Sema Öztürk Yildirim

Microwave-assisted synthesis and myorelaxant activity of 9-indolyl- 1,8-acridinedione derivatives

In this study a microwave-assisted method was applied for the synthesis of novel 9-(substituted indolyl)-3,4,6,7-tetrahydroacridine-1,8-(2H,5H,9H,10H)-dione derivatives. The structures of the compounds were confirmed by spectral methods including X-ray studies and elemental analysis. The Emax and pD2 values of the compounds and pinacidil were determined on noradrenaline precontracted tissues of isolated strips of rabbit gastric fundus smooth muscle. The obtained results indicated that some compounds and pinacidil produced concentration-dependent relaxation on the strips. The efficacy of compound 9 was higher than pinacidil. Docking studies were carried out to understand the interactions of the compounds with the active site of potassium channel. Methyl substituents on the acridine backbone and bromine atom on the indole ring led to more active compounds.

3,3,6,6-Tetra­methyl-9-(1-methyl-1H-indol-2-yl)-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione

In the acridine system of the title molecule, C26H30N2O2, both cyclohex-2-enone rings adopt sofa conformations. The indole ring system is essentially planar, with a maximum deviation of 0.017u2005(2)u2005Å for a bridgehead C atom. An intramolecular C—H⋯O hydrogen bond occurs. The molecules assemble into C(6) chains in the crystal by way of N—H⋯O hydrogen bonds.

Ethyl 4-(5-bromo-1H-indol-3-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate

The title compound, C23H25BrN2O3, crystallizes with two independent molecules in the asymmetric unit (Z′ = 2) which differ in the twist of the 5-bromo-1H-indole ring with respect to the plane of the 4-methyl-1,4,5,6,7,8-hexahydroquinoline ring [dihedral angles of 78.55u2005(9) and 89.70u2005(8)° in molecules A and B, respectively]. The indole ring is planar in both molecules [maximum deviations = 0.021u2005(3) and −0.020u2005(3)u2005Å for the N atom] while the cyclohexene ring has adopts a sofa conformation. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming dimers with R 1 2(6) ring motifs. These dimers are connected by N—H⋯O hydrogen bonds, generating chains along [110]. A C—H⋯O contact occurs between the independent molecules.

Experimental and computational study on 2,2'-[(1E,2E)-hydrazine-1,2-diylidenedi(1E)eth-1-yl-1-ylidene]diphenol and its Ni(II), Pt(II), Pd(II) complexes.

2,2-[(1E,2E)-hydrazine-1,2-diylidenedi(1E)eth-1-yl-1-ylidene]diphenol and its dimeric, binuclear Ni(II), Pd(II) and Pt(II) metal complexes were synthesized. Hydrazine derivative and its complexes were characterized by elemental analyses, LC-MS, IR, electronic spectra, (1)H and (13)C NMR spectra, conductivity and magnetic measurements. 1H and 13C shielding tensors for crystal structure were calculated with GIAO/DFT/B3LYP/6-311++G(d,p) methods in CDCl3. The vibrational band assignments were performed at B3LYP/6-311++G(d,p) theory level combined with scaled quantum mechanics force field (SQMFF) methodology. The antibacterial activities of synthesized compounds were studied against some Gram-positive and Gram-negative bacteria by using the microdilution and disk diffusion method. As the antibacterial activity results evidently show, the compound possessed a broad spectrum of activity against the tested bacteria.

2-(1-Phenyl-1H-benzimidazol-2-yl)phenol

In the title molecule, C19H14N2O, the benzimidazole unit is close to being planar [maximum deviation = 0.0253u2005(11)u2005Å] and forms dihedral angles of 68.98u2005(6) and 20.38u2005(7)° with the adjacent phenyl and benzene rings; the dihedral angle between the latter two planes is 64.30u2005(7)°. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by C—H⋯N and C—H⋯O hydrogen bonds, and consolidated into a three-dimensional architecture by π–π stacking interactions, with a centroid–centroid distance of 3.8428u2005(12)u2005Å.

Ethyl 2,7,7-trimethyl-4-(1-methyl-1H-indol-3-yl)-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate

In the title molecule, C24H28N2O3, the cyclohexene ring is in a sofa conformation and the 1,4-dihydropyridine ring is in a slight boat conformation. In the indole ring system, the pyrrole and benzene rings form a dihedral angle of 2.63u2005(7)°. In the crystal, N—H⋯O hydrogen bonds connect the molecules into C(6) chains parallel to the b axis and pairs of weak C—H⋯O hydrogen bonds link inversion-related chains into a ladder motif through R 2 2(18) rings. A weak intramolecular C—H⋯O hydrogen bond is also observed.

N,N-Dicyclo­hexyl-4-nitro­benzamide

The title compound, C19H26N2O3, crystallizes with two independent molecules in the asymmetric unit which differ in the twist of the phenyl rings with respect to the plane of the amide group [the C—C—C—O torsion angles are 121.5u2005(3) and −119.6u2005(3)° in the two molecules. Both cyclohexane rings adopt chair conformations. In the crystal, weak C—H⋯O interactions occur. The crystal studied was a non-merohedral twin with a minor component of 4.8u2005(1)%.

1,2-Diphenyl-1H-benzimidazole

In the title molecule, C19H14N2, the benzimidazole unit is close to being planar [maximum deviation = 0.0102u2005(6)u2005Å] and forms dihedral angles of 55.80u2005(2) and 40.67u2005(3)° with the adjacent phenyl rings; the dihedral angle between the phenyl rings is 62.37u2005(3)°. In the crystal, one C—H⋯N hydrogen bond and three weak C—H⋯π interactions involving the fused benzene ring and the imidazole ring are observed, leading to a three-dimensional architecture.

1,1,2,2-Tetra-kis[2,4-dichloro-6-(dieth-oxy-meth-yl)phen-oxy-meth-yl]ethene.

In the title compound, C50H60Cl8O12, the molecules are disordered about an inversion center located at the mid-point of the central C=C bond. These atoms show disorder and were modelled with two different orientations with site occupancies of 0.828u2005(3) and 0.172u2005(3). The dihedral angle between the two benzene rings in the asymmetric unit is 52.80u2005(6)°. Intramolecular C—H⋯O and C—H⋯Cl interactions occur and the crystal packing features inversion dimers linked by pairs of C—H⋯O bonds, generating R 2 2(10) loops.

Ethyl 2-[2-(4-hy­droxy-3-meth­oxy­benzyl­idene)hydrazin-1-yl­idene]-3,4-dimethyl-2,3-dihydro-1,3-thia­zole-5-carboxyl­ate

The title compound, C16H19N3O4S, is almost planar, with a dihedral angle of 2.88u2005(9)° between the mean planes of the benzene and thiazole rings. The molecule adopts an E conformation about the two C=N bonds, with a C—N—N—C torsion angle of −177.01u2005(11)°. An intramolecular C—H⋯O hydrogen bond exists between a thiazole methyl group and the formic acid ethyl ester carbonyl O atom. In the crystal, molecules are linked by O—-H⋯O hydrogen bonds, forming chains propagating along [2-10]. The chains are linked via C—H⋯O hydrogen bonds with R 2 2(12) ring motifs, forming sheets lying parallel to (12-2). The sheets are further linked through out-of-plane C—H⋯N hydrogen bonds with R 2 2(12) ring motifs and C—H⋯π interactions, forming an interesting three-dimensional supramolecular architecture.