Tuning the coordination properties of phenothiazine by regioselective introduction of diphenylphosphanyl groups

Abstract

The palladium and platinum complexes of the newly synthesized 1-(diphenylphosphino)-10-methyl-10H-phenothiazine (1) and the previously reported 3-(diphenylphosphino)-10-alkyl-10H-phenothiazine [alkyl = Me (2), Et (3)] and 4-(diphenylphosphino)-10-ethyl-10H-phenothiazine (4) were prepared. Density functional calculations were carried out to explain the electronic properties of compounds 1, 3 and 4. Compounds 1, 3 and 4 can interact with DNA, as was observed in agarose gel electrophoresis experiments. In addition, the cytotoxicity of the platinum complexes of ligands 2 and 4 towards breast, colorectal and hepatocarcinoma cell lines was studied.

Hierarchy of Supramolecular Arrangements and Building Blocks: Inverted Paradigm of Crystal Engineering in the Unprecedented Metal Coordination of Methylene Blue

“…The lowest unoccupied MO is instead an accessible π* level, favoring the N-atom reduction to an amide, with the system’s puckering due to the lost aromaticity. The acquired N basicity , is also consistent with the known N–H/N–R derivatives, also stable in the monoxidized form. , For the redox reversibility, promoted by the alternative glucose and O 2 reactants and the associated color change, MB is often used as an indicator . Other applications are in photocatalysis , and enzyme-catalyzed redox reactions.…”

Neutral and Cationic Palladium Complexes of P‐Stereogenic Phosphanes Bearing a Heterocyclic Substituent

“…Interestingly, for both isomers in the crystal the thianthrene moiety is folded such that it remains parallel to the C(20)–C(22) bond of the allyl group. The Pd atom is in a distorted square‐planar environment, the interatomic distances and angles of which are similar in the two isomers present in the unit cell and also similar to those in other Pd complexes containing five‐membered P,S chelate rings, such as in a complex with a 4‐diphenylphosphinophenothiazine ligand described recently by Silaghi‐Dumitrescu and co‐workers . The distance between the Pd atom and the C atom of the allyl group trans to the P atom is larger than with the C atom trans to the S atom, indicating a higher trans influence of the phosphinite group relative to the thioether group.…”

Synthesis, Characterization, and Biological Evaluation of Cu(II) Complexes Containing Triflupromazine with Glycine and Histidine

“…The interaction of these complexes with macromolecules such as DNA and BSA would explore their possible application as effective therapeutic agents. In addition, they are viable candidates for developing novel complexes with high biological activities and catalytic capabilities [8] …”

“…In addition, they are viable candidates for developing novel complexes with high biological activities and catalytic capabilities. [8] In the present work, two newly synthesized Cu(II) complexes composed of the heterocyclic primary ligand triflupromazine (TFP) and two different amino acids, glycine and histidine, as secondary ligands were synthesized and characterized. Additional experiments have provided information about bonding and potential geometrical structure through elemental analyses, IR, mass spectra, UV-vis, and magnetic susceptibility investigations.…”