Novel Aspects of Corrole Chemistry

Nardis, Sara; Monti, Donato; Paolesse, Roberto

doi:10.2174/157019305774322716

Cited by 147 publications

(71 citation statements)

References 49 publications

(83 reference statements)

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“…For the synthesis of corroles 8, 9, and 12-15, the key step was the alkylation of phenol in the presence of a strong base. [20] To avoid alkylation of the inner nitrogen atom of the corrole, a metal-protected core is necessary. Furthermore, it has been reported that manganese and copper derivatives are good at stabilizing corroles and have good biological activities.…”

Section: Resultsmentioning

confidence: 99%

Cationic Metal–Corrole Complexes: Design, Synthesis, and Properties of Guanine‐Quadruplex Stabilizers

Zhang

Weng

et al. 2008

Chemistry A European J

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A series of pyridinium and quaternary ammonium copper corroles has been designed and synthesized. All new compounds have been fully characterized by NMR spectroscopy, high-resolution mass spectrometry, UV/Vis spectrscopy, and elemental analysis. Biochemical studies have indicated that all of these corrole derivatives can stabilize G-quadruplex structures, with corrole 4 being the most effective according to the results of circular dichroism (CD) melting experiments, polymerase chain reaction (PCR) stop assays, and surface plasmon resonance (SPR) experiments. Moreover, both corroles 3 and 4 tend to induce the human telomeric sequence to form hybrid G-quadruplex structures, whereas corroles 8 and 9 are more inclined to induce the human telomeric sequence to form antiparallel G-quadruplex structures.

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Section: Resultsmentioning

confidence: 99%

Cationic Metal–Corrole Complexes: Design, Synthesis, and Properties of Guanine‐Quadruplex Stabilizers

Zhang

Weng

et al. 2008

Chemistry A European J

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“…4,6,15–17 The iron complexes were then prepared following two similar procedures, referred to as Method A and Method B, which differ from each other by the amount of iron chloride in the nitration reaction medium.…”

Section: Methodsmentioning

confidence: 99%

β-Nitro Derivatives of Iron Corrolates

et al. 2012

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Two different methods for the regioselective nitration of different meso-triarylcorroles leading to the corresponding β-substituted nitrocorrole iron complexes have been developed. A two-step procedure affords three Fe(III) nitrosyl products - the unsubstituted corrole, the 3-nitrocorrole and the 3,17-dinitrocorrole. In contrast, a one-pot synthetic approach drives the reaction almost exclusively to formation of the iron nitrosyl 3,17-dinitrocorrole. Electron-releasing substituents on the meso-aryl groups of the triarylcorroles induce higher yields and longer reaction times than what is observed for the synthesis of similar triarylcorroles with electron-withdrawing functionalities, and these results can be confidently attributed to the facile formation and stabilization of an intermediate iron corrole π-cation radical. Electron-withdrawing substituents on the meso-aryl groups of triarylcorrole also seem to labilize the axial nitrosyl group which, in the case of the pentafluorophenylcorrole derivative, results in the direct formation of a disubstituted iron μ-oxo dimer complex. The influence of meso-aryl substituents on the progress and products of the nitration reaction was investigated. In addition, to elucidate the most important factors which influence the redox reactivity of these different iron nitrosyl complexes, selected compounds were examined by cyclic voltammetry and thin-layer UV-visible or FTIR spectroelectrochemistry in CH2Cl2.

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“…The synthetic routes for the preparation of corrole are now significantly improved [3, 4], allowing also studies of functionalization of the corrole [5], a fundamental step for exploitation of such a macrocycle in practical applications. The first examples of the potentialities of corrole derivatives in different fields have been reported in the literature [6].…”

Section: Introductionmentioning

confidence: 99%

Synthetic protocols for the nitration of corroles

Pomarico

Fronczek

Nardis

et al. 2011

J. Porphyrins Phthalocyanines

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The modification of peripheral positions of corroles by introduction of nitro groups is an important functionalization of this macrocycle. The nitro substituent strongly influences the corrole behavior leading to the preparation of macrocycles with different properties, which can be of interest for their exploitation as catalysts, sensing layers in chemical sensors or in the field of supramolecular chemistry. In the last few years we have developed different routes for the β-nitration of the corrole ring, and we report here novel synthetic protocols which can allow the formation of tri- and tetranitro derivatives, as demonstrated by X-ray analysis. In all of the methodologies used, the presence of isocorrole species as reaction intermediates was established, which regenerated the corresponding corrole by metal insertion.

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Novel Aspects of Corrole Chemistry

Cited by 147 publications

References 49 publications

Cationic Metal–Corrole Complexes: Design, Synthesis, and Properties of Guanine‐Quadruplex Stabilizers

Cationic Metal–Corrole Complexes: Design, Synthesis, and Properties of Guanine‐Quadruplex Stabilizers

β-Nitro Derivatives of Iron Corrolates

Synthetic protocols for the nitration of corroles

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