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

Abstract

The catalytic activity of chitosan (Cs) and grafted Cs led to the preparation of terephthalohydrazide Cs Schiff's base hydrogel (TCsSB), which was then investigated as an eco-friendly biocatalyst for synthesizing novel thiazole derivatives. TCsSB exhibited greater surface area and higher thermal stability compared to Cs, making it a promising eco-friendly biocatalyst. We synthesized two novel series of thiazoles via the reaction of 2-(2-oxo-1,2-diphenylethylidene) hydrazine-1-carbothioamide with various hydrazonoyl chlorides and 2-bromo-1-arylethan-1-ones, employing ultrasonic irradiation and using TCsSB as a catalyst. A comparative study between Cs and TCsSB revealed higher yields than TCsSB. The methodology offered advantages such as mild reaction conditions, quick reaction times, and high yields. TCsSB could be reused multiple times without a significant loss of potency. The chemical structures of the newly synthesized compounds were verified through IR, 1 H NMR, 13 C NMR, and MS analyses. Six synthesized compounds were assessed for their in vitro antibacterial effectiveness by establishing the minimum inhibitory concentration against four distinct bacterial strains. The docking analyses revealed favorable binding scores against several amino acids within the selected protein (PDB Code-1MBT) for these compounds, with compound 4c exhibiting particularly noteworthy binding properties. Additionally, the in silico ADME parameter estimation for all compounds indicated favorable pharmacological properties for these compounds.

An Efficient Synthesis of Novel Aminothiazolylacetamido-Substituted 3,5-Bis(arylidene)-4-piperidone Derivatives and Their Cytotoxicity Studies

“…Thiazole-based compounds may be useful as inhibitors of multiple enzyme target inhibitors or some other metabolic pathways. , They are the most effective anticancer agent against the MCF-7 human breast adenocarcinoma and NIH/3T3 mouse embryonic fibroblast cell lines . New derivatives of thiazole were designed and synthesized as EGFR inhibitors affecting both MCF-7 and HepG2 cancer cell lines. − The results recommended that 1,3-thiazole is one of the most important therapeutic sites. − Antibacterial, antitubercular, antiviral, and anticancer activities are among the therapeutic areas where 2-amino thiazole is an important scaffold. New 2-amino thiazole scaffolds are phosphodiesterase type 5 regulators and COX-1/COX-2 inhibitors .…”

“… 23 − 25 The results recommended that 1,3-thiazole is one of the most important therapeutic sites. 26 − 31 Antibacterial, 32 antitubercular, 33 antiviral, 34 and anticancer 35 activities are among the therapeutic areas where 2-amino thiazole is an important scaffold. New 2-amino thiazole scaffolds are phosphodiesterase type 5 regulators and COX-1/COX-2 inhibitors.…”