unique boronic acid functionality in the C4P endows it with an excellent potential for the highly sensitive electrochemical sensing of the neurotransmitter dopamine (DA). A linear correlation between the strength of the Faradaic signals corresponding to the electro-oxidation of DA over C4P-GCE and the concentration of DA was observed in a concentration range as wide as 0.165-2.302 μM. The C4P-GCE has revealed exceptional stability and reproducibility in the electrochemical sensing of DA, with a nanomolar level limit of detection as low as 15 nM.

| S-EPMC9089685 | biostudies-literature

Cesium Halide Ion Pair Recognition by a Pyrrole Strapped Calix[4]pyrrole.

Project description:The binding properties of the pyrrole-strapped calix[4]pyrrole 2 for cesium halide ion pairs were studied via 1H NMR spectroscopic and single crystal X-ray diffraction analyses. Receptor 2 was found to bind CsF, CsCl, and CsBr in the solid state and in chloroform/methanol (4/1, v/v) solution with relatively high affinity as compared with the parent calix[4]pyrrole 1. It was also revealed by solid-liquid extraction experiments that receptor 2 was capable of solubilizing CsF in CDCl3, a medium in which this salt is otherwise insoluble. Single crystal X-ray diffraction analyses and 1H NMR spectroscopic data recorded in 20% CD3OD in CDCl3 provide support for the suggestion that the strap pyrrolic NH proton of 2, as well as those of the calix[4]pyrrole framework, contribute to anion recognition, thus increasing affinity for cesium halide salts relative to the parent system 1. In the solid state, receptor 2 interacts with CsF to form a two dimensional coordination polymer in the presence of methanol. A linear coordination polymer is observed in the case of CsCl and CsBr. Receptor 2 was also found to form a complex with CsF in chloroform/methanol (4/1, v/v) solution, albeit with a different binding mode than is seen in the solid state.

| S-EPMC7286541 | biostudies-literature

Donor-acceptor-stabilised germanium analogues of acid chloride, ester, and acyl pyrrole compounds: synthesis and reactivity.

Project description:Germaacid chloride, germaester, and N-germaacyl pyrrole compounds were not known previously. Therefore, donor-acceptor-stabilised germaacid chloride (i-Bu)2ATIGe(O)(Cl) → B(C6F5)3 (1), germaester (i-Bu)2ATIGe(O)(OSiPh3) → B(C6F5)3 (2), and N-germaacyl pyrrole (i-Bu)2ATIGe(O)(NC4H4) → B(C6F5)3 (3) compounds, with Cl-Ge[double bond, length as m-dash]O, Ph3SiO-Ge[double bond, length as m-dash]O, and C4H4N-Ge[double bond, length as m-dash]O moieties, respectively, are reported here. Germaacid chloride 1 reacts with PhCCLi, KOt-Bu, and RLi (R = Ph, Me) to afford donor-acceptor-stabilised germaynone (i-Bu)2ATIGe(O)(CCPh) → B(C6F5)3 (4), germaester (i-Bu)2ATIGe(O)(Ot-Bu) → B(C6F5)3 (5), and germanone (i-Bu)2ATIGe(O)(R) → B(C6F5)3 (R = Ph 6, Me 7) compounds, respectively. Interconversion between a germaester and a germaacid chloride is achieved; reaction of germaesters 2 and 5 with TMSCl gave germaacid chloride 1, and 1 reacted with Ph3SiOLi and KOt-Bu to produce germaesters 2 and 5. Reaction of N-germaacyl pyrrole 3 with thiophenol produced a donor-acceptor-stabilised germaacyl thioester (i-Bu)2ATIGe(O)(SPh) → B(C6F5)3 (10). Furthermore, the attempted syntheses of germaamides and germacarboxylic acids are also discussed.

| S-EPMC6472437 | biostudies-literature

A chiral "Siamese-Twin" calix[4]pyrrole tetramer.

Project description:We describe our results in the attempted template syntheses of oligomacrocycle calix[4]pyrrole dimer 4, using Hay coupling reaction conditions, tetraalkynyl calix[4]pyrrole 5 as starting material and two bipyridyl N-oxides of different length as templates. We found that the short bis-N-oxide 3 was not an efficient template for the macrocyclization reaction producing an insoluble crude reaction mixture containing exclusively oligomerization and polycondensation products. On the other hand, when we used the long bis-N-oxide 6 as template we obtained a soluble crude reaction mixture in which we did not detect the expected calix[4]pyrrole dimer 4. Instead, we isolated, in low yield, an encapsulation complex of the bis-N-oxide 6 in a partially reacted calix[4]pyrrole dimer. The major isolated species was an unprecedented calix[4]pyrrole tetramer encapsulating two molecules of 6. The complex adopted a chiral helical-like conformation in the solid state resembling the previously described so-called "Siamese-Twin porphyrins".

| S-EPMC6024643 | biostudies-literature

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