New chalcone-type compounds and 2-pyrazoline derivatives: synthesis and caspase-dependent anticancer activity.

There is a continuous and urgent need for new anticancer agents with novel structures and target selectivity. The anticancer activity of the prepared compounds was assessed against human lung (A549) and stomach (AGS) cancer cell lines and evaluated in the noncancer human lung fibroblast (MRC-5) cell line. 2-Pyrazolines were devoid of toxicity in all cell lines used, chalcones bearing a β-(benz)imidazole moiety being toxic toward AGS cell line.

New (benz)imidazolopyridino tacrines as nonhepatotoxic, cholinesterase inhibitors for Alzheimer disease.

Aim: Due to the multifactorial nature of Alzheimer's disease, there is an urgent search for new more efficient, multitarget-directed drugs.

Results: This paper describes the synthesis, antioxidant and in vitro biological evaluation of ten (benz)imidazopyridino tacrines (7-16), showing less toxicity than tacrine at high doses, and potent cholinesterase inhibitory capacity, in the low micromolar range. Among them, compound 10 is a nonhepatotoxic tacrine at 1000 mM, showing moderate, but totally selective electric eel acetylcholinesterase inhibition, whereas molecule 16 is twofold less toxic than tacrine at 1000 μM, showing moderate and almost equipotent inhibition for electric eel acetylcholinesterase and equine butyrylcholinesterase.

Potent anticholinesterasic and neuroprotective pyranotacrines as inhibitors of beta-amyloid aggregation, oxidative stress and tau-phosphorylation for Alzheimer's disease.

Herein we describe the synthesis and in vitro biological evaluation of thirteen new, racemic, diversely functionalized 2-chloroquinolin-3-yl substituted PyranoTacrines (PTs) as multipotent tacrine analogues for Alzheimer's disease (AD) therapy. Among these compounds, 1-(5-amino-4-(2-chloro-7-methoxyquinolin-3-yl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrano [2,3-b]quinolin-3-yl)éthanone (9) and ethyl 5-amino-4-(2-chloroquinolin-3-yl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrano[2,3-b]quinoline-3-carboxylate (4) were found to be non-neurotoxic agents in human neuroblastoma SHSY5Y cells. Compounds 9 (IC50 = 0.

Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer's Disease Therapy.

Herein we describe the synthesis and in vitro biological evaluation of thirteen new, racemic, diversely functionalized imidazo pyranotacrines as non-hepatotoxic, multipotent tacrine analogues. Among these compounds, 1-(5-amino-2-methyl-4-(1-methyl-1H-imidazol-2-yl)-6,7,8,9-tetrahydro-4H-pyrano[2,3-b]quinolin-3-yl)ethan-1-one (4) is non-hepatotoxic (cell viability assay on HepG2 cells), a selective but moderately potent EeAChE inhibitor (IC50 = 38.7 ± 1.

Crystal structure of catena-poly[1,3-di-benzyl-benzimidazolium [[chlorido-mercurate(II)]-di-μ-chlorido]].

The asymmetric unit of the polymeric title compound, {(C21H19N2)[HgCl3]} n , comprises one-half of the cationic mol-ecule, the other half being generated by application of twofold rotation symmetry, one Hg and two Cl atoms. The Hg(II) atom, lying on a twofold rotation axis, exhibits a distorted triangular coordination environment and is surrounded by three Cl atoms with Hg-Cl distances in the range 2.359 (2)-2.

Crystal structure of {bis-[(1H-benzimid-azol-2-yl-κN (3))meth-yl]sulfane}dichloridomercury(II).

In the asymmetric unit of the title compound, [HgCl2(C16H14N4S)], the Hg(II) cation is linked to two Cl atoms and two imidazole N atoms of the chelating bis-[(1H-benzimidazol-2-yl)meth-yl]sulfane ligand, forming a slightly distorted tetra-hedral environment. The substitued imidazole rings of the ligand are almost perfectly planar [with maximum deviations of 0.017 (3) and 0.

Crystal structure of 1-[(1-methyl-5-nitro-1H-imidazol-2-yl)meth-yl]pyridinium iodide.

In the title salt, C10H11N4O2 (+)·I(-), the asymmetric unit consists of a pyridinium cation bearning a (1-methyl-5-nitro-1H-imidazol-2-yl)methyl group at the N position and an iodide anion. The imidazole ring is quasiplanar, with a maxiumum deviation of 0.0032 (16) Å, and forms a dihedral angle of 67.

Crystal structure of (E)-1-methyl-2-[2-(2-methoxphen-yl)ethen-yl]-4-nitro-1H-imidazole.

In the asymmetric unit of the title compound, C13H13N3O3, the 2-(2-methoxphen-yl)ethenyl unit is connected to the methyl-nitro-imidazole 1-methyl-4-nitro-1H-imidazole moiety. The mol-ecule is quasi-planar and the planes of the two rings form a dihedral angle of 0.92 (11)°.

Crystal structure of ethyl 2-chloro-5,8-di-meth-oxy-quinoline-3-carboxyl-ate.

In the title compound, C14H14ClNO4, the dihedral angle between the quinoline ring system (r.m.s.

Crystal structure of 1-methyl-2-[(E)-2-(4-methyl-phen-yl)ethen-yl]-4-nitro-1H-imidazole.

In the title mol-ecule, C13H13N3O2, the planes of the benzene and imidazole rings form a dihedral angle of 7.72 (5)°. In the crystal, mol-ecules are linked by weak C-H⋯N and C-H⋯O hydrogen bonds, forming layers parallel to (100).

Crystal structure of ethyl 2-chloro-6-methyl-quinoline-3-carboxyl-ate.

In the title compound, C13H12ClNO2, the dihedral angle between the planes of the quinoline ring system (r.m.s.

3-Anilino-5,5-di-methyl-cyclo-hex-2-enone.

In the title mol-ecule, C14H17NO, the 5,5-di-methyl-cyclo-hex-2-enone moiety is attached to an aniline group, the dihedral angle subtended [54.43 (3)°] indicating a significant twist. The hexaneone ring has a half-chair conformation with the C atom bearing two methyl groups lying 0.

2-p-Tolyl-2,3-di-hydro-quinolin-4(1H)-one.

In the title mol-ecule, C16H15NO, the tetra-hydro-pyridine ring is in a sofa conformation with the methine C atom forming the flap. The dihedral angle between the benzene rings is 80.85 (8)°.

2-(4-Chloro-phen-yl)-2,3-di-hydro-quinolin-4(1H)-one.

The title mol-ecule, C15H12ClNO, features a di-hydro-quinolin-4(1H)-one moiety attached to a chloro-benzene ring. The heterocyclic ring has a half-chair conformation with the methine C atom lying 0.574 (3) Å above the plane of the five remaining atoms (r.

7-Meth-oxy-2-phenyl-quinoline-3-carbaldehyde.

In the title mol-ecule, C17H13NO2, the phenyl ring is inclined to the quinoline ring system by 43.53 (4)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming double-stranded chains propagating along [011].

2-Hy-droxy-methyl-1,3-dimethyl-1H-benzimidazol-3-ium iodide.

In the cation of the title compound, C10H13N2O(+)·I(-), all non-H atoms, with the exception of the O atom, are essentially coplanar, with a maximum deviation of 0.04 (1) Å. In the crystal, the cations and anions are arranged in layers parallel to (100).

2-Hy-droxy-methyl-1,3-dimethyl-1H-imidazol-3-ium triiodide.

The crystal packing of the title salt, C6H11N2O(+)·I3 (-), can be described as consisting of alternating layers of cations and anions parallel to the (100) plane along the a-axis direction. The components are linked by O-H⋯I, C-H⋯I and C-H⋯O interactions, generating a three-dimensional network. The O atom deviates from the imidazol ring by 0.

Methyl 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetate.

In the crystal of the title compound, C7H9N3O4, mol-ecules are linked by weak C-H⋯O hydrogen bonds into chains along the a-axis direction. The dihedral angle between the ring and the nitro group is 3.03 (6), while that between the ring and the acetate group is 85.

(2E,2'E)-1,1'-Bis(6-chloro-2-methyl-4-phenyl-quinolin-3-yl)-3,3'-(1,4-phenyl-ene)diprop-2-en-1-one ethyl acetate disolvate.

In the title solvate, C44H30Cl2N2O2·2C4H8O2, the complete polycyclic mol-ecule is generated by inversion symmetry. The dihedral angle between the quinolyl ring system (Q; r.m.

Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus.

Several new highly functionalized imidazolium derivatives were synthesized, via appropriate synthetic routes, using imidazole, 1-methylimidazole and 2-phenyl-1-methylimidazole as key intermediates. The antibacterial activity of the prepared compounds was evaluated against: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella thipymurium using disk-diffusion and MIC methods. Crystal X-ray structures are reported for six compounds.

3-(1H-1,3-Benzimidazol-2-yl)-2,7-dimeth-oxy-quinoline.

In the title mol-ecule, C(18)H(15)N(3)O(2), the dihedral angle between the quinoline and benzimidazole ring systems is 23.57 (5)°. The C atoms of the meth-oxy groups are both close to being coplanar with their attached ring systems [deviations = 0.

rac-2-(2-Chloro-6-methyl-quinolin-3-yl)-2,3-dihydro-quinolin-4(1H)-one.

In the title compound, C(19)H(15)ClN(2)O, the quinoline ring forms a dihedral angle of 43.24 (1)° with the benzene ring of the dihydroquinolinyl system. In the crystal, mol-ecules are linked through a single weak C-H⋯O hydrogen bond, forming ribbons which extend along (100), giving alternating zigzag mol-ecular layers which stack down the b-axis direction.

2-Chloro-3-[(E)-(hydrazin-1-yl-idene)meth-yl]-6-meth-oxy-quinoline.

In the title compound, C(11)H(10)ClN(3)O, the quinoline ring system is essentially planar, the r.m.s.

4,5-Dibromo-1,2-dimethyl-1H-imidazol-3-ium bromide.

In the title salt, C(5)H(7)Br(2)N(2) (+)·Br(-), the cation and anion are connected by an N-H⋯Br hydrogen bond. In the crystal, there are inter-calated layers parallel to (10-2) in which bromide ions are located between the cations. Weak inter-molecular C-H⋯Br hydrogen bonds are also observed.

2-(2-Chloro-6,7-dimethyl-quinolin-3-yl)-2,3-dihydro-quinolin-4(1H)-one.

In the title mol-ecule, C(20)H(17)ClN(2)O, the dihedral angle between the mean plane of the quinoline ring system and the benzene ring of the dihydro-quinolinone moiety is 57.84 (8)°. In the crystal, mol-ecules are linked into centrosymmetric dimers via pairs of inter-molecular N-H⋯N hydrogen bonds.