
Damian Trzybiński- PhD
- University of Warsaw
Damian Trzybiński
- PhD
- University of Warsaw
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Publications (156)
Pseudoatom databanks, collections of parameters from the multipole model of electron densities for various atom types, are used to replace the Independent Atom Model with the more accurate Transferable Aspherical Atom Model (TAAM) in crystal structure refinements. The databanks are also employed to reconstruct the electron density of a molecule, cr...
Periodic density-functional theory (DFT) calculations were used to predict the thermodynamic stability and the likelihood of interconversion between a series of halogen-bonded cocrystals. The outcomes of mechanochemical transformations were in excellent agreement with the theoretical predictions, demonstrating the power of periodic DFT as a method...
Auranofin, initially developed as a treatment for rheumatoid arthritis, is currently under extensive investigation as a potential drug for various conditions, including cancer, bacterial infections, and parasitic infections. The compound is a known inhibitor of thioredoxin reductase (TXNRD1) and related selenoproteins. Although preliminary studies...
Plants are able to produce various types of crystals through metabolic processes, serving functions ranging from herbivore deterrence to photosynthetic efficiency. However, the structural analysis of these crystals has remained challenging due to their small and often imperfect nature, which renders traditional X-ray diffraction techniques unsuitab...
Armeria maritima is a halophyte exhibiting a strong tolerance to heavy metals. It grows on zinc–lead waste heaps. This study aimed to determine the role of salt glands in the removal of lead (Pb) from plants and to trace the path of lead from the shoots to the salt glands on the surface of leaves. Mechanisms allowing high tolerance to lead in A. ma...
Four isomeric di-6-oxoverdazyl diradicals connected at their N(1) or C(3) positions with either 1,3- or 1,4-phenylene linkers were obtained and characterized by spectroscopic, electrochemical, magnetic, and structural methods. These results were compared to those for the corresponding 6-oxoverdazyl monoradicals. UV–vis spectroscopy demonstrated tha...
Applications of 9-aminoacridine (9aa) and its derivatives span fields such as chemistry, biology, and medicine, including anticancer and antimicrobial activities. Protonation of such molecules can alter their bioavailability as weakly basic drugs like aminoacridines exhibit reduced solubility at high pH levels potentially limiting their effectivene...
Discovery of a halogen-bonded ternary cocrystal of 1,3,5-trifluoro-2,4,6-triodobenzene with pyrazine and triphenylphosphine sulfide has revealed a complex landscape of multicomponent phases, all achievable by mechanochemical interconversion. The observed solid-state reaction...
Discovery of a halogen-bonded ternary cocrystal of 1,3,5-trifluoro-2,4,6-triodobenzene with pyrazine and triphenylphosphine sulfide has revealed a complex landscape of multicomponent phases, all achievable by mechanochemical interconversion. The observed solid-state reaction pathways were explained by periodic density-functional calculations and co...
Cyclic dipeptides with two intramolecular peptide bonds forming a six-membered 2,5-diketopiperazine ring are gaining significant attention due to their biological and chemical properties. Small changes in the local geometry of such molecules (from cis to trans) can lead to significant structural differences. This work presents the results of a stud...
The application of Hirshfeld atom refinement (HAR) fragmentation is demonstrated for the refinement of metal-organic framework (MOF) crystal structures. The presented method enables anisotropic refinement of imidazolate hydrogen atoms, as well as complex analysis of solvent disorder within MOF pores. The data used were derived from standard resolut...
A Cu(II)-salen complex encapsulated in MWW-framework as an efficient chiral organocatalyst was developed for the synthesis of 3,4-dihydropyrimidin-2-(1H)-one (DHPMs) derivatives via an asymmetric pathway. In order to confirm its structural properties, single-crystal X-ray diffraction, powder XRD, BET, XPS, FE-SEM, EDX, UV–Vis, and FTIR spectra were...
The application of Hirshfeld atom refinement (HAR) fragmentation method is demonstrated for the refinement of metal-organic framework (MOF) crystal structures. The presented method enables anisotropic refinement of imidazolate hydrogen atoms, as well as complex analysis of solvent disorder within MOF pores. The data used were derived from standard...
3-Chloro-3-phenylquinoline-2,4-dione (2) is an intermediate product in the synthesis of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione (PhIC). PhIC, its intermediates, and derivatives belong to quinolines or quinazolines - heterocyclic compounds with biological activity. However, only compound 2 contains nitrogen and chlorine atoms in the struc...
3-Chloro-3-phenylquinoline-2,4-dione (2) is an intermediate product in the synthesis of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione (PhIC). PhIC, its intermediates, and derivatives belong to quinolines or quinazolines - heterocyclic compounds with biological activity. However, only compound 2 contains nitrogen and chlorine atoms in the struc...
The nature and strength of interactions for an anti-HIV drug, Lamivudine, were studied in a pure crystal form of the drug and the ligand–receptor complexes. High-resolution single-crystal X-ray diffraction studies of the tetragonal polymorph allowed the drug’s experimental charge density distribution in the solid state to be obtained. The QM/MM cal...
Tolerance to heavy metals in plants is a model process used to study adaptations to extremely unfavorable environments. One species capable of colonizing areas with high contents of heavy metals is Armeria maritima (Mill.) Wild. A. maritima plants growing in metalliferous areas differ in their morphological features and tolerance levels to heavy me...
Periodic density-functional theory (DFT) calculations were used to predict the thermodynamic stability and the likelihood of interconversion between a series of halogen-bonded cocrystals. The outcomes of mechanochemical transformations were in excellent agreement with the theoretical predictions, demonstrating the power of periodic DFT as a method...
The first-in-class luminescent dinucleoside phosphate analogs with a [Re2(μ-Cl)2(CO)6(μ-pyridazine)] "click" linker as a replacement for the natural phosphate group are reported together with the synthesis of luminescent adenosine and thymidine derivatives having the [Re2(μ-Cl)2(CO)6(μ-pyridazine)] entity attached to positions 5' and 3', respective...
Detailed nuclear magnetic resonance (NMR), crystallographic and ab initio studies were performed on derivatives of adenosine and 2’-deoxyadenosine modified with boron clusters or alternatively with a phenyl group at position C8. The conformational study of these compounds showed very good agreement between the results established by these three met...
Water splitting is a promising way to alleviate the energy crisis. In nature, water oxidation is done by a tetranuclear manganese cluster in photosystem II. Therefore, the study of water oxidation by Mn complexes is attractive in water splitting systems. In this report, a new mononuclear Mn(II) complex, MnL2 (HL = (E)-3-hydroxy-Nʹ-(pyridin-2-ylmeth...
In this paper, we describe a method for preparing a monosulfonated dibenzo-24-crown-8 ether, SDB24C8, by direct sulfonation of the parent crown (DB24C8). Since neutral DB24C8 readily interacts with cationic guests, permanently charged SDB24C8 is an advantageous candidate for future supramolecular applications. SDB24C8 can be isolated as a sulfonic...
A new highly fluorescent zinc-organic framework [Zn2(btca)(DMSO)2]n (Zn-MOF) was prepared via in situ ligand formation by the solvothermal reaction of Zn(NO3)2·6H2O and pyromellitic dianhydride (PMDA) in DMSO solvent. During the solvothermal reaction, PMDA was gradually hydrolyzed to a pyromellitic acid, 1,2,4,5-benzene tetracarboxylic acid (H4btca...
Mixed-valence (MV) binuclear ferrocenyl compounds have long been studied as models for testing theories of electron transfer and in attempts to design molecular-scale electronic devices (e.g., molecular wires). In contrary to that, far less attention has been paid to MV binuclear ferrocenes as anticancer agents. Herein, we discuss the synthesis of...
The knowledge pertaining to the chemistry and biological activity of glycol nucleic acid (GNA) components, like nucleosides and nucleotides, is still very limited. Herein we report on the preparation of the uracil nucleoside (1) and nucleotide ester GNA (2). The compounds are functionalised with a luminescent phenanthrenyl group. In DMSO, 1 and 2 a...
Crystal structure of the series of three hexaalkylguanidinium halides (hexa-n-propylguanidinium tri-n-propylguanidinium diiodide (1), hexa-n-butylguanidinium bromide (2) and hexa-n-pentylguanidinium bromide (3) has been revealed and reported for the first time. Investigated hexalkylguanidinium derivatives belong to the group of compounds which find...
Correction for ‘X-ray wavefunction refinement and comprehensive structural studies on bromo-substituted analogues of 2-deoxy- d -glucose in solid state and solution’ by Marcin Ziemniak et al. , RSC Adv. , 2022, 12 , 8345–8360. DOI: 10.1039/D1RA08312K
The structural studies on two bromo-substituted derivatives of 2-deoxy-d-glucose (2-DG), namely 2-deoxy-2-bromo-d-glucose (2-BG) and 2-deoxy-2-bromo-d-mannose (2-BM) are described. 2-DG itself is an inhibitor of hexokinase, the first enzyme in the glycolysis process, playing a vital role in both cancer cell metabolism and viral replication in host...
Pseudoatom databanks, collecting parameters of multipole model of electron densities for various atom types, are used to replace Independent Atom Model by the more accurate Transferable Aspherical Atom Model (TAAM) in crystal structure refinement. They may also be used to reconstruct electron density of a molecule, crystal or biomacromolecular comp...
Herein, a framework for the estimation of the thermodynamic properties of molecular crystals via the refinement of frequencies from density functional theory calculations against X-ray diffraction data is presented. The framework provides an efficient approach to including the contribution of acoustic modes in the thermodynamic properties. The obta...
An investigation of the impact of shape, size and coordination ability of the counter ions was carried out on a five silver(I)- 1, 2- bis (1-methylthioimidazolyl) ethane coordination polymers namely, [Ag2L (NO3)2]n (1), [Ag2L (SO3CF3)2]n (2), {[AgL][ClO4]}n (3), {[AgL]2[BF4]2}n (4) and {[AgL]3[PF6]3}n (5). They have been characterized by the elemen...
The lithium complexes [(WCA‐NHC)Li(toluene)] of anionic N‐heterocyclic carbenes with a weakly coordinating borate moiety (WCA‐NHC, WCA=B(C6F5)3, NHC=IDipp=1,3‐bis(2,6‐diisopropylphenyl)imidazolin‐2‐ylidene) were used for the preparation of silver(I) or copper(I) WCA‐NHC complexes. While the reactions in THF with AgCl or CuCl afforded anionic mono‐...
Two EWG‐activated Hoveyda‐Grubbs‐type ruthenium complexes (Sil‐II and Sil‐II’) were obtained, characterized, and screened in a set of olefin metathesis reactions. These catalysts were conveniently synthesized from a commercially available pharmaceutical building block – Sildenafil aldehyde – in two steps only. Stability and catalytic activity tests...
Two new hybrid organic-inorganic compounds, which incorporate 3,3 0-diammoniumdiphenylsulfone or 4,4 0-diammoniumdiphenylsulfone cations and sulfate anions, were synthesized and analyzed in detail. The crystal structures of both systems were established using single-crystal X-ray diffraction analysis. Crystallographic study revealed that the crysta...
In this paper, we report the Yb(OTf)3‐mediated etherification reaction that allowed obtaining R,R and S,R isomers of ferrocenyl glycol nucleic acid (Fc‐GNA) nucleosides from their corresponding stereo‐defined (S,R) precursor. The R,R absolute configuration of the chiral carbon atoms in one of the Fc‐nucleoside isomers was assigned by single‐crystal...
The results of structural studies on a series of halogen-substituted derivatives of 2-deoxy-D-glucose (2-DG) are reported. 2-DG is an inhibitor of glycolysis, a metabolic pathway crucial for cancer cell proliferation and viral replication in host cells, and interferes with D-glucose and D-mannose metabolism. Thus, 2-DG and its derivatives are consi...
The metal-free reduction of a range of phosphine(V) oxides employing oxalyl chloride as an activating agent and hexachlorodisilane as reducing reagent has been achieved under mild reaction conditions. The method was successfully applied to the reduction of industrial waste byproduct triphenylphosphine(V) oxide, closing the phosphorus cycle to clean...
Phosphodiesterase 5 (PDE5) is one of the most extensively studied phosphodiesterases that is highly specific for cyclic-GMP hydrolysis. PDE5 became a target for drug development based on its efficacy for treatment of erectile dysfunction. In the present study, we synthesized four novel analogues of the phosphodiesterase type 5 (PDE5) inhibitor—tada...
Currently available chemotherapeutic treatments for blood cancers (leukemia) usually have strong side effects. More selective, efficient, and less toxic anticancer agents are needed. We synthesized seven, new, optically pure (12aS)‐1,3,4,12a‐tetrahydropyrazino[2,1‐c][1,4],12(2H,11H)‐dione derivatives and examined their cytotoxicity towards eight ca...
A high-resolution single-crystal X-ray diffraction study of abiraterone acetate (1) has been carried out. The charge density distribution in the crystal of this anticancer drug is reconstructed from experimental data. The nature and the contributions of various intermolecular interactions to the total crystal energy are studied by means of the quan...
In the present paper the structural and dynamical properties of crystalline 2,6–dimethylpyrazine - picric acid cocrystal are described. The title cocrystal crystallizes in centrosymmetric monoclinic P21/c space group. The X-ray diffraction and NMR spectroscopy show the presence of protonated form of 2,6-dimethypyrazine and deprotonated form of picr...
A series of fourteen novel, eight-membered lactam- and dilactam-based analogues of tricyclic drugs were obtained in a simple one-pot procedure. Crystal structures of two compounds were determined by single-crystal X-ray diffraction analysis and their selected structural features were discussed and compared with those of imipramine and dibenzepine....
The synthesis, crystallisation and detailed description of the crystal structure of the THF solvates of four halogen (F, Cl, Br and I) derivatives of dianthranilide (5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione) have been reported. The influence of the halogen size on the conformation of the halogen derivative, the overall supramolecular architectu...
Unsymmetrically N-substituted and N,N’-disubstituted 5,12-dihydrodibenzo [b,f][1,4]diazocine-6,11-diones were synthesized in the new protocol. The desired modifications of the dibenzodiazocine scaffold were introduced at the stages of proper selection of building blocks as well as post-cyclization modifications with alkylation or acylation agents,...
Beneficial structural motifs from two known state-of-the-art olefin metathesis catalysts types, bearing unsymmetrical N-heterocyclic carbenes (uNHCs), were combined into a new hybridized design thereby translating the complementary beneficial reactivity demonstrated by their ‘parent’ complexes to the new N-fluorene derived olefin metathesis catalys...
A series of chlorine‐substituted benzotriazole derivatives, representing all possible substitution patterns of halogen atoms attached to the benzotriazole benzene ring, were synthetized as potential inhibitors of human protein kinase CK2. Basic ADME parameters for the free solutes (hydrophobicity, electronic properties) together with their binding...
Robust, selective, and stable in the presence of ethylene, ruthenium olefin metathesis pre‐catalyst, {[3‐benzyl‐1‐(10‐phenyl‐9‐phenanthryl)]‐2‐imidazolidinylidene}dichloro(o‐isopropoxyphenylmethylene)ruthenium(II), Ru‐3, bearing an unsymetrical N‐heterocyclic carbene (uNHC) ligand, has been synthesized. The initiation rate of Ru‐3 was examined by r...
Ferrocenylated glycol nucleic acid (Fc-GNA) components are rarely studied in the field of xeno nucleic acid (XNA) chemistry. As an attempt to contribute to XNA chemistry, in the present article we report a seven-step synthesis of the first semicanonical dinucleoside containing the Fc-GNA nucleoside linked to the adenosine nucleoside with a phosphod...
A novel approach for the synthesis of unsymmetrically substituted dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones has been developed. This facile three-step method uses variously substituted 1H-benzo[d][1,3]oxazine-2,4-diones (isatoic anhydrides) and 2-aminobenzoic acids as a starting materials. The obtained products were further transformed into N-a...
This work presents results of methyl 7-oxoabiet-13(14)-en-18-oate (3) self-oxidation with air-oxygen in the presence of various bases such as triethylamine or sodium t-butoxide. While under aerobic conditions, the use of sodium t-butoxide as a base results in the formation of four isomeric alcohols, an addition of triethylamine into reaction medium...
High-resolution single-crystal X-ray measurements of the monoclinic polymorph of bicalutamide and the aspherical atom databank approach have served as a basis for a reconstruction of the charge density distribution of the drug and its androgen receptor (AR) and albumin complexes. The contributions of various types of intermolecular interactions to...
The synthesis and biological activity of bioorganometallic conjugates of ciprofloxacin with ferrocenyl, ruthenocenyl and cymantrenyl entities is reported. Their antimicrobial activities were investigated against Gram+ bacteria, Gram ̶ bacteria and bloodstream forms of T. brucei. Furthermore, morphological changes of bacterial cells upon treatment w...
Detailed description of the crystal structure, Hirshfeld Surface analysis and the results of theoretical calculations for three new hybrid inorganic–organic polyoxoselenomolybdate-based systems (C7H10N)4[Se2Mo5O21]·5H2O (1), (C6H8N)4[Se2Mo5O21]·7H2O (2) and (C7H10NO)4[Se2Mo5O21]·3H2O are reported. Title compounds were synthesized using solution met...
Structures of three polymorphs of 1-acetylpyrene were determined using single-crystal X-ray diffraction and their solid state luminescence investigated. While formerly known 1AP-α polymorph, with its herringbone packing motif, is proved to be non-luminescencent, the newly discovered polymorphs β and γ, with crystal structures based on π · · · π-dim...
Glycol nucleic acids (GNA) are synthetic genetic-like polymers with an acyclic three-carbon propylene glycol phosphodiester backbone. Here, the synthesis, luminescence properties, circular dichroism (CD) spectra, and confocal microscopy speciation study in HeLa cells of (R,S) and (S,R) pyrenyl-GNA (pyr-GNA) nucleosides are reported. Enantiomericall...
The synthesis and detailed description of the crystal structure and energetic features of the 1:1 cocrystal of carbamazepine (5H-dibenzo[b,f]azepine-5-carboxamide, CBZ) with 3,5-dinitrobenzoic acid (35DNBA), i.e. C15H12N2O·C7H4N2O6, are reported. The CBZ and 35DNBA molecules are packed in alternately arranged layers. Two characteristic R2²(8) a...
The reaction of 1-phenyl-2H,6H-imidazo[1,5-c]quinazolino-3,5-dione (4) with 3-molar excess ethylene oxide was described. The resulting product was characterized by spectroscopic techniques (¹H-, ¹³C-NMR, IR, and UV) and by X-ray crystallography. It was expected to produce a product of the subsequent reaction in the hydroxyl groups of the initially...
Six new coordination polymers namely, [Ag2L(NO3)2]n (1), {[Ag6L4(CF3SO3)4 ][CF3SO3]2}n (2), {[Ag2L(NO3)][ClO4]}n (3), {[Ag2L(NO3)][BF4]}n (4), {[Ag2L(NO3)][PF6]}n (5) and {[Ag2L(NO3)][SbF6]}n (6) have been successfully synthesized by the reaction of AgNO3 and selected co-anions CF3SO3−, ClO4−, BF4−, PF6− and SbF6− with 1, 3- bis (1-methylthioimidaz...
A series of N‐heterocyclic copper carbene complexes bearing sulfoxide and sulfone moieties have been prepared. In case of new copper compounds with sulfone ligand, the solid‐state structures were determined using X‐Ray crystallography. Obtained complexes were investigated as catalysts in such transformations as: 1,3‐dipolar cycloaddition of alkynes...
This paper presents a report of the synthesis and chemical transformations of anthracene-thymine and 4-thiothymine derivatives. In a reaction of 1-(anthracen-9-yl)-1-hydroxy-3-(N1-thyminyl)-propane with ethylene glycol either an elimination or substitution product is preferentially formed depending on reaction conditions. In the presence of Yb(OTf)...
Thiol-modified ferrocenes on gold have been archetypical model systems for many fundamental charge transfer and other studies, since both thiol-gold and ferrocene redox chemistry are considered to be well-understood. Thus unexpectedly, we found that for a representative of a new class of flexibly linked bis-ferrocenyl compounds, namely, 1-10-bis(1-...
[2]rotaxanes composed of dibenzo-24-crown-8 wheel (DB24C8) and the axle containing two metal-complexing tetraazamacrocyclic units linked with p-xylylene bridge, coordinating the same or different metal ions (Ni and/or Cu) are described. Symmetric di-Ni rotaxane crystallizes in the monoclinic P21/c space group with one rotaxane cation and four PF6−...
The crystal structure and the results of theoretical calculations for the new organoarsenate salt o-anisidinium dihydroarsenate (systematic name: 2-methoxyanilinium dihydrogen arsenate), C7H10NO⁺·H2AsO4⁻, are reported. The salt, crystallizing in the triclinic space group P, was synthesized using a solution method and was characterized by singl...
Four luminescent fac-[Re(CO)3(phen)(L)] complexes with phen = 1,10-phenanthroline and L = non-steroidal anti-inflammatory drug (NSAID) carboxylate ligand were obtained from the reaction of fac-[ReCl(CO)3(phen)] with aspirin, (S)-(+)-ibuprofen, (S)-(+)-naproxen and indomethacin, respectively. Of the four compounds obtained, only fac-[Re(CO)3(phen)(a...
The crystal and molecular structure of the pure (S)-enantiomer of the popular analgesic and anti-inflammatory drug ketoprophen (α-ket) is reported. A detailed aspherical charge-density model based on high-resolution X-ray diffraction data has been refined, yielding a high-precision geometric description and classification of the O—H⋯O interactions...
Azamacrocyclic complex was used as a platform for the construction of the [3]rotaxanes containing two DB24C8 macrocycles per molecule. The complex unit incorporates two electron deficient π-bond systems and two N–H hydrogen bond donoring groups which facilitated formation of a 1:2 interlocked structure. Synthesis and properties of such compounds ar...
A detailed description of the crystal structure and a Hirshfeld surface analysis of the new heteropolyoxometalate compound (C6H8N)5[HAs2Mo6O26(H2O)]·3H2O are reported. The title compound was synthesized using solution methods and its structure was characterized by single-crystal X-ray diffraction. The investigated compound contains a new [HAs2Mo6O2...
The dimerization of a saturated N-heterocyclic carbene (NHC) to tricyclic piperazine in preference to commonly observed Wanzlick dimerization is presented. Mechanistic investigations revealed that the N-fluorene substituent of the heterocycle is implicated in both ring opening of corresponding carbene dimer and tautomerization of NHC to an azomethi...
N-(4-Bromobenzyl)-2-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)benzeneamine was obtained by condensation of N-(4-bromobenzyl)-3,1-benzoxazine-2,4-dione (N-(4-bromobenzyl)isatoic anhydride) with 4,5-dimethyl-1,2-phenylenediamine in refluxing acetic acid. This is a rare example of condensation of N-substituted 3,1-benzoxazine-2,4-dione with 1,2-phenylene...
A series of optically pure (R)- and (S)-1,3,4,12a-tetrahydropyrazino[2,1-c][1,4]benzodiazepine-6,12(2H,11H)-dione derivatives was designed and synthesized as novel anthramycin analogues in a three-step, one-pot procedure, and tested for their antiproliferative activity on nine following cell lines: MV-4-11, UMUC-3, MDA-MB-231, MCF7, LoVo, HT-29, A-...
A Sharpless asymmetric dihydroxylation reaction was applied to obtain ferrocenyl-GNA nucleosides. These are the first known representatives of redox active organometallic GNA ever reported and contribute to the expanding of GNA family tree. The (S,R) and (R,S) absolute configuration of the chiral carbon atoms in the Fc-GNA nucleosides was assigned...
The synthesis of four cymantrene-5-fluorouracil derivatives (1–4) and two cymantrene-adenine derivatives (5 and 6) is reported. All of the compounds were characterized by spectroscopic methods and the crystal structure of two derivatives (1 and 6), together with the previously described cymantrene-adenine compound C was determined by X-ray crystall...
Fluorescent pyrene–linker–nucleobase (nucleobase = thymine, adenine) conjugates with carbonyl and hydroxy functionalities in the linker were synthesized and characterized. X-ray single-crystal structure analysis performed for the pyrene–C(O)CH2CH2–thymine (2) conjugate reveals dimers of molecules 2 stabilized by hydrogen bonds between the thymine m...
1H NMR spectra, refinement data, and spectra in HeLa cells.
Highly stereoselective conjugate β-borylation, using a new chiral NHC-based copper catalyst, has been achieved. The chiral NHC copper complex was prepared in gram scale and showed high enantioselectivity and activity (up to 10 000 turnovers at 100 ppm of catalyst loading). This method was employed in the synthesis of chiral β-borylated ester from s...
Two bis-hydrazone, H4La and H4Lb, have been synthesized from reaction of 5,5'-methylene-bis-salicylaldehyde with benzhydrazide and furan-2-carbohydrazide, respectively. New organotin(IV) complexes, (R2Sn)2L [L = La: R = Me (1), Ph (2); L = Lb: R = Me (3), Ph (4)] have been synthesized by reaction of dihydrazone ligands with R2SnCl2 (R = Me or Ph)....
Phenyl-1,4-dihydrobenzo[e][1,2,4]triazinyl radicals with the N(1) position substituted with naphth-2-yl (1b), naphth-1-yl (1c), pyren-1-yl (1d), anthracen-9-yl (1e), 2-trifluoromethylphenyl (1f), 3-trifluoromethylphenyl (1g), and 2-iodophenyl (1h) were characterized by using single-crystal X-ray diffraction, variable temperature magnetic susceptibi...
(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione was obtained in a three-step, one-pot synthesis, starting from optically pure (S)-2-piperazine carboxylic acid dihydrochloride. Selective acylation of the β-nitrogen atom followed by condensation with isatoic anhydride and cyclization with HATU/DIPE...
The objective of these studies was to synthesize and characterize new diols with an imidazoquinazoline ring. New diols were obtained in reactions of 2,6-bis-(ethoxycarbonylmethyl)-1-phenylimidazo[1,5-c]quinazoline-3,5-dione with excess of ethylene glycol or in reaction of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione with 2-M excess of ethylen...
An investigation of the impact of alkyl spacer length of the flexible ligands and influence of shape and coordination ability of the counterions has been done on a series of five silver(I)-bis(imidazole-2-thione) coordination polymers. The five compounds, namely, [Ag2L⁴(NO3)²]n, {[AgL⁴]2[CF3SO3]2}n, [Ag2 L⁶(CF3SO3)2]n, [Ag2 L⁶(NO3)- (ClO4)]n, and [...
The synthesis of 1,1′-bis(thymine)ferrocene nucleoside is reported. This nucleoside was obtained in a two-step synthetic methodology including a Michael addition reaction of 1,1′-bis(3-chloropropionyl)ferrocene with thymine to afford the bis(thymine) adduct in 44 % yield. In the second step, the two prochiral carbonyl functionalities in the Michael...
The synthesis of a family of N-heterocyclic copper carbene complexes bearing sulfur moiety using different copper(I) halides and convenient route procedures have been reported. The solid state structures of presented copper compounds were elucidated using X-Ray crystallography. Next, obtained complexes were examined in various catalytic transformat...
Two new neutral fac-[Re(CO)3(phen)L] compounds (1,2), with phen = 1,10-phenanthroline and L = O2C(CH2)5CH3 or O2C(CH2)4C≡CH, were synthetized in one-pot procedures from fac-[Re(CO)3(phen)Cl] and the corresponding carboxylic acids, and were fully characterized by IR and UV-Vis absorption spectroscopy, ¹H- and ¹³C-NMR, mass spectrometry and X-ray cry...
N-(α-d-Glucofuranurono-6,3-lactone)-p-nitroaniline and N-(methyl β-d-glucopyranuronate)-p-nitroaniline were obtained as crystalline solids. The single-crystal X-ray diffraction, NMR data and DFT calculations for N-(α-d-glucofuranurono-6,3-lactone)-p-nitroaniline indicate that this N-furanoside adopts a ³T2/³E-like conformation in the crystal lattic...
1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione reacts with ethyl bromoacetate under mild conditions to give 2-(ethoxycarbonylmethyl)-1-phenyl-6H-imidazo[1,5-c]quinazoline-3,5-dione (MEPIQ) and next 2,6-bis(ethoxycarbonylmethyl)-1-phenylimidazo[1,5-c]quinazoline-3,5-dione (BEPIQ). The products were isolated at high yield and identified on the ba...
Synthesis of new derivatives with an imidazo[1,5-c]quinazoline-3,5-dione ring has been presented. Two new alcohols with the imidazo[1,5-c]quinazoline-3,5-dione ring were obtained and characterized by spectral (1H, 13C NMR, IR and UV) and crystallography methods. A reaction chemoselectivity has been observed with a formation of monohydroxyalkyl deri...
The Z/E isomerisations of the synthesized benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino-D-hexopyranosides during the NMR measurement and during the Zemplén O-deacetylation were observed. In order to study stabilities and tendency of the obtained compounds to isomerise, B3LYP/6-311++G∗∗ level geometry optimisations for four stereoisomers of methy...