9-(4-Fluoro­phen­oxy­carbon­yl)-10-methyl­acridinium trifluoro­methane­sulfonate

In the crystal structure of the title compound, C21H15FNO2 +·CF3SO3 −, the cations form inversion dimers through C—H⋯O, C—F⋯π and π–π inter­actions. These dimers are further linked by π–π inter­actions. The cations and anions are connected through C—H⋯O, C—F⋯π and S—O⋯π inter­actions. The acridine and benzene ring systems are oriented at a dihedral angle of 74.1 (1)°. The carboxyl­ate group is twisted at an angle of 4.4 (1)° relative to the acridine skeleton. The mean planes of the adjacent acridine moieties are parallel or inclined at an angle of 55.4 (1)° in the crystal structure

10-Methyl-9-[2-(propan-2-yl)phenoxy­carbonyl]­acridinium trifluoro­methane­sulfonate

In the crystal of the title compound, C24H22NO2 +·CF3SO3 −, adjacent cations and anions are connected through C—H⋯O, C—H⋯F and S–O⋯π inter­actions, while neighboring cations via π–π inter­actions [centroid–centroid distance = 3.962 (2) Å]. The acridine and benzene ring systems are oriented at a dihedral angle of 14.6 (1)°. The carboxyl group is twisted at an angle of 87.6 (1)° relative to the acridine skeleton. The mean planes of adjacent acridine units are parallel or inclined at an angle of 13.4 (1)° in the crystal structure

9-(3-Fluoro­phen­oxy­carbon­yl)-10-methyl­acridinium trifluoro­methane­sulfonate monohydrate

In the crystal structure of the title mol­ecular salt, C21H15FNO2 +·CF3SO3 −·H2O, the cations form inversion dimers through π–π inter­actions between the acridine ring systems. These dimers are linked via C—H⋯O and C—F⋯π inter­actions to adjacent anions, and by C—H⋯π and C—F⋯π inter­actions to neighbouring cations. The water mol­ecule links two sites of the cation by C—H⋯O inter­actions and two adjacent anions by O—H⋯O hydrogen bonds. The mean planes of the acridine and benzene ring systems are oriented at a dihedral angle of 15.1 (1)°. The carboxyl group is twisted at an angle of 84.5 (1)° relative to the acridine skeleton. The mean planes of the acridine ring systems are parallel in the crystal

Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design

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-alkyl-, N-acetyl- and dithio analogues. Developed procedures allowed the synthesis of unsymmetrical dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones and three novel heterocyclic scaffolds: benzo[b]naphtho[2,3-f][1,5]diazocine-6,14(5H,13H)dione, pyrido[3,2-c][1,5]benzodiazocine-5,11(6H,12H)-dione and pyrazino[3,2-c][1,5]benzodiazocine-6,12(5H,11H)dione. For 11 of the compounds crystal structures were obtained. The preliminary cytotoxic effect against two cancer (HeLa, U87) and two normal lines (HEK293, EUFA30) as well as antibacterial activity were determined. The obtained dibenzo[b,f][1,5]diazocine(5H,11H)6,12-dione framework could serve as a privileged structure for the drug design and development

10-Methyl-9-phenoxy­carbonyl­acridinium trifluoro­methane­sulfonate monohydrate

In the crystal structure of the title compound, C21H16NO2 +·CF3SO3 −·H2O, the anions and the water mol­ecules are linked by O—H⋯O inter­actions, while the cations form inversion dimers through π–π inter­actions between acridine ring systems. These dimers are linked by C—H⋯O and C—F⋯π inter­actions to adjacent anions, and by C—H⋯π inter­actions to neighboring cations. The water mol­ecule links two H atoms of the cation by C—H⋯O inter­actions and two adjacent anions by O—H⋯O inter­actions. The acridine and benzene ring systems are oriented at 15.6 (1)°. The carboxyl group is twisted at an angle of 77.0 (1)° relative to the acridine skeleton. The mean planes of the adjacent acridine units are either parallel or inclined at an angle of 18.4 (1)°

9-(2-Bromo­phen­oxy­carbon­yl)-10-methyl­acridinium trifluoro­methane­sulfonate

In the crystal structure of the title compound, C21H15BrNO2 +·CF3SO3 −, adjacent cations are linked through C—Br⋯π and π–π contacts [centroid–centroid distance = 3.744 (2) Å], and neighbouring cations and anions via C—H⋯O, C—F⋯π and S—O⋯π inter­actions. The acridine and benzene ring systems are oriented at a dihedral angle of 18.7 (1)°. The carb­oxy group is twisted at an angle of 69.3 (1)° relative to the acridine skeleton. The mean planes of adjacent acridine moieties are either parallel or inclined at an angle of 27.8 (1)° in the lattice

9-(4-Methyl­phenoxy­carbon­yl)-10-methyl­acridinium trifluoro­methane­sulfonate

In the crystal structure of the title compound, C22H18NO2 +·CF3SO3 −, adjacent cations are linked through C—H⋯π and π–π inter­actions, and the cations and anions are connected by C—H⋯O and C—F⋯π inter­actions. The acridine and benzene ring systems are oriented at a dihedral angle of 3.0 (1)°. The carboxyl group is twisted at an angle of 83.1 (1)° relative to the acridine skeleton. The mean planes of adjacent acridine units are parallel or inclined at an angle of 75.2 (1)° in the crystal structure

9-Phenyl-10H-acridinium trifluoro­methane­sulfonate

In the crystal structure of the title compound, C19H14N+·CF3SO3 −, the cations are linked to each other by very weak C—H⋯π inter­actions, while the cations and anions are connected by N—H⋯O, C—H⋯O and S—O⋯π inter­actions. The acridine ring system and the phenyl ring are oriented at an angle of 80.1 (1)° with respect to each other. The mean planes of adjacent acridine units are either parallel or inclined at an angle of 35.6 (1)°. The trifluoro­methane­sulfonate anions are disordered over two positions; the site occupancy factors are 0.591 (8) and 0.409 (8)

Unsymmetrically-Substituted 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione Scaffold—A Useful Tool for Bioactive Molecules Design

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, expanding the structural diversity and possible applications of synthesized molecules. The extension of developed method resulted in the synthesis of novel: tricyclic 5,10-dihydrobenzo[b]thieno[3,4-f][1,4]diazocine-4,11-dione scaffold and fused pentacyclic framework possessing two benzodiazocine rings within its structure. Additionally, the unprecedented rearrangement of 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-diones to 2-(2-aminophenyl)isoindoline-1,3-diones was observed under the basic conditions in the presence of sodium hydride for secondary dilactams. The structures of nine synthesized products have been established by single-crystal X-ray diffraction analysis. Detailed crystallographic analysis of the investigated tri- and pentacyclic systems has shed more light on their structural features. One cell line derived from non-cancerous cells (EUFA30—human fibroblasts) and three tumor cells (U87—human primary glioblastoma, HeLa—cervix adenocarcinoma, BICR18—laryngeal squamous cell carcinoma) were used to determine the cytotoxic effect of the newly synthesized compounds. Although these compounds showed a relatively weak cytotoxic effect, the framework obtained for 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione could serve as a convenient privilege structure for the design and development of novel bioactive molecules suitable for drug design, development and optimization programs

Esters with imidazo [1,5-c] quinazoline-3,5-dione ring spectral characterization and quantum-mechanical modeling

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 basis of IR, 1H- and 13C-NMR, UV spectroscopy, and X-ray crystallography. Diester (BEPIQ) can be presented by 16 possible pair of enantiomers. Only one pair of them is the most stable and crystallizes which is shown crystallographic research. Based on quantum-mechanical modeling, with the use of DFT method, which conformers of mono- and diester and why they were formed was explained. It was calculated that 99.93% of the monoester (MEPIQ) is formed at position No. 2 and one pair of the monoester conformers, from six possible, has the largest share (51.63%). These results afforded to limit the number of diester conformers to eight. Unfortunately, the quantum-mechanical calculations performed that their shares are similar. Further quantum-mechanical modeling showed that conformers are able to undergo mutual transformations. As a result only one pair of diester conformers forms crystals. These conformers have substituents in trans position and these substituents are located parallel to imidazoquinazoline ring. This allows for the denser packing of the molecules in the unit cell. © 2017, The Author(s).IGA/FT/2016/004, UTB, Univerzita Tomáše Bati ve ZlíněInterdisciplinary Centre for Mathematical and Computational Modelling in Warsaw [G49-12]; TBU in Zlin [IGA/FT/20017/005