Synthesis, Biological Evaluation, and Molecular Docking of Novel Azolylhydrazonothiazoles as Potential Anticancer Agents

Abstract

A novel set of thiazolylhydrazonothiazoles bearing an indole moiety were synthesized by subjection reactions of carbothioamide derivative and hydrazonoyl chlorides (or α-haloketones). The cytotoxicity of the synthesized compounds was evaluated against the colon carcinoma cell line (HCT-116), liver carcinoma cell line (HepG2), and breast carcinoma cell line (MDA-MB-231), and demonstrated encouraging activity. Furthermore, when representative products were assessed for toxicity against normal cells, minimal toxic effects were observed, indicating their potential safety for use in pharmacological studies. The mechanism of action of the tested products, as inhibitors of the epidermal growth factor receptor tyrosine kinase domain (EGFR TK) protein, was suggested through docking studies that assessed their binding scores and modes, in comparison to a reference standard (W19), thus endorsing their anticancer activity.

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

“…New thiazole derivatives 4a – f were obtained by subjecting equimolar amounts of thiosemicarbazone derivative 1 to an equivalent quantity of hydrazonoyl halides 2a – f ,,,, in the presence of Cs or TCsSB, as depicted in Scheme . Thin-layer chromatography (TLC) was used to monitor the progress of all of the reactions.…”

“…Treating compound 1 with 2-bromo-1-arylethan-1-ones 5a–f, ,,, employing CS and TCsSB as basic catalysts under the identical reaction conditions outlined in Scheme , resulted in the formation of thiazoles 7a – f as the ultimate products. Subsequently, we assessed the yield percentages of the resultant products 7a – f , as presented in Table .…”

“…Method A: A mixture of 2-(2-oxo-1,2-diphenylethylidene) hydrazine-1-carbothioamide 1 (0.283 g, 1 mmol) and either hydrazonoyl halides 2 ,,,, or 2-bromo-1-arylethan-1-ones 5 ,,, (1 mmol each) was prepared and then 15 mol % Cs was added. This mixture was exposed to ultrasonic waves at a frequency of 40 kHz and a power of 250 W for a duration between 15 and 50 min at a temperature of 35 °C.…”

“…Continuing our commitment to green chemistry research − and recognizing the biological significance of thiazole derivatives, − this study aimed to harness the catalytic properties of TCsSB to efficiently synthesize novel thiazole derivatives using an eco-friendly and sustainable approach. The study not only successfully synthesized these compounds but also evaluated their potential as antibacterial agents and drug candidates, providing valuable insights into their pharmacological properties and binding interactions with a target protein.…”

Structural Optimization, Anti‐TNBC Activities Evaluation, and Molecular Docking of an Indolone Derivative from Periplaneta americana

“…This characteristic holds immense potential for the development of diverse derivatives with varied frameworks, thus attracting significant interest in the field of medicinal chemistry. Particularly, thiazole derivatives have been found extensive utility in the design of antitumor agents such as (10R,13S,17S,E)-3- 21), [26][27][28][29] . Moreover, it has been further developed into clinically approved drugs such as dabrafenib (13), alpelisib (14), ixabepilone (15), and dasatinib ( 16), etc (Figure 1C).…”