Synthesis and Structure of 5-Methyl-9-(trifluoromethyl)-12-quino[3,4-][1,4]benzothiazinium Chloride as Anticancer Agent.

In this work, the synthesis, structural analysis and anticancer properties of 5-methyl-9-trifluoromethyl-12-quino[3,4-][1,4]benzothiazinium chloride () are described. Compound was synthesized by reacting 1-methyl-4-butylthio-3-(benzoylthio)quinolinium chloride with 4-(trifluoromethyl)aniline, respectively. The structure of the resulting product was determined using H-NMR and C-NMR spectroscopy as well as HR-MS spectrometry.

A New Structural Motif in Aggregation of Methylalumoxanes: Non-Hydrolytic Route by the Alkylation of Dicarboxylic Acids.

Alumoxanes are typically produced via controlled hydrolysis of short-chain alkyl aluminium compounds which leads to oligomeric species that are usually difficult to obtain in crystalline form. Simultaneously, various alternative non-hydrolytic approaches to alumoxanes have also been used. In this work, we report on a new methylalumoxane scaffold derived from the alkylation of a series of dicarboxylic acids: itaconic acid (HOCCHC(=CH)COH), succinic acid (HOCCHCHCOH) and homophthalic acid (HOCCHCHCOH).

2,3-Dichloroanthracene crystal, a new rigid matrix for single molecule optical investigations.

Absorption and emission spectra of single crystals of 2,3-dichloroathracene (23DCA) and 23DCA dispersed in n-nonane matrix were studied at 5 K. Singlet and triplet excitonic bands in the crystal were estimated to be at about 415 nm and at wavelengths shorter than 700 nm, respectively. Thus, from the spectroscopic point of view, these crystals satisfy all criteria for a transparent and rigid matrix for low temperature optical studies of single molecules of dibenzoterrylene, which have their purely electronic S→S transition at around 785 nm.

Towards Anticancer and Antibacterial Agents: Design and Synthesis of 1,2,3-Triazol-quinobenzothiazine Derivatives.

In this paper, we describe a new method for synthesizing hybrid combinations of 1,2,3-triazoles with a tetracyclic quinobenzothiazinium system. The developed approach allowed for the production of a series of new azaphenothiazine derivatives with the 1,2,3-triazole system in different positions of the benzene ring. In practice, the methodology consists of the reaction of triazole aniline derivatives with thioquinanthrenediinium -chloride.

Design, Synthesis and Antimicrobial Properties of New Tetracyclic Quinobenzothiazine Derivatives.

A new method for modifying the structure of tetracyclic quinobenzothiazinium derivatives has been developed, allowing introduction of various substituents at different positions of the benzene ring. The method consists of reacting appropriate aniline derivatives with 5,12-(dimethyl)thioquinantrenediinium bis-chloride. A series of new quinobenzothiazine derivatives was obtained with propyl, allyl, propargyl and benzyl substituents in 9, 10 and 11 positions, respectively.

Towards Property Profiling: SYNTHESIS and SAR Probing of New Tetracyclic Diazaphenothiazine Analogues.

A series of new tertiary phenothiazine derivatives containing a quinoline and a pyridine fragment was synthesized by the reaction of 1-methyl-3-benzoylthio-4-butylthioquinolinium chloride with 3-aminopyridine derivatives bearing various substituents on the pyridine ring. The direction and mechanism of the cyclization reaction of intermediates with the structure of 1-methyl-4-(3-pyridyl)aminoquinolinium-3-thiolate was related to the substituents in the 2- and 4-pyridine position. The structures of the compounds were analyzed using H, C NMR (COSY, HSQC, HMBC) and X-ray analysis, respectively.

Photophysical transformations induced by chemical substitution to salicylaldimines.

A series of different electron-deficient aromatic substituents were used to investigate the role of the electron-acceptor strength on the photophysical properties of salicylaldimine derivatives. These molecules were synthesised and characterised through X-ray diffraction, absorption and emission spectroscopies. Their photochemical reaction mechanisms and properties were explored with the aid of ab initio methods of quantum chemistry.

Heteroleptic [Os(Cl)(CO)(P^P)(pbi)] complexes bearing bidentate phosphine and 2-(2-pyridyl)benzimidazolate ligands: impact of isomerism on their luminescence properties.

A series of six [Os(Cl)(CO)(P^P)(pbi)] complexes have been synthesized and characterized using FT-IR, 1H NMR, and 31P NMR spectroscopy. Their molecular structures have been confirmed by means of X-ray diffraction studies. For each of the studied bidentate phosphines (P^P = cis-1,2-bis(diphenylphosphino)ethene - dppv, 1,2-bis(diphenylphosphino)ethane - dppe, 1,2-bis(diphenylphosphino)benzene - dppb) the applied synthesis procedure has afforded preparation of two isomers with pseudo-octahedral coordination of the osmium(ii) ion.

Electron transfer across a spiro link: extreme solvatofluorochromism of a compact spiro-bridged N,N-dimethylaniline-phthalide dyad.

Intramolecular electron transfer over the sp-C-link in dimethyl-aniline-spiro-phthalide leads to extreme solvatofluorochromism (11 600 cm) and a fluorescence maximum shift from 357 (hexane) to 595 nm (acetonitrile). The spiro link enhances π-σ* negative hyperconjugation leading to C-O bond elongation and electron transfer over a longer distance than in a non-spirocyclic analogue.

Evaluation of angularly condensed diquinothiazines as potential anticancer agents.

We present efficient synthesis of isomeric types of angularly fused diquinothiazines in the reactions of 2,2'-dichloro-3,3'-diquinolinyl disulfide and diquinodithiin with 3-, 5-, 6- and 8-aminoquinolines. The pentacyclic diquinothiazine ring systems were identified as diquino[3,2-b;3',4'-e][1,4]thiazine, diquino[3,2-b;5',6'-e][1,4]thiazine, diquino[3,2-b;6',5'-e][1,4]thiazine and diquino[3,2-b;8',7'-e][1,4]thiazine with advanced two-dimensional H and C NMR techniques (COSY, ROESY, HSQC and HMBC) of N-methyl derivatives. The identification of pentacyclic ring system was confirmed by X-ray diffraction analysis of selected N-alkyl derivatives.

Heteroleptic [Os(H)(CO)(NN)(tpp)] and [Os(Cl)(CO)(NN)(tpp)] complexes - comparative studies of their luminescence properties.

Two series of cationic heteroleptic osmium(ii) complexes with a coordinated CO molecule, a chloride Cl or hydride H anion, two monodentate triphenylphosphine (tpp) ligands and one bidentate α-dimine (NN) ligand were prepared from an OsCl(CO)(tpp) precursor. The investigated complexes, available in the form of PF salts, have been identified by means of FT-IR, H and P NMR spectroscopy and X-ray diffraction studies. Their photophysical properties have been investigated in dichloromethane solutions at room temperature and 1 : 1 ethanol-methanol matrices at 77 K.

3,6-Diazaphenothiazines as potential lead molecules - synthesis, characterization and anticancer activity.

3,6-Diazaphenothiazines were obtained in cyclization of 3-amino-3'-nitro-2,4'-dipyridinyl sulfide and the reaction of sodium 3-amino-2-pyridinethiolate with 4-chloro-3-nitropyridine followed by alkylation and heteroarylation. The thiazine ring formation ran via the Smiles rearrangement. The structure elucidation was based on 2D NMR and X-ray analysis of N-methylated product.

Novel imidazolium and imidazolinium salts containing the 9-nickelafluorenyl anion--synthesis, structures and reactivity.

Investigation of the properties of carbene complexes is one of the most important fields of modern coordination chemistry. In this paper, we propose the convenient synthesis of NHC-nickel compounds. The 9-nickelafluorenyllithium complex reacts with imidazolium or imidazolinium salts to afford 9-nickelafluorenyl-NHC salts via ionic metathesis with very good yields (66-92%).

β-Cyclodextrin as the suitable molecular container for isopulegol enantiomers.

Isopulegol, an insoluble in water and highly volatile compound, due to its neuroactive properties is a potentially important agent for medical applications. Formation of "host-guest" molecular complexes with cyclodextrins would lead to the increase of its water solubility and bioavailability. Interactions between native cyclodextrins (α, β and γ) and isopulegol enantiomers were studied in solution proving the formation of inclusion complexes for β- and γ-cyclodextrins.

6-[3-(p-Tolyl-sulfonyl-amino)-prop-yl]diquino-thia-zine.

In the title mol-ecule {systematic name: N-[3-(diquino[3,2-b;2',3'-e][1,4]thia-zin-6-yl)prop-yl]-4-methyl-benzene-sulfon-amide}, C28H24N4O2S2, the penta-cyclic system is relatively planar [maximum deviation from the mean plane = 0.242 (1) Å]. The dihedral angle between two quinoline ring systems is 8.

N-[4-(9-Chloro-quino[3,2-b]benzo[1,4]thia-zin-6-yl)but-yl]acetamide.

In the title mol-ecule, C21H20ClN3OS, the tetra-cyclic system is close to planar [r.m.s.

10-(Prop-2-yn-1-yl)-2,7-diaza-phenothia-zine.

In the title mol-ecule [systematic name: 10-(prop-2-yn-1-yl)dipyrido[3,4-b:3',4'-e][1,4]thia-zine], C(13)H(9)N(3)S, the dihedral angle between the two pyridine rings is 146.33 (7)° and the angle between two halves of the thia-zine ring is 138.84 (8)°, resulting in a butterfly shape for the tricyclic system.

Transformations of griseofulvin in strong acidic conditions--crystal structures of 2'-demethylgriseofulvin and dimerized griseofulvin.

The structure of griseofulvic acid, C16H15ClO6, at 100 K has orthorhombic (P2(1)2(1)2) symmetry. It is of interest with respect to biological activity. The structure displays intermolecular O-H.

Monolayers of an amphiphilic para-carboxy-calix[4]arene act as templates for the crystallization of acetaminophen.

The title compound, 5,11,17,23-tetra-carboxy-25,26,27,28-tetradodecyloxy-calix[4]arene, 1, has been studied at the air-water interface, self-assembled as Langmuir monolayers, for its ability to interact with an active pharmaceutical ingredient (API), acetaminophen (APAP), and to initiate its crystallization. The Π/A isotherm study shows that there is a clear interaction between 1 and APAP causing an expansion of the monolayer. In addition to the known phase transition occurring at a surface tension of 38 mN m(-1), an additional kink is observed in the compression isotherm for concentrations of APAP above 40 mM suggesting that this API is causing an additional phase transition of the monolayer.

Amidophenol-modified amphiphilic calixarenes: synthesis, interfacial self-assembly, and acetaminophen crystal nucleation properties.

Three amidophenol-modified calixarenes have been produced reacting the parent 5,11,17,23-tetracarboxy-25,26,27,28-tetradodecyloxycalix[4]arene with o-, m-, and p-aminophenol. The produced amphiphiles have been shown to form stable monomolecular Langmuir layers on water. Working on subphases containing 1 mM acetaminophen (APAP), it has been demonstrated that the produced amphiphiles interact with this active pharmaceutically ingredient (API) with a relevant preference for the para-derivative that possesses in its structure substituents that are analogous to the target.

A dodecameric self-assembled calix[4]arene aggregate with two types of cavities.

Twelve molecules of β-carbonyl-para-octyl-calix[4]arene assemble in an aggregate containing two types of cavities filled by water molecules and they pack in a cubic structure. Both the aggregates and the packing resemble that observed for inverse micelles.

Cyclo[2]benzimidazole: luminescence turn-on sensing of anions.

Cyclo[2]benzimidazole is a new host for anions that turns on its luminescence up to 150 fold upon binding. Photoexcited cyclo[2]benzimidazole undergoes an efficient non-radiative deactivation through an excited-state intramolecular proton-transfer (ESIPT) mechanism. Upon binding an anion, the ESIPT pathway is blocked, resulting in an increase in the luminescence efficiency.

Solid-state interactions of calixarenes with biorelevant molecules.

Among all crystalline complexes of calix-type calix[n]arenes those with organic molecules which are biologically relevant are especially of interest due to their potential medical and pharmaceutical applications. The co-crystallization of drugs with water-soluble calixarenes offers the opportunity to modify chemical and physical properties of APIs (active pharmaceutical ingredients) and to control drug conformation. Such co-crystallization can improve solubility, bioavailability and stability of pharmaceutically active molecules and/or eliminate polymorphism.

Streptidinium sulfate monohydrate.

In streptidinium sulfate monohydrate {systematic name: 1,1'-[(1S,3R,4S,6R)-2,4,5,6-tetrahydroxycyclohexane-1,3-diyl]diguanidinium sulfate monohydrate}, C(8)H(20)N(6)O(4)(2+).SO(4)(2-).H(2)O, at 100 (2) K, the components are arranged in double helices based on hydrogen bonds.