Synthesis, crystal structure, molecular docking studies and bio-evaluation of some N ⁴-benzyl-substituted isatin- 3-thiosemicarbazones as urease and glycation inhibitors

Abstract

Fifteen N4-benzyl-substituted isatin-3-thiosemicarbazones 5a–o were synthesized and evaluated for their urease and glycation inhibitory potential. Lemna aequinocitalis growth and Artemia salina assays were also done to determine their phytotoxic and toxic effects. All compounds are potent inhibitors of the urease enzyme, displaying inhibition [half maximal inhibitory concentration (IC50)=1.08±0.12–11.23±0.19 μm] superior to that of the reference inhibitor thiourea (IC50=22.3±1.12 μm). Compounds 5c, 5d, 5h, 5j,k are potent antiglycating agents, showing glycation inhibitory activity better than that of the reference inhibitor rutin (IC50 values 209.87±0.37–231.70±6.71 vs. 294.5±1.5 μm). In the phytotoxicity assay, 11 thiosemicarbazones 5a–d, 5g, 5h, 5j–l, 5n,o are active, demonstrating 5–100% growth inhibition of L. aequinocitalis at the highest tested concentrations (1000 or 500 μg/mL). In the brine shrimp (A. salina) lethality bioassay, three derivatives 5b, 5j and 5o are active with median lethal dose (LD50) values of 3.63×10−5, 2.90×10−5 and 2.31×10−4 m, respectively.

Isatin-3-thiosemicarbazone as Chromogenic Sensor for the Selective Detection of Fluoride Anion

“…The synthesis of targeted receptor 2 was carried out according to the reported method [30]. As the synthesised receptor is a coloured compound, therefore colorimetric studies were carried out to check its ability to act as naked eye sensors for the anions via observing the color changes.…”

Crystal structure and Hirshfeld surface analysis of N-(2-chlorophenylcarbamothioyl)-4-fluorobenzamide and N-(4-bromophenylcarbamothioyl)-4-fluorobenzamide

“…Thiourea and its derivatives show a broad range of biological activities (Solmaz et al, 2018;Saeed et al, 2018;Pandey et al, 2019). The crystal structures of many thiourea derivatives and their metal complexes have been reported (Lai et al,2018;Contreras Aguilar et al, 2018;Fakhar et al, 2018;Mitoraj et al, 2018;Pervez et al, 2018;Hashim et al, 2017Ghazal et al, 2019Zhang et al, 2019). As part of our studies in this area, we now describe the syntheses, crystal structures and Hirshfeld surface analyses of the thiourea derivatives N-(2-chlorophenylcarbamothioyl)-4-fluorobenzamide (C 14 H 10 ClFN 2 OS, 1) and N-(4-bromophenylcarbamothioyl)-4-fluorobenzamide (C 14 H 10 BrFN 2 OS, 2).…”

Synthesis of New Oxindoles and Determination of Their Antibacterial Properties

“…Although in other research they evaluated several isatin-3-hydrazonothiazolines as urease inhibitors, despite some good results, substituents like 5-OCF 3 and 5-F over the isatin ring decreased the activity in various cases [33,34]. In a more recent research, Pervez et al reported several thiosemicarbazone-isatin derivatives with important activity as a urease inhibitors with lower IC 50 (0.87 to 11.23 μM) than thiourea (IC 50 � 22.3 μM) [35][36][37]. According to the abovementioned background about this kind of products, we have designed a series of isatin-pyrazole hybrids that could be effective as antimicrobials.…”