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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.

ABSTRACT: 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].

SUBMITTER: Journot G

PROVIDER: S-EPMC3343912 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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.

Project description: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.

| S-EPMC3343950 | biostudies-literature

2-(Benzoyl-amino-meth-yl)pyridinium chloride.

Project description:The title compound, C(13)H(13)N(2)O(+)·Cl(-), (1), was obtained as a colorless crystalline by-product during the synthesis of N-(2-pyridylmeth-yl)benzoyl-amine (2). The C-O bond length of 1.231 (2) Å in the benzoyl unit of (1) is slightly elongated in comparison with isolated C=O double bonds as also observed for (2) [1.237 (2) Å]. The N-C bond length of 1.345 (2) Å in the benzoic acid amide unit indicates the formation of an allylic O-C-N system and is very similar to the N-C bond lengths [1.345 (2) Å] of the pyridyl group. A further delocalization of charge from this allylic system into the phenyl fragment does not occur, which can be deduced from a characterisitc C-C single bond length of 1.499 (2) Å between these fragments. A dimer is formed via N-H⋯Cl hydrogen bonds. The two rings make a dihedral angle of 105.0 (2)°

| S-EPMC2959924 | 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

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

Bis{2-[(2-benzoyl-hydrazin-1-yl-idene)meth-yl]-6-meth-oxy-phenolato}iron(III) chloride monohydrate.

Project description:In the title mononuclear iron(III) complex, [Fe(C(15)H(13)N(2)O(3))(2)]Cl·H(2)O, the Fe(III) atom has a distorted octa-hedral geometry and is six-coordinated by four O atoms and two N atoms from two ligands. In the crystal structure, the complex cations, Cl(-) anions and water mol-ecules are connected into a chain along [100] through N-H?O, O-H?Cl and N-H?Cl hydrogen bonds. Two adjacent chains are linked by O-H?O hydrogen bonds.

| S-EPMC3007077 | 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

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

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

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