Spectral Characteristic and Preliminary Anticancer Activity in vitro of Selected Rhodanine‐3‐carboxylic Acids Derivatives

Abstract

Selected rhodanine‐3‐carboxylic acids derivatives were synthesized to determine the influence of the structure and the length of the linker between the carboxyl group and the nitrogen atom (N‐3) in the 2‐thioxo‐4‐thiazolidinone ring on their activity, monitored via interactions with human serum albumin. Based on fluorescence studies, we concluded that the length of the linker has a limited impact on these interactions. Additionally, we proposed the static mechanism of quenching for all the tested compounds. These derivatives seem to possess an anticancer activity in the nanomolar range with 3 as the most potent compound in both A2780 and A2780cisR cell lines.

Influence of 3-{5-[4-(diethylamino)benzylidene]rhodanine}propionic acid on the conformation of 5-(4-chlorobenzylidene)-2-(4-methylpiperazin-1-yl)-3H-imidazol-4(5H)-one

“…The conformation of the RA anion in (7) is different in comparison with the molecular structure of RA published earlier ( Fig. 4) (Stawoska et al, 2017). The rhodanine and phenyl-ring fragments connected by the methylidene linker in the RA anion are not as planar as in the RA molecule.…”

“…3-{5-[4-(Diethylamino)benzylidene]-4-oxo-2-thioxothiazolidin-3-yl}propionic acid (RA) was synthesized according to a five-step procedure described previously (Stawoska et al, 2017). The salt (7) of RA with (6) was obtained by dissolving both components in hot ethanol in a 1:1 molar ratio.…”

Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives

“…In the crystal structures of other rhodanine-3-alkylenecarboxylic acid derivatives determined previously, we often observed the characteristic homosynthons, built by two In the crystal structures of other rhodanine-3-alkylenecarboxylic acid derivatives determined previously, we often observed the characteristic homosynthons, built by two molecules connected into a dimer by strong hydrogen bonds O-H•••O formed by the carboxyl groups [28][29][30]41] or heterosynthons built by the carboxyl group and a solvent molecule [28,30]. In the presented crystal structures of /4a/ and /5a/, we have obtained homosynthons built by two molecules connected into a dimer by strong hydrogen bonds O-H•••N, additionally stabilized by C-H•••O contacts (Figure 3a,b).…”

Synthesis and Anticancer Activity Evaluation of 5-[2-Chloro-3-(4-nitrophenyl)-2-propenylidene]-4-thiazolidinones

“…The starting 2,4-thiazolidinedione 1a and 2-thioxo-4-thiazolidinone (rhodanine) derivatives 1b-l were obtained according to described procedures. We used three synthetic approaches to this end: (1) [2+3]-cyclocondensation of chloroacetic acid with thiourea (1a [11]) or ammonium thiocyanate (1b [12]); (2) dithiocarbamate method of 3-substituted 2-thioxo-4-thiazolidinone (rhodanine) derivatives synthesis (1c [13], 1g-l [14][15][16][17][18][19]); (3) the reaction of trithiocarbonyl diglycolic acid with amino compounds (1d-f [20,21]). Target Ciminalum-thiazolidinone hybrid molecules 2a-l were synthesized via the Knoevenagel condensation of (2Z)-2-chloro-3-(4-nitrophenyl)prop-2-enal and appropriate 4-thiazolidinone in the presence of sodium acetate under reflux in acetic acid (Figure 2).…”