Vol 59, No 7 (2023)

The review covers works on the synthesis of porphyrins, including amphiphilic star-shaped ones, which are attracting more and more attention of synthetic scientists. The potential of various types of porphyrins, metalloporphyrins and their derivatives as photosensitizers in photodynamic therapy is discussed. The relationship between the structure of porphyrins and their antimicrobial activity is shown. Polymer-porphyrin systems based on biodegradable polyesters and tetraphenylporphyrins immobilized in their matrix are considered as promising composite materials with bactericidal properties.

The behavior of a representative series of previously unknown N -(5-amino-2-thienyl)- and N -[2-(methylsulfanyl)-1,3-thiazol-5-yl]isothioureas under electron ionization (70 eV) has been studied for the first time. 2-Thienylisothioureas form a fairly stable molecular ion ( I _rel 11-25%), whereas there are no peaks of molecular ions in the mass spectra of 1,3-thiazolylisothioureas. The common direction of the decay of the molecular ion of 2-thienyl- and 1,3-thiazolylisothiourea is the breaking of the C-N bond in the isothiourea fragment with the localization of the charge on the imine nitrogen atom and the formation of the ion [R³SC≡NR²]⁺ ( I _rel 34-100%), and for thienyl derivatives also the ion [ M - R³SC=NR²]⁺ (with the localization of the charge on the amine nitrogen atom). Moreover, the last ion is the main one ( I _rel 91-100%). Peaks of [ M - MeSCN]^+• and [MeSCS]⁺ ions have also been identified in the spectra of 1,3-thiazolylisothioureas, the appearance of which is associated with the decay of the thiazole cycle in a molecular ion. In addition, unlike 2-thienylisothioureas, for the studied 1,3-thiazolylisothioureas, there is a break in the C_het-N bond with the localization of the charge on the thiazole-containing fragment.

A series of 1,3-disubstituted ureas containing pyridine (quinoline) and lipophilic adamantane moieties was synthesized by the reaction of 1,1-dimethyl-3-(hetaryl)ureas with amine hydrochlorides (13 compounds, 53-94% yields). The synthesized compounds differ from each other in the substitution position of the adamantane fragment, the structure of the alkyl linker between the adamantane fragment and the amide group, and the type of heterocyclic substituent. They are potentially targeted inhibitors of human soluble epoxide hydrolase (sEH).

Bicyclo[3.3.1]nonane system is an important structural motif observed in a diverse natural products. Here, we report a concise synthetic route exploiting aldol condensation reactions for construction bicyclo[3.3.1]nonane ring system. Our strategy employes cyclohex-2-enones bearing another carbonyl group in side chain as key structural unit. The reaction showed good results for substrates bearing electron-donating groups in aromatic substituents. Overall, the described synthesis of bicyclo[3.3.1]nona-3,6-dien-2-ones required 2 steps and only 2 building blocks (such as Mannich base and acetoacetic ester) to access desired bicyclic system.

Homo-and cross-coupling products were obtained in an attempt to obtain 2-ethynylnaphthalene from 2-(1-chloroethenyl)maphthalene in a glass reactor contaminated with palladium black nanoparticles on the inner wall. The structure of reaction products was characterized by the GC-MS method.

An approach was developed for the direct C( sp ²)-H-functionalization of phenanthridine with a 1 H -benzotriazole residue, carried out in the presence of Selectfluor® reagent and leading to the formation of a C( sp ²)-N bond. The procedure described in this communication makes it possible to obtain α-(1 H -benzotriazol-1-yl)phenanthridine, which is a valuable synthon for further chemical transformations, in one step and using commercially available substrates and reagents.