Synthesis and antimycotic activity of new derivatives of imidazo[1,2-]pyrimidines.

The heterocyclic core of imidazo[1,2-]pyrimidine was formed in satisfactory yields as a result of the interaction of the readily available 2-aminoimidazole with -substituted maleimides or -arylitaconimides. The mechanism of the studied processes was postulated basing on experimental data, HPLC-MS analysis of reaction mixtures, and quantum chemical calculations. Molecular docking results of the obtained imidazo[1,2-]pyrimidines, when compared with voriconazole, a drug already in clinical use, suggest that they may possess antifungal activity against .

Application of the intramolecular Diels-Alder vinylarene (IMDAV) reaction for the synthesis of benzo-, carbocyclo-, thienothiopheneisoindolecarboxylic acids and its limitations.

Thienylallylamines, readily accessible from the corresponding thienyl aldehydes, react with maleic and trifluoromethylmaleic anhydrides leading to the formation of acids with a thieno[2,3-]isoindole core. The reaction sequence involves two successive steps: acylation of the nitrogen atom of the initial allylamine and the intramolecular Diels-Alder vinylarene (IMDAV) reaction. The scope and limitations of the proposed method were thoroughly investigated.

One-Pot Reaction Sequence: -Acylation/Pictet-Spengler Reaction/Intramolecular [4 + 2] Cycloaddition/Aromatization in the Synthesis of β-Carboline Alkaloid Analogues.

One-pot synthesis of tetrahydro-β-carbolines, fused with an isoindole core, was proposed starting from maleic anhydride and azomethines easily available from tryptamines and 3-(hetaryl)acroleins. This sequence includes four key steps: an acylation of the aldimine with maleic anhydride, a Pictet-Spengler cyclization, an intramolecular Diels-Alder reaction, and a concluding [1,3]- shift. As a result, six- or seven-nuclear alkaloid-like heterocyclic systems, containing a benzo[1,2]indolizino[8,7-]indole fragment annulated with furan, thiophene, or pyrrole, are formed in a diastereoselective manner.

Terpyridine isomerism as a tool for tuning red-to-NIR emissive properties in heteronuclear gold(I)-thallium(I) complexes.

The polymeric linear chain [AuTl(CCl)] reacts with three terpyridine-type ligands substituted with thiophene groups containing N-donor centres in different relative positions (L1, L2 and L3), leading to the Au(I)/Tl(I) complexes [AuTl(CCl)(L1)] (1), [{AuTl(CCl)}(L2)] (2) and [AuTl(CCl)(L3)] (3). X-Ray diffraction studies reveal that L1 acts as a chelate, while L2 and L3 act as bridging ligands, resulting in different coordination indexes for the thallium(I) centre. These structural differences strongly influence their optical properties, and while compounds 2 and 3 emit near the limit of the visible range, complex 1 emits in the infrared region.

Synthesis and antiglycation activity of 3-phenacyl substituted thiazolium salts, new analogs of Alagebrium.

After preliminary ab initio calculations, 3-phenacyl substituted thiazolium salts, analogs of Alagebrium, were synthesized and investigated in vitro as glycation reaction inhibitors. The most part of investigations focused on the potential of the title compounds to attenuate the formation of fluorescent AGEs as well on their ability to disrupt the cross-linking formation among glycated proteins. Additionally, the capability of thiazolium salts to deglycate in the reaction of early glycation products with nitroblue tetrazolium was determined.

Domino Three-Component -Acylation/[4 + 2] Cycloaddition/Alder-ene Synthesis of Polysubstituted Benzo[]isoindole-4-carboxylic Acids.

Diversely substituted, partially saturated benzo[]isoindole-4-carboxylic acids were synthesized by a new three-component reaction (3CR) starting from cinnamic amines (3-arylallylamines), maleimides, and maleic anhydride. The process consists of -acylation of the amines by maleic anhydride, intramolecular [4 + 2] cycloaddition in vinylarenes (the IMDAV reaction), and the concluding Alder-ene reaction between Diels-Alder intermediates and maleimides. All of the reaction steps proceed in a highly regio- and stereoselective manner, furnishing five adjacent chiral centers and leading to a single diastereoisomer of the title compound.

Benzenesulfonamide Analogs: Synthesis, Anti-GBM Activity and Pharmacoprofiling.

The tropomyosin receptor kinase A (TrkA) family of receptor tyrosine kinases (RTKs) emerge as a potential target for glioblastoma (GBM) treatment. Benzenesulfonamide analogs were identified as kinase inhibitors possessing promising anticancer properties. In the present work, four known and two novel benzenesulfonamide derivatives were synthesized, and their inhibitory activities in TrkA overexpressing cells, U87 and MEF cells were investigated.

Benzophenone glass, supercooled liquid, and crystals: elastic properties and phase transitions.

The elastic properties of glass α- and β-modifications of benzophenone (CH)CO are determined for the first time by the ultrasonic method at high pressures up to 1 GPa and in the temperature range of 77 K< < 293 K. Four states of benzophenone are experimentally observed in the investigated temperature range of 77-293 K: glass, supercooled liquid, and α- and β-crystalline phases. The boundaries of phase transitions during isobaric heating are determined.

Influence of Substituents in a Six-Membered Chelate Ring of HG-Type Complexes Containing an N→Ru Bond on Their Stability and Catalytic Activity.

An efficient approach to the synthesis of olefin metathesis HG-type catalysts containing an N→Ru bond in a six-membered chelate ring was proposed. For the most part, these ruthenium chelates can be prepared easily and in high yields based on the interaction between 2-vinylbenzylamines and (the common precursor for Ru-complex synthesis). It was demonstrated that the increase of the steric volume of substituents attached to the nitrogen atom and in the α-position of the benzylidene fragment leads to a dramatic decrease in the stability of the target ruthenium complexes.

Synthesis, In Silico and In Vivo Toxicity Assessment of Functionalized Pyridophenanthridinones via Sequential MW-Assisted Intramolecular Friedel-Crafts Alkylation and Direct C-H Arylation.

A rapid, efficient, and original synthesis of novel pyrido[3,2,1-]phenanthridin-6-ones is reported. First, the key cinnamamide intermediates - were easily prepared from commercial substituted anilines, cinnamic acid, and 2-bromobenzylbromide in a tandem amidation and -alkylation protocol. Then, these -aryl--(2-bromobenzyl) cinnamamides - were subjected to a TFA-mediated intramolecular Friedel-Crafts alkylation followed by a Pd-catalyzed direct C-H arylation to obtain a series of potentially bioactive 4-phenyl-4,5-dihydro-6,8-pyrido[3,2,1-]phenanthridin-6-one derivatives - in good yields.

Correction: Mahmoudi et al. Solvent-Induced Formation of Novel Ni(II) Complexes Derived from Bis-Thiosemicarbazone Ligand: An Insight from Experimental and Theoretical Investigations. 2021, , 5337.

We received a complaint from the Université Catholique de Louvain [...

Correction: Solvent-driven azide-induced mononuclear discrete one-dimensional polymeric aromatic Möbius cadmium(II) complexes of an N tetradentate helical ligand.

Correction for 'Solvent-driven azide-induced mononuclear discrete one-dimensional polymeric aromatic Möbius cadmium(II) complexes of an N tetradentate helical ligand' by Farhad Akbari Afkhami , , 2017, , 14888-14896, https://doi.org/10.1039/C7DT02952G.

Correction: On the importance of π-hole spodium bonding in tricoordinated Hg complexes.

Correction for 'On the importance of π-hole spodium bonding in tricoordinated Hg complexes' by Ghodrat Mahmoudi , , 2020, , 17547-17551, https://doi.org/10.1039/D0DT03938A.

Hyperbaric reactions in organic synthesis. Progress from 2006 to 2021.

This comprehensive review summarizes the published literature data concerning above 1 kbar reactions for the purposes of preparative organic synthesis (more than 50 mg of the initial substance) from 2006 to the beginning of 2021 and highlights the obstacles, which were overcome by the use of a high-pressure technique. The review covers around 100 references.

On the nature of recurrent Au⋯π motifs in tris(2,2'-bipyridine)M(II) (M = Fe, Co and Ni) dicyanoaurate(I) salts: X-ray analysis and theoretical rationalization.

This manuscript reports the synthesis, X-ray characterization and DFT study of three new [M(bipy)][Au(CN)](X) (M = Fe, Co, and Ni; bipy = 2,2'-bipyridine; X = anion) ionic compounds. These salts are composed of [M(bipy)] dications and [Au(CN)] anions in a 2 : 3 ratio. The positive charge is compensated by X = Cl anions in compounds 1 (M = Fe) and 2 (M = Co) and X = OH in 3 (M = Ni).

Evaluation of the antitumor activity of a series of the pincer-type metallocomplexes produced from isonicotinohydrazide derivative.

In this work we report on the antitumor properties of a series of pincer-type metallocomplexes [Hg(HL-keto)Cl] (1), [Hg(HL-keto)I] (2) and [Mn(HL-zwitterion)Cl]∙MeOH (3∙MeOH), derived from N'-(1-(pyridin-2-yl)ethylidene)isonicotinohydrazide (HL) and corresponding metal salts. The Hg(II) and Mn(II) salts are chelated by the keto (HL-keto) or zwitterionic (HL-zwitterion) form of HL, respectively. The cytotoxic effects of these compounds have been accessed against lung adenocarcinoma (A549) and hepatocellular carcinoma (HepG2 and Huh7) cell lines.

Solvent-Induced Formation of Novel Ni(II) Complexes Derived from Bis-Thiosemicarbazone Ligand: An Insight from Experimental and Theoretical Investigations.

In this work, we report solvent-induced complexation properties of a new NS tetradentate bis-thiosemicarbazone ligand (), prepared by the condensation of 4-phenylthiosemicarbazide with bis-aldehyde, namely 2,2'-(ethane-1,2-diylbis(oxy)dibenzaldehyde, towards nickel(II). Using ethanol as a reaction medium allowed the isolation of a discrete mononuclear homoleptic complex (), for which its crystal structure contains three independent molecules, namely , and , in the asymmetric unit. The doubly deprotonated ligand in the structure of is coordinated in a cis-manner through the azomethine nitrogen atoms and the thiocarbonyl sulfur atoms.

New iridium bis-terpyridine complexes: synthesis, characterization, antibiofilm and anticancer potentials.

This study represents synthesis, characterization, screening of antibiofilm efficacy, and cytotoxicity of iridium bis-terpyridine complexes. The complexes were characterized by NMR, MS, FTIR, UV/Visible, and fluorescence spectroscopies. The efficacy of biofilm inhibition and eradication of iridium complexes was evaluated using a crystal violet assay test and verified by fluorescence microscopy.

New class of hantaan virus inhibitors based on conjugation of the isoindole fragment to (+)-camphor or (-)-fenchone hydrazonesv.

This work presents the design and synthesis of camphor, fenchone, and norcamphor N-acylhydrazone derivatives as a new class of inhibitors of the Hantaan virus, which causes haemorrhagic fever with renal syndrome (HFRS). A cytopathic model was developed for testing chemotherapeutics against the Hantaan virus, strain 76-118. In addition, a study of the antiviral activity was carried out using a pseudoviral system.

On the importance of π-hole spodium bonding in tricoordinated Hg complexes.

A new coordination polymer [Hg(LI)I]n (1) and a new discrete coordination complex [Hg(HLII)I2] (2) are synthesized and X-ray characterized. The existence of positive π-holes at the spodium atoms in both compounds is evidenced by DFT calculations. In 1, a Hg-S semicoordination bond and a HgI spodium bond are formed at opposite sides of the π-hole.

Application of New Efficient Hoveyda-Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[]furo[2,3-]pyrroles.

The ring rearrangement metathesis (RRM) of a - diastereomer mixture of methyl 3-allyl-3a,6-epoxyisoindole-7-carboxylates derived from cheap, accessible and renewable furan-based precursors in the presence of a new class of Hoveyda-Grubbs-type catalysts, comprising an N→Ru coordinate bond in a six-membered ring, results in the difficult-to-obtain natural product-like cyclopenta[]furo[2,3-]pyrroles. In this process, only one diastereomer with a -arrangement of the 3-allyl fragment relative to the 3a,6-epoxy bridge enters into the rearrangement, while the -isomers polymerize almost completely under the same conditions. The tested catalysts are active in the temperature range from 60 to 120 °C at a concentration of 0.

Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group.

N-t-Bu-N',N''-Disulfonamide-1,3,5-triazinanes were synthesized and characterized by X-ray single crystal structure analysis. In the course of the X-ray structure elucidation, the first solid experimental evidence of the axial position of the tert-butyl group in unconstrained hexahydro-1,3,5-triazacyclohexanes was obtained. Dynamic low-temperature NMR analysis allowed to fully investigate a rare case of crystallization-driven unanchoring of the tert-butyl group in the chair conformation of saturated six-membered cycles.

Lead(ii) coordination polymers driven by pyridine-hydrazine donors: from anion-guided self-assembly to structural features.

In this work, we report extensive experimental and theoretical investigations on a new series of PbII coordination polymers exhibiting extended supramolecular architectures, namely [Pb2(LI)(NCS)4]n (1), [Pb(HLII)I2]n (2), [Pb(LIII)I]n (3) and [Pb(HLIV)(NO3)2]n·nMeOH (4), which were self-assembled from different PbII salts and various pyridine-hydrazine based linkers, namely 1,2-bis(pyridin-3-ylmethylene)hydrazine (LI), (pyridin-4-ylmethylene)isonicotinohydrazide (HLII), 1-(pyridin-2-yl)ethylidenenicotinohydrazide (HLIII) and phenyl(pyridin-2-yl)methylenenicotinohydrazide (HLIV), respectively. It is recognized that the origin of self-assembling is fundamentally rooted in a dual donor (6s2/6p0 hybridized lone electron pair) and electrophilic behaviour of PbII. This allows production of extended topologies from a 1D polymeric chain in 4 through a 2D layer in 2 to the 3D frameworks in 1 and 3, predominantly due to the cooperative action of both covalent and non-covalent tetrel interactions of the overall type Pb-X (X = O, N, S, I).

Zigzag vs Helicoidal Gold-Silver 1D Chains: Influence of Subtle Interactions in the Spatial Arrangement of Supramolecular Systems.

The reaction of 4'-(2-thienyl)-2,2':6',2,2''-terpyridine (S-terpy) with the heterometallic complexes [AuAgR(OEt)] (R = CF, CCl) leads to the compounds [{Au(CX)}Ag(S-terpy)] (X = F (), Cl ()). The X-ray diffraction analysis of the complexes shows an alternating disposition of the metals -Au-Ag-Au-Ag- in 1D infinite polymeric chains. Despite the fact of having the same metallic sequence, the spatial arrangement observed for both complexes is very different, since for [{Au(CF)}Ag(S-terpy)] () the metals adopt a zigzag disposition, whereas an helicoidal distribution of the interacting metals is observed for the complex [{Au(CCl)}Ag(S-terpy)] ().