Preparation, Characterization and Molecular Docking Study of some New Pyrazole Derivatives Derived from 2-Mercaptobenzothiazole.

Jassim, Jassim Abdalrazaq; Mohammed, Salim J.; Hameed, Zeyad A.

doi:10.33899/rjs.2025.187743

	Preparation, Characterization and Molecular Docking Study of some New Pyrazole Derivatives Derived from 2-Mercaptobenzothiazole.
Rafidain Journal of Science
Volume 34, Issue 2, June 2025, Pages 41-51 PDF (768.1 K)
Document Type: Research Paper
DOI: 10.33899/rjs.2025.187743
Authors
jassim abdalrazaq jassim^* ¹; Salim J. Mohammed^* ²; Zeyad A. Hameed^* ³
¹Nineveh Education Directorate
²Chemistry Department/ College of Science/ University of Mosul/ Mosul
³Department of Chemistry Sciences/ School of Natural and Applied Sciences/ Çankırı Karatekin University/ Turkey
Abstract
In this research, a series of pyrazole derivatives were prepared through a series of reactions starting from the reaction of the starting material mercaptobenzothiazole with ethyl cyanoacetate to prepare the thioester compound (1) and then reacting it with some benzaldehyde derivatives to prepare the α, β-unsaturated carbonyl compounds (2a-h) after which hydrazine is added to obtain the pyrazole derivatives. (3a-h). The prepared compounds were identified and confirmed by FT-IR and 1H-NMR spectroscopy. A comparative study was also conducted between finasteride, 5-alpha reductase inhibitor, and pyrazole derivatives through a computational comparative survey using molecular docking. Androgenetic alopecia (AGA) continues to be widespread skin issue caused by hormones, mainly due to dihydrotestosterone. The purpose of the current study was to prepare and evaluate the pyrazole derivatives as the 5α-reductase inhibitors responsible for DHT synthesis. Molecular docking uses the crystal structure of steroid 5α-reductase (PDB: 7BW1) to show that compounds 3a, 3c and 3b exhibit good MolDock and Rerank scores as well as strong hydrogen bonding with the active site of the enzyme. Among these, compound 3a has the highest binding affinity (MolDock Score of -172.891). The docking studies revealed crucial interactions between the docked molecules and the targeted enzyme amino acids, including conventional hydrogen bonds, π-stacking, and van der Waals forces, all of which stabilize the ligand-enzyme complex. The pyrazole derivatives can be used as a drug in AGA treatment as per results. Although, more laboratory and animal tests are needed to prove the effect and safety in humans of these medicines.
Keywords
Pyrazole; mercapto benzothiazole; thioester; finasteride; molecular duking

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