Dithiocarbamate-based novel anti-histaminic agents: synthesis, characterization, crystal structure and thermal study

• Published in: Dalton transactions : an international journal of inorganic chemistry 2024-08, Vol.53 (33), p.14077-14088
• Main Authors: Singh, Anupam, Kumar, Rajesh, Patel, Riya, Trishna, Gautam, Ram Nayan, Bharty, M K, Prasad, Lal Bahadur
• Format: Article
• Language: English
• Subjects: Antihistamines; Bonding strength; Chemical analysis; Coordination compounds; Crystal structure; Hydrogen bonding; In vivo methods and tests; Infrared spectroscopy; Ligands; Metal sulfides; NMR spectroscopy; Single crystals; Spectrum analysis; Structural analysis; Synthesis; Thermal decomposition; Thermal stability; Thermodynamic properties
• ISSN: 1477-9226; 1477-9234; 1477-9234
• DOI: 10.1039/d4dt01777c

A new -(4-fluorobenzyl) -(pyridin-2-ylmethyl) dithiocarbamate ligand ( ) having structural similarity to clinically approved antihistaminic drugs ( . pheniramine, chlorpheniramine, and brompheniramine) and its four metal complexes [Co(fbpm) ] (1), [Ni(fbpm) ] (2), [Cu(fbpm) ] (3), and [Zn(fbpm) ] (4) were successfully synthesized and characterized by various techniques elemental analysis, FT-IR spectroscopy, HR-MS, NMR spectroscopy, and absorption and emission spectroscopy. Furthermore, complexes 1 and 2 were characterized by single crystal X-ray diffraction. Complex 1 adopts distorted octahedral geometry around the Co(III) center while complex 2 adopts distorted square planar geometry around the Zn(II) center. X-ray data also showed various weak intermolecular C-H⋯F and C-H⋯N hydrogen bonding interactions leading to supramolecular architectures in complexes 1 and 2. The thermal decomposition study of complexes 1-4 analyzed by TGA shows that they are thermally stable up to 150 °C and also gives strong evidence for the formation of respective metal sulfides at higher temperatures. The antihistaminic activity of the ligand ( and its complexes 1-4 was examined against clonidine and haloperidol-induced catalepsy in Swiss albino mice of either gender in an animal model. The result shows that these synthesized compounds have antihistaminic potential to inhibit clonidine-induced catalepsy and may be targeted for different allergic conditions. Complex 3 showed maximum reduction in clonidine-induced catalepsy after 180 minutes of treatment when compared with the induced control.