Synthesis, Characterization, Molecular Modeling, and Biological Evaluation of Novel Hydrazinylthiazoles With Anti‐Inflammatory and Antioxidant Activities
Sagar V. Tanpure, Abhijeet G. Mulik, Pravin C. Mhaske, Hemantkumar Akolkar, Vijay S. Koshti, Deepak N. Raut, Navnath T. Hatvate, Manohar D. Suryavanshi, Nirmala R. Darekar, Dnyaneshwar G. Karpe, Shamrao P. LawandeABSTRACT
An efficient, environmentally benign, and sustainable protocol for the one‐pot multicomponent synthesis of a range of bioactive new 2‐(2‐hydrazinyl)thiazole derivatives was achieved by using polystyrene sulfonic acid (PSSA) as the catalyst. The reaction between substituted 3‐aryl‐1H‐pyrazole‐4‐carbaldehydes, thiosemicarbazide, and various phenacyl bromides in water at room temperature rapidly yielded the new 2‐(2‐hydrazinyl)thiazole derivatives. The structure of the synthesized 2‐(2‐hydrazinyl)thiazole derivatives was characterized by various analyses, including FT‐IR, 1 H NMR, 1 3 C NMR and Mass spectroscopy. The PSSA catalyst effectively facilitated the synthesis of a novel series of 2‐(2‐hydrazinyl)thiazole derivatives, achieving excellent yields of 77%–85%. This method offers several notable advantages: room temperature reaction, a low‐toxic and inexpensive catalyst, high turnover frequency (TOF), a simple work‐up procedure, high yields, the use of an environmentally benign solvent system, high atom economy, and overall efficiency. These features make the protocol highly advantageous. The synthesized 2‐(2‐hydrazinyl)thiazole derivatives were screened for anti‐inflammatory activity, anti‐oxidant activity and were found to exhibit promising results, which were further supported by molecular docking studies.