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Enaminone Substituted Resorcin[4]arene-Sealing of an Upper-Rim with a Directional System of Hydrogen-Bonds.

ABSTRACT: The paper presents the synthesis of an enaminone resorcin[4]arene via a thermally activated o-quinomethide. The crystal structure indicates that in the solid state all enaminone units participate in a unidirectional seam of 12 intramolecular hydrogen bonds that are formed around the cavity. The molecule exhibits C2 symmetry, with two opposite-laying enaminone units directed inside the cavity ("in"), and the other two units outside the cavity ("out"). In the solution the enaminone resorcin[4]arene exists as a mixture of conformers with distribution controlled by temperature and solvent. The experimental data are compared with the results of theoretical calculations using DFT B3LYP/6-31G(d,p) and fast semi-empirical DFTB/GFN2-xTB method in various solvents.

SUBMITTER: Szafraniec A

PROVIDER: S-EPMC7589316 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Enaminone Substituted Resorcin[4]arene-Sealing of an Upper-Rim with a Directional System of Hydrogen-Bonds.

Szafraniec Anna A Grajda Marcin M Jędrzejewska Hanna H Szumna Agnieszka A Iwanek Waldemar W

International journal of molecular sciences 20201011 20

The paper presents the synthesis of an enaminone resorcin[4]arene via a thermally activated o-quinomethide. The crystal structure indicates that in the solid state all enaminone units participate in a unidirectional seam of 12 intramolecular hydrogen bonds that are formed around the cavity. The molecule exhibits C2 symmetry, with two opposite-laying enaminone units directed inside the cavity ("in"), and the other two units outside the cavity ("out</i ...[more]

PMID: 33050670

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Intramolecular Hydrogen Bond Driven Conformational Selectivity of Coumarin Derivatives of Resorcin[4]arene.

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Theoretical Study of Intramolecular Interactions in Peri-Substituted Naphthalenes: Chalcogen and Hydrogen Bonds.

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Project description:The title compound, C(84)H(112)O(36), has a macrocyclic structure. It has 12 (meth-oxy-carbon-yl)meth-oxy 'head groups' in the upper rim and exhibits a flattened boat geometry. Intra-molecular C-H⋯O hydrogen bonds occur. In the crystal, inter-molecular C-H⋯O contacts occur. The 'head groups' and the pentyl 'feet' contain disordered (0.5:0.5 occupancy ratio) atoms.

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Copper-catalyzed etherification of arene C-H bonds.

Project description:A method for direct, auxiliary-assisted alkoxylation and phenoxylation of ?-sp(2) C-H bonds of benzoic acid derivatives and ?-sp(2) C-H bonds of amine derivatives is reported. The reaction employs (CuOH)2CO3 catalyst, air as an oxidant, phenol or alcohol coupling partner, DMF, pyridine, or DMPU solvent, and K2CO3, tetramethylguanidine, or K3PO4 base at 70-130 °C.

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Project description:Ruthenium(II)-arene complexes are promising drug candidates for therapy of solid tumors. We have previously shown that ruthenium(II)-arene complex [Ru(η6-p-cymene)(L7)Cl] (RuT7) exerts cytotoxic effects in a panel of cancer cell lines (J. Organomet. Chem. 2014, 749, 343–349). In this study we analyzed in vitro cellular response and performed whole-transcriptome microarray gene expression analysis in HeLa cells in order to understand the cellular and molecular mechanism of response to RuT7 complex. Results on biological action of ruthenium complex obtained on cellular level were reflected on molecular level as well. Analysis of functional categories and signaling and biochemical pathways that are associated with HeLa cells' response to ruthenium complex revealed that RuT7 complex leads HeLa cells through intrinsic (mitochondrial) apoptotic pathway, via indirect DNA damage made by action of reactive oxygen species and through direct DNA binding of RuT7. Performed molecular toxicity analysis has shown that RuT7 has fewer associated toxicity profiles than cisplatin. Altogether these results provide the basis for development of RuT7 in animal and pre-clinical studies as a potential drug candidate.

2015-09-11 | GSE72905 | GEO

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