Synthesis, Characterization and Cytotoxic Activity of S-Benzyldithiocarbazate Schiff Bases Derived from 5-Fluoroisatin, 5-Chloroisatin, 5-Bromoisatin and Their Crystal Structures

Abstract

Schiff bases were prepared from S-benzyldithiocarbazate with 5-fluro-, 5-chloro-and 5bromoisatin. All are potential tridentate nitrogen, oxygen, sulfur donors. They were found to be selectively active against MCF-7 cell line (Human non-metastatic mammary gland adenocarcinoma cell line). The bromide and fluoride compounds were the most active with IC50 values of 6.40 μM (2.6 μg/mL) and 9.26 μM (3.2 μg/mL) respectively while the chloride derivative was weakly active with an IC50 value of 38.69 μM (14.0 μg/mL). The cytotoxic activity of the halo substituted isatins against the breast cancer cell lines tested is in the order of Br > F > Cl. Planarity of the isatin ring in the Schiff bases can be arranged in the following order SB5FISA > SB5ClISA > SB5BrISA while the perpendicularity of the benzyl ring towards the dithiocarbazate plane can be ordered as follows, SB5FISA > SB5BrISA > SB5ClISA.

Synthesis, characterization and biological activity of Cu(II), Zn(II) and Re(I) complexes derived from S-benzyldithiocarbazate and 3-acetylcoumarin

“…The C12-S1 [1.775(3) Å ] was shorter in comparison to that in the complex solved by Carballo et al (2002), but it was longer than in the free ligand of most dithiocarbazate Schiff bases (ca. 1.66 Å ) (Manan et al 2011a), suggesting a predominantly thiol character in the complex. This conclusion was reinforced by the shortening of the N2-C12 [ca.…”

“…To expand our work on dithiocarbazate derivatives (Ravoof et al 2010;How et al 2008;Manan et al 2011a;Low et al 2014), we report new metal complexes with N 0 -[1-(2-oxo-2H-chromen-3-yl)-ethylidene]-hydrazinecarbodithioic acid benzyl ester (SBCM-H), a Schiff base formed by condensation of the S-benzyldithiocarbazate with 3-acetylcoumarin, a naturally occurring heterocyclic ketone having wellestablished pharmacological properties. The rationale behind this attempt was based on the prospect of developing synergistic effects from integration of the promising bioactivity of individual components (i.e., a metal center and its ligand comprising both the heterocyclic and substituted dithiocarbazate moieties).…”

Synthesis, Characterization, Crystal Structure and Molecular Docking Studies of a S-methyldithiocarbazate Derivative: Bis[2-hydroxy- benzylidenehydrazono) (methylthio)methyl]disulfide

“…The bond lengths and angles are within the normal ranges and are comparable to those in related structures. [50][51][52] The molecule adopts an EE conformation with respect to the C=N bond of the benzylidene moiety. The β-nitrogen and the thioether sulphur are trans located with respect to the C11-N3 and C8-N2 bond.…”

Preparation and Spectroscopic Study of New NS Ligand and its Cd(II) and Zn(II) Metal Complexes

“…These compounds warrant further study because they provide an interesting series of ligands whose properties can be greatly modified by introducing different organic substituents, thereby giving variation in donor properties and they are often biologically active [1][2][3][4] . Metal complexes and ligands contain pyridine have also been known to possess a wide range of anticancer, antibacterial, antifungal, antiamoebic and insecticidal activities [5][6][7][8][9] .…”