New N(4)-methylthiosemicarbazone derivatives: Synthesis, characterization, structural properties, DNA interactions and antiproliferative activity

Five new thiosemicarbazone compounds derived from N(4)-methylthiosemicarbazide and 5-bromo-2-hydroxybenzaldehyde (1), 2,4-dihydroxybenzaldehyde (2), 3-ethoxy-2-hydroxy benzaldehyde (3), 3-tert-butyl-2-hydroxybenzaldehyde (4), and 2-acetylpyridine (5) have been synthesized. The molecular structures of the prepared compounds were identified using by single crystal X-ray crystallography. The binding properties of the compounds with calf thymus DNA were analyzed by UV, fluorescence titration, and viscosity measurements. The cytotoxic properties of the compounds were tested against human colorectal cell lines (HCT 116). The compounds showed greater pronounced activity than the standard reference drug 5-fluorouracil (IC50 = 7.3 μM). The results showed that the activity strength of these compounds depends on the lipophilic properties that provided by the terminal N(4)-substituent and aromatic ring-substituent, as well as the planarity that provided by the geometrical and conformational structures of the compounds

[2-(1H-Benzimidazol-2-yl-κN 3)aniline-κN]dichloridozinc

In the title benzimidazole mononuclear complex, [ZnCl2(C13H11N3)], the ZnII ion is four-coordinated in a distorted tetra­hedral 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)°. In the crystal, mol­ecules are linked by weak N—H⋯Cl hydrogen bonds into layers parallel to the bc plane. π–π inter­actions with centroid–centroid distances in the range 3.4452 (8)–3.8074 (8) Å are also observed

2-(5,6-Dihydro­benzimidazo[1,2-c]quinazolin-6-yl)-6-eth­oxy­phenol

In the title compound, C22H19N3O2, the phenol ring forms dihedral angles of 88.93 (10) and 87.95 (12)° with the benzimidazole system and the quinazoline benzene ring, respectively. In the crystal, mol­ecules are linked via O—H⋯N hydrogen bonds into infinite chains along [100]. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring

(2,2′-Bipyridyl-κ2 N,N′)chlorido(dl-threoninato-κ2 N,O 1)copper(II) monohydrate

In the title compound, [Cu(C4H8NO3)Cl(C10H8N2)]·H2O, the CuII atom is in a slightly distorted square-pyramidal coordination geometry with the basal plane defined by the two N atoms of the bipyridine ligand and the N and O atoms from the threoninate ion and the apical site occupied by the Cl atom. In the crystal, inter­molecular O—H⋯O, N—H⋯O, O—H⋯Cl, C—H⋯O and C—H⋯Cl inter­actions link the mol­ecules into a three-dimensional network. A π–π inter­action with a centroid–centroid distance of 3.461 (1) Å is also present

Ferrocene-1-carbaldehyde 4-ethyl­thio­semi­carbazone

The asymmetric unit of title compound, [Fe(C5H5)(C9H12N3S)], contains two crystallographically independent mol­ecules, A and B. The two cyclo­penta­dienyl (Cp) rings are parallel to each other in both mol­ecules, forming dihedral angles of 2.3 (3) and 1.0 (3)°, respectively, and adopt an eclipsed conformation. The mean plane of the semicarbazone group is twisted slightly away from the attached Cp ring in both mol­ecules, the dihedral angles between the mean plane and the Cp ring being 15.3 (2) and 10.8 (2)°. The ethyl group in mol­ecule A is coplanar with the mean plane of the semicarbazone group [C—N—C—C torsion angle = −175.2 (4)°], whereas it is nearly perpendicular in mol­ecule B [C—N—C—C torsion angle = 84.8 (6)°]. In the crystal structure, inter­molecular N—H⋯S hydrogen bonds link the mol­ecules into dimers. These dimers are further linked into chains via inter­molecular C—H⋯S hydrogen bonds. The crystal studied was a non-merohedral twin with a refined ratio of the twin components of 0.265 (2):0.735 (2)

2-(5,6-Dihydro­benzimidazo[1,2-c]quinazolin-6-yl)phenol

The asymmetric unit of the title compound, C20H15N3O, contains two independent mol­ecules, each of which is disordered over two sets of sites corresponding to a rotation of approximately 180° of the dihydro­benzimidazoquinazoline moiety, with refined site occupancies of 0.7479 (13) and 0.2521 (12) for both mol­ecules. The pyrimidine rings are in sofa conformations. In one mol­ecule, the hy­droxy-substituted benzene ring forms dihedral angles of 83.9 (3) and 82.4 (4)° for the major and minor components, respectively, with the mean plane of the benzimidazole ring system. The corres­ponding dihedral angles in the other mol­ecule are 88.31 (14) and 85.8 (6)°. In the crystal, mol­ecules are linked via inter­molecular O—H⋯N and N—H.·O hydrogen bonds into chains along [100]

Bis(1-ferrocenylmethyl­idene-4-phenyl­thiosemicarbazidato-κ2 N 1,S)zinc(II) monohydrate

In the title compound, [Fe2Zn(C5H5)2(C13H11N3S)2]·H2O, the ZnII ion is in a distorted tetra­hedral geometry being coordinated by two thio­semicarbazone ligands via N and S atoms. One of the Cp rings is disordered over two positions with occupancies of 0.55 and 0.45. The dihedral angle between the substituted Cp rings is 56.1 (5)° and the two phenyl rings are orientated at a dihedral angle of 41.7 (4)°. In the crystal structure, inter­molecular O—H⋯S, N—H⋯O and C—H⋯N hydrogen bonds link the mol­ecules into chains along the b axis. The structure is further consolidated by O—H⋯π inter­actions

4,4′,6,6′-Tetra-tert-butyl-2,2′-[1,2-phenyl­enebis(nitrilo­methyl­idyne)]diphenol acetone solvate

In the Schiff base mol­ecule of the title compound, C36H48N2O2·C3H6O, the central benzene ring makes dihedral angles of 46.64 (10) and 49.34 (10)° with the two outer benzene rings, and the two outer benzene rings form an angle of 39.13 (8)°. There are two intra­molecular O—H⋯N hydrogen bonds involving the two hydr­oxy groups, which generate S(6) ring motifs. In the crystal structure, the Schiff base mol­ecules are linked into a chain along the a axis by C—H⋯π inter­actions. The acetone solvent mol­ecules are attached to the chain via C—H⋯O hydrogen bonds

(E)-2-[(2,4-Dihy­droxy­benzyl­idene)aza­nium­yl]-3-(1H-indol-3-yl)propano­ate monohydrate

In the zwitterionic title compound, C18H16N2O4·H2O, the dihedral angle between the planes of the benzene and indole rings is 39.20 (8)°. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, inter­molecular hy­droxy and water O—H⋯O(carboxyl­ate) and N+—H⋯O(carboxyl­ate) and indole N—H⋯O(water) hydrogen bonds give a three-dimensional structure

Preliminary in vitro cytotoxic assay of human liver carcinoma cells (HepG2) of organotin(IV) complexes: Synthesis and characterization of organotin(IV) complexes of 2,4-dinitrobenzoic and 3,5-dinitrobenzoic acids

A total of five organotin(IV) carboxylate complexes was successfully synthesized and characterized quantitatively and qualitatively. Results of the infrared spectroscopy of the parent acids and complexes showed that the coordination took place via oxygen atoms from the carboxylate group. From the preliminary in vitro cytotoxic assay study, triorganotin(IV) complexes (2 and 5) were found to exhibit better activity as compared to diorganotin(IV) complexes (1, 3 and 4) but lower activity as compared to the reference drug. In addition, within the diorganotin(IV) complexes, monomeric type (3) exhibited a slightly better activity as compared to the organodistannoxane dimer types (1 and 4).Keywords: Preliminary in vitro cytotoxic assay, organotin(IV) complexes, comparison stud