Synthesis, Crystal Structure, DFT, and Anticancer Activity of Some Imine-Type Compounds via Routine Schiff Base Reaction: An Example of Unexpected Cyclization to Oxazine Derivative.

The synthesis, characterization, and anticancer properties of three imine-type compounds - and an unexpected oxazine derivative are presented. The reaction of -dimethylaminobenzaldehyde or -nitrobenzaldehyde with hydroxylamine hydrochloride afforded the corresponding oximes - in good yields. Additionally, the treatment of benzil with 4-aminoantipyrine or -aminophenol was investigated.

A New Pt(II) Complex with Anionic -Triazine Based -Donor Ligand: Synthesis, X-ray Structure, Hirshfeld Analysis and DFT Studies.

The reaction of PtCl with -triazine-type ligand () (1:1) in acetone under heating afforded a new complex. Single-crystal X-ray diffraction analysis showed that the ligand () is an tridentate chelate via two N-atoms from the -triazine and hydrazone moieties and one oxygen from the deprotonated phenolic OH. The coordination environment of the Pt(II) is completed by one Cl ion to the Pt-N.

Alteration of Anticancer and Protein-Binding Properties of Gold(I) Alkynyl by Phenolic Schiff Bases Moieties.

A set of five gold complexes with the general formula Au(PR)(C≡C-CH-4-R') (R = PPh, R' = -CHO (1), R = PCy, R' = -CHO (2), R = PPh, R' = -N=CH-CH-2-OH (3), R = PPh, R' = -N=CH-CH-4-OH (4), R = PCy, R' = -N=CH-CH-2-OH (5)) were synthesized and characterized by elemental analysis, H-NMR spectroscopy, P-NMR spectroscopy, and mass spectrometry. The structures of complexes 2 and 5 were determined by X-ray crystallography. The effects of the structural modifications on the protein binding affinities and anticancer activities of the five gold complexes were assessed.

Crystal structures of ()-1-naphthaldehyde oxime and ()-phenanthrene-9-carbaldehyde oxime.

The aldoximes CHNO (I) and CHNO (II), synthesized in 90% yield, by treatment of 1-naphthaldehyde or phenanthrene-9-carbaldehyde, respectively, with hydroxyl-amine hydro-chloride and sodium carbonate, have been characterized by IR, H, C and DEPT-135 NMR spectroscopies, and also by single-crystal X-ray diffraction analysis. The mol-ecules of (I) and (II) are conformationally similar, with the aldoxime substituent groups lying outside the planes of the naphthalene or phenanthrene rings, forming dihedral angles with them of 23.9 (4) and 27.

Crystal structure of -di-chloridobis-[-(5,5-di-methyl-4,5-di-hydro-3-pyrrol-2-yl-κ)acetamide]palladium(II) dihydrate.

The title complex, [PdCl(CHNO)]·2HO, was obtained by N-O bond cleavage of the oxa-diazo-line rings of the -[di-chlorido-bis-(2,5,5-trimethyl-5,6,7,7a-tetra-hydro-pyrrolo-[1,2-][1,2,4]oxa-diazole-)]palladium(II) complex. The palladium(II) atom exhibits an almost square-planar coordination provided by two -arranged chloride anions and a nitro-gen atom from each of the two neutral organic ligands. In the crystal, N-H⋯O, O-H⋯O and O-H⋯Cl hydrogen bonds link complex mol-ecules into double layers parallel to the plane.

A new thio-Schiff base fluorophore with copper ion sensing, DNA binding and nuclease activity.

Copper ion recognition and DNA interaction of a newly synthesized fluorescent Schiff base (HPyETSC) were investigated using UV-vis and fluorescent spectroscopy. Examination using these two techniques revealed that the detection of copper by HPyETSC is highly sensitive and selective, with a detection limit of 0.39 μm and the mode of interaction between HPyETSC and DNA is electrostatic, with a binding constant of 8.

Crystal structure of 4-methyl-N-[(4-methyl-pyridin-2-yl)carbamo-thioyl]-benzamide.

In the title compound, C15H15N3OS, the dihedral angle between the planes of the benzene and pyridine rings is 26.86 (9)°. Intra-molecular N-H⋯O and C-H⋯S hydrogen bonds both generate S(6) rings.

4-Methyl-N-[2-(pyridin-2-yl)ethyl-carbamo-thio-yl]benzamide.

In the title compound, C16H17N3OS, the dihedral angle between the planes of the benzene and pyridine rings is 71.33 (15)°. An intra-molecular N-H⋯O hydrogen bond is present.

Synthesis of isatin thiosemicarbazones derivatives: in vitro anti-cancer, DNA binding and cleavage activities.

New derivatives of thiosemicarbazone Schiff base with isatin moiety were synthesized L1-L6. The structures of these compounds were characterized based on the spectroscopic techniques. Compound L6 was further characterized by XRD single crystal.

(Z)-N-Ethyl-2-(5-fluoro-2-oxoindolin-3-yl-idene)hydrazinecarbothio-amide.

In the title compound, C(11)H(11)FN(4)OS, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules form chains through N-H⋯O hydrogen bonds, which are extended by N-H⋯S hydrogen bonds into an infinite three-dimensional network.

(E)-N-Ethyl-2-[(E)-3-(hy-droxy-imino)-butan-2-yl-idene]hydrazinecarbothio-amide.

In the crystal structure of the title compound, C(7)H(14)N(4)OS, mol-ecules are linked through N-H⋯S and O-H⋯N hydrogen bonds and C-H⋯S interactions, forming chains propagating along [21-1].

(Z)-2-(5-Chloro-2-oxoindolin-3-yl-idene)-N-methyl-hydrazinecarbothio-amide.

In the title compound, C(10)H(9)ClN(4)OS, an intra-molecular N-H⋯O hydrogen-bonding inter-action and an N-H⋯N inter-action generate ring motifs [graph sets S(6) and S(5), respectively]. In the crystal, mol-ecules form a chain through N-H⋯O hydrogen bonds, and these are extended by N-H⋯S hydrogen-bonding inter-actions into an infinite three-dimensional network. The crystal structure also exhibits weak C-H⋯π inter-actions.

Bis[2-(2-oxoindolin-3-yl-idene)-N-phenylhydrazinecarbothio-amidato-κ(3)O,N(2),S]nickel(II) dimethyl-formamide monosolvate.

The asymmetric unit of the title compound, [Ni(C(15)H(11)N(4)OS)(2)]·C(3)H(7)NO, contains one Ni(II) complex mol-ecule and one disordered dimethyl-formamide solvent mol-ecule. The Ni(II) ion is six-coordinated in a distorted octa-hedral geometry by two N, two O and two S atoms. An intra-molecular C-H⋯S hydrogen bond generates an S(6) ring motif.

(Z)-2-(2-Oxoindolin-3-yl-idene)-N-phenylhydrazinecarbothio-amide.

In the title compound, C(15)H(12)N(4)OS, the dihedral angle between the nine-membered indolin-2-one ring system and the phenyl ring is 2.72 (7)°. Intra-molecular cyclic N-H⋯O and C-H⋯S hydrogen-bonding inter-actions [graph set S(6)] are present, as are weak N-H⋯N inter-actions [graph set S(5)].

(Z)-N-Methyl-2-(5-methyl-2-oxoindolin-3-yl-idene)hydrazinecarbothio-amide.

In the title compound, C(11)H(12)N(4)OS, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol-ecules form a helical chain along the a axis through an N-H⋯O hydrogen bond. These chains are extended by an N-H⋯S hydrogen bond and a C-H⋯π inter-action into a three-dimensional network.

(Z)-N-Methyl-2-(5-nitro-2-oxoindolin-3-yl-idene)hydrazinecarbothio-amide.

In the title compound, C(10)H(9)N(5)O(3)S, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked via N-H⋯S hydrogen bonds into a zigzag chain along the b axis. C-H⋯O inter-actions are observed between the chains.

(Z)-2-(5-Fluoro-2-oxoindolin-3-yl-idene)-N-phenyl-hydrazinecarbothio-amide.

The title compound, C(15)H(11)FN(4)OS, crystallizes with three independent mol-ecules (A, B and C) in the asymmetric unit. The dihedral angles between the nine-membered 5-fluoro-indolin-2-one ring system and the benzene ring are 22.14 (11), 12.

Bis{N-ethyl-2-[3-(hy-droxy-imino-κN)butan-2-yl-idene]hydrazinecarbothio-amide-κN,S}nickel(II) dichloride.

In the title complex, [Ni(C(7)H(14)N(4)OS)(2)]Cl(2), the Ni(II) ion is six-coordinated in a distorted octa-hedral geometry by four N atoms from the two imine and two oxime groups, and two S atoms from the thione groups. Two chloride ions complete the asymmetric unit. In the crystal, mol-ecules are linked through N-H⋯Cl and O-H⋯Cl hydrogen bonds into an infinite chain propagating along [101].

Bis{2-[3-(hy-droxy-imino-κN)butan-2-yl-idene]-N-methyl-hydrazinecarbothio-amide-κN,S}nickel(II) dichloride.

The asymmetric unit of the title compound, [Ni(C(6)H(12)N(4)OS)(2)]Cl(2), contains two independent Ni(II) complex cations and four chloride anions. Each Ni(II) ion is six-coordinated in a distorted octa-hedral geometry by four N atoms from the two imine and two oxime groups and two S atoms from the thione group. In the crystal, the cations and anions are linked through N-H⋯Cl and O-H⋯Cl hydrogen bonds into infinite chains propagating along [10[Formula: see text]].

(Z)-2-(5-Methyl-2-oxoindolin-3-yl-idene)-N-phenyl-hydrazinecarbothio-amide.

In the title compound, C(16)H(14)N(4)OS, the dihedral angle between the nine-membered 5-methyl-indolin-2-one ring system and the benzene ring is 10.21 (7)°. Intra-molecular cyclic N-H⋯O and C-H⋯S hydrogen-bonding inter-actions [graph set S(6)] are present within the N-N-C-N chain between the ring systems.

(Z)-2-(5-Chloro-2-oxoindolin-3-yl-idene)-N-phenyl-hydrazinecarbothio-amide.

In the title compound, C(15)H(11)ClN(4)OS, the dihedral angle between the nine-membered 5-chloro-indolin-2-one ring system and the benzene ring is 10.00 (6)°. Intra-molecular cyclic N-H⋯O and C-H⋯S hydrogen-bonding inter-actions [graph set S(6)] are present in the N-N-C-N chain between the ring systems.

(E)-2-[(2,4-Dihy-droxy-benzyl-idene)aza-nium-yl]-3-(1H-indol-3-yl)propano-ate monohydrate.

In the zwitterionic title compound, C(18)H(16)N(2)O(4)·H(2)O, the dihedral angle between the planes of the benzene and indole rings is 39.20 (8)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif.

[2-(1H-Benzimidazol-2-yl-κN)aniline-κN]dichloridozinc.

In the title benzimidazole mononuclear complex, [ZnCl(2)(C(13)H(11)N(3))], the Zn(II) ion is four-coordinated in a distorted tetra-hedral geometry by an imidazole N, an amino N and two Cl atoms. The dihedral angle between the benzimidazole and benzene rings is 9.57 (1)°.

(2-{[2-(1H-Benzimidazol-2-yl-κN)phen-yl]imino-methyl-κN}-5-methyl-phenolato-κO)chloridozinc(II).

In the title mononuclear complex, [Zn(C(21)H(16)N(3)O)Cl], the Zn(II) ion is coordinated in a distorted tetra-hedral geometry by two benzimidazole N atoms and one phenolate O atom from the tridentate Schiff base ligand and a chloride ligand. The benzimidazole ring system forms dihedral angles of 26.68 (9) and 56.