New approach for post-functionalization of meso-formylporphyrins

Abstract

An approach for the transformation of formyl groups into areneimidazoles at a porphyrin substrate is developed, allowing straightforward design of new polytopic porphyrinoid compounds.

Synthesis, DNA binding mode, singlet oxygen photogeneration and DNA photocleavage activity of ruthenium compounds with porphyrin–imidazo[4,5‐f]phenanthroline conjugated ligand

“…Ruthenium complexes have low toxicity and good water solubility, and can be rapidly excreted in vitro after absorption . From the first antitumor ruthenium complex, cis ‐Ru(DMSO) 4 Cl 2 , to recent HL(RuL 2 Cl 4 ) and (HL) 2 (RuLCl 5 ) (L is a small molecule containing N heterocycles) with great curative effect, and then to representative antitumor NAMI‐A structure, ruthenium complexes have proved to have a wide range of applications …”

“…[12,13] From the first antitumor ruthenium complex, cis-Ru(DMSO) 4 Cl 2 , to recent HL(RuL 2 Cl 4 ) and (HL) 2 (RuLCl 5 ) (L is a small molecule containing N heterocycles) with great curative effect, and then to representative antitumor NAMI-A structure, ruthenium complexes have proved to have a wide range of applications. [14,15] In our previous work, we conjugated 5-(4hydroxyphenyl)-10,15,20-triphenylporphyrin with phenanthroline to form flexible ruthenium compounds and studied their binding mode with DNA. [10] In order to obtain the properties and characteristics of conjugated ligands with ruthenium, we studied from two aspects.…”

Advances in Tetrapyrrolic Chemistry over 2013-2017 of Research group Headed by Full Member of RAS A. Yu. Tsivadze: Highlights on the Occasion of his Anniversary

“…This methodology was used to prepare a set of representatives of this new type of substituted porphyrins. [7] Figure 5. New approach for post-functionalization of mesoformylporphyrins.…”

“…New approach for post-functionalization of mesoformylporphyrins. [7] Suzuki-Miyaura cross-coupling reaction has been used for the synthesis of tricyclic architectures based on trans-A 2 B 2 -porphyrins and bisaminal-protected polyazamacrocycles which are linked directly or by a p-phenylene spacer ( Figure 6). This modular approach allowed the synthesis of ligands with various substituted porphyrin macrocycles and bisaminal-protected tetraazamacrocycles possessing different cavity sizes.…”

DFT Evaluation of Reactivity of β-Substituted meso-Bromoporphyrins towards Nucleophilic Substitution

“…[23] Our current research is focused on the development of approaches for the transformation of the periphery of the porphyrin macrocycle by means of metal-promoted methods [25] as well as condensation and substitution transformations. [26][27][28][29] Thus, we have developed approaches for the preparation of meso-alkoxy-and meso-aryloxyporphyrins by means of nucleophilic substitution reaction [26] and performed the quantum-chemical investigation of its selectivity. [23] Thus, in mentioned work we have shown that the application of B3LYP 6-31G* level of theory for the analysis of the characteristics of frontier orbitals allows to estimate the reaction path of the nucleophilic reaction.…”