Metal‐Free One‐Pot Synthesis of 2‐(2‐Hydrazinyl) Thiazole Derivatives Using Graphene Oxide in a Green Solvent and Molecular Docking Studies

Abstract

An efficient, one-pot three-component reaction in the synthesis of a wide range of 2,4-disubstituted hydrazinyl thiazole scaffolds in ethanol at room temperature has been developed by the reaction of carbonyl compounds, phenacyl bromides, and thiosemicarbazide, using graphene oxide (GO) as a catalyst. The present catalytic method has many significant advantages such as shorter reaction time, broad substrate scope, low catalyst loading, environmentally benign solvent media, easy handling, and operational simplicity at room temperature. The products are identified based on their various spectroscopic data. The GO catalyst has a high reusability rate and is simple to recover. A mechanistic study suggests that the reaction takes place via a thiosemicarbazone intermediate, which is isolated and confirmed in this study using spectroscopic techniques. Thereafter, a molecular docking study has been performed to evaluate the binding affinity of hydrazinyl thiazole derivative as a possible inhibitor on the protein active site of human α-amylase and glucosamine 6-phosphate synthase[a] A

Green Biocatalyst for Ultrasound-Assisted Thiazole Derivatives: Synthesis, Antibacterial Evaluation, and Docking Analysis

“…Bacterial infections pose a significant global health challenge, and there is a continuous rise in associated mortality rates, as documented in references. , Therefore, it is essential to discover new antibiotics. Pharmaceutical drug development increasingly relies on nitrogen-containing heterocyclic scaffolds. ,− Numerous researchers have given the thiazole scaffold a great deal of attention due to its high medicinal value, which has promoted the design and synthesis of many compounds that contain thiazoles exhibiting a wide range of pharmacological properties, − with a notable emphasis on antibacterial activity. − Many articles have documented the production of derivatives of 2-hydrazinylthiazole − due to their significant relevance in the field of medicinal chemistry, , particularly in terms of their antibacterial properties. − The structure–activity relationships (SARs) of thiazole derivatives reveal that the presence of suitable substituents with electron-donating properties significantly influences the microbial resistance characteristics of the resulting compounds . Molecular docking is a crucial computational method employed to model the theoretical interactions between compounds and large molecular structures.…”

“… 14 , 28 − 30 Numerous researchers have given the thiazole scaffold a great deal of attention due to its high medicinal value, which has promoted the design and synthesis of many compounds that contain thiazoles exhibiting a wide range of pharmacological properties, 31 − 35 with a notable emphasis on antibacterial activity. 36 − 38 Many articles have documented the production of derivatives of 2-hydrazinylthiazole 39 − 41 due to their significant relevance in the field of medicinal chemistry, 42 , 43 particularly in terms of their antibacterial properties. 44 − 46 The structure–activity relationships (SARs) of thiazole derivatives reveal that the presence of suitable substituents with electron-donating properties significantly influences the microbial resistance characteristics of the resulting compounds.…”