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Abstract <p><b>Objective:</b> This study aimed to synthesize novel 1,3,4-thiadiazole-based 1-(amino(substituted-phenyl)methyl)naphthalen-2-ols using an ultrasound-assisted approach. The objective was to evaluate their anticancer and antibacterial activities, as well as their molecular interactions and pharmacokinetic properties. <b>Methods:</b> The compounds were synthesized using an ultrasound-assisted approach with silica sulfuric acid as a catalyst. This involved the condensation of aminothiadiazoles and aromatic aldehydes with 2-naphthol. Anticancer activity was tested against A-498 and A549 cell lines, while antibacterial activity was assessed against <i>S. aureus</i>, <i>B. subtilis</i>, <i>E. coli</i>, and <i>P. aeruginosa</i>. Molecular docking studies were performed with target proteins 1KZN, 1BAG, 1D7U, and 2XCT. Additionally, in-silico ADME profiling and structural analysis, including optimized geometries, FMOs, and MEP plots, were carried out. <b>Results and Discussion:</b> The synthesized compounds exhibited promising anticancer activity, with the bromine-substituted derivative <b>IVa</b> being the most potent. Compound <b>IVc</b> showed significant antibacterial activity against all tested strains. Molecular docking results indicated superior binding energies for <b>IVc</b> and <b>IVb</b>, ranging from −7.5 to −8.4 kcal/mol. <i>In silico</i> ADME profiling predicted favorable pharmacokinetic properties. Structural analysis showed that <b>IVc</b> had a reduced energy gap (∆<i>E</i>: 2.1687 eV), lower hardness, higher softness (ɳ: 1.0843 eV, S: 0.9222 eV), and low toxicity (<b>IVb</b>: ω: 0.3675 eV). <b>Conclusions:</b> The synthesized compounds, especially <b>IVa</b> and <b>IVc</b>, showed strong anticancer and antibacterial activities, making them promising candidates for further research. Molecular docking and ADME results support their potential for biological applications. Structural insights suggest that these compounds possess favorable reactivity, stability, and low toxicity, further confirming their potential as bioactive scaffolds for future investigations.</p>

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Synthesis, Anticancer and Antibacterial Activity, Molecular Docking, Pharmacokinetic, and DFT Studies of Some New 1,3,4-Thiadiazol Clubbed 1-(Amino(substituted-phenyl)methyl)naphthalen-2-ols

  • 期刊论文

  • 发表日期：

    2025年2月1日

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  • Onkar A. Lotlikar,
  • Siddhesh Jadhav,
  • Sreela Dasgupta,
  • Shailesh S. Gurav

摘要

Abstract

Objective: This study aimed to synthesize novel 1,3,4-thiadiazole-based 1-(amino(substituted-phenyl)methyl)naphthalen-2-ols using an ultrasound-assisted approach. The objective was to evaluate their anticancer and antibacterial activities, as well as their molecular interactions and pharmacokinetic properties. Methods: The compounds were synthesized using an ultrasound-assisted approach with silica sulfuric acid as a catalyst. This involved the condensation of aminothiadiazoles and aromatic aldehydes with 2-naphthol. Anticancer activity was tested against A-498 and A549 cell lines, while antibacterial activity was assessed against S. aureus, B. subtilis, E. coli, and P. aeruginosa. Molecular docking studies were performed with target proteins 1KZN, 1BAG, 1D7U, and 2XCT. Additionally, in-silico ADME profiling and structural analysis, including optimized geometries, FMOs, and MEP plots, were carried out. Results and Discussion: The synthesized compounds exhibited promising anticancer activity, with the bromine-substituted derivative IVa being the most potent. Compound IVc showed significant antibacterial activity against all tested strains. Molecular docking results indicated superior binding energies for IVc and IVb, ranging from −7.5 to −8.4 kcal/mol. In silico ADME profiling predicted favorable pharmacokinetic properties. Structural analysis showed that IVc had a reduced energy gap (∆E: 2.1687 eV), lower hardness, higher softness (ɳ: 1.0843 eV, S: 0.9222 eV), and low toxicity (IVb: ω: 0.3675 eV). Conclusions: The synthesized compounds, especially IVa and IVc, showed strong anticancer and antibacterial activities, making them promising candidates for further research. Molecular docking and ADME results support their potential for biological applications. Structural insights suggest that these compounds possess favorable reactivity, stability, and low toxicity, further confirming their potential as bioactive scaffolds for future investigations.