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<p>The rational design of multifunctional heterocyclic hybrids remains a key strategy in addressing antimicrobial resistance and oxidative stress-related disorders. In this study, a novel class of structurally integrated pyrazole–1,3,4-oxadiazole–thioacetamide hybrids incorporating a pyrano[2,3-c]pyrazole framework was synthesized via an efficient multistep protocol. Structural elucidation was accomplished using FT-IR, ¹H NMR, ¹³C NMR, and mass spectrometry. Biological evaluation revealed that several derivatives exhibited moderate to potent antimicrobial activity against Gram-positive and Gram-negative bacterial strains, as well as pathogenic fungi. Notably, compounds bearing strong electron-withdrawing substituents at the para position demonstrated enhanced activity, highlighting the critical role of electronic effects in modulating biological performance. Antioxidant assessment using the DPPH assay further indicated significant radical scavenging potential, with selected compounds showing competitive IC₅₀ values relative to the standard. Importantly, the present work introduces a previously underexplored hybrid scaffold that synergistically combines pyrazole, oxadiazole, and sulfur-based functionalities within a fused heterocyclic system. This structural integration provides a unique platform for tuning electronic distribution, lipophilicity, and target interactions, thereby enhancing biological efficacy. Overall, these findings establish the synthesized hybrids as promising lead candidates for the development of next-generation antimicrobial and antioxidant agents. This work aligns with the United Nations Sustainable Development Goals (SDG 3: Good Health and Well-being) by contributing to the development of novel therapeutic agents to combat infectious diseases and oxidative stress-related health conditions.</p>

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Design and Synthesis of Pyrazole–Oxadiazole–Thioacetamide Hybrids with Antimicrobial and Antioxidant Properties

  • 期刊论文

  • 发表日期：

    2026年5月9日

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  • Shweta Patel,
  • Ami Patel

摘要

The rational design of multifunctional heterocyclic hybrids remains a key strategy in addressing antimicrobial resistance and oxidative stress-related disorders. In this study, a novel class of structurally integrated pyrazole–1,3,4-oxadiazole–thioacetamide hybrids incorporating a pyrano[2,3-c]pyrazole framework was synthesized via an efficient multistep protocol. Structural elucidation was accomplished using FT-IR, ¹H NMR, ¹³C NMR, and mass spectrometry. Biological evaluation revealed that several derivatives exhibited moderate to potent antimicrobial activity against Gram-positive and Gram-negative bacterial strains, as well as pathogenic fungi. Notably, compounds bearing strong electron-withdrawing substituents at the para position demonstrated enhanced activity, highlighting the critical role of electronic effects in modulating biological performance. Antioxidant assessment using the DPPH assay further indicated significant radical scavenging potential, with selected compounds showing competitive IC₅₀ values relative to the standard. Importantly, the present work introduces a previously underexplored hybrid scaffold that synergistically combines pyrazole, oxadiazole, and sulfur-based functionalities within a fused heterocyclic system. This structural integration provides a unique platform for tuning electronic distribution, lipophilicity, and target interactions, thereby enhancing biological efficacy. Overall, these findings establish the synthesized hybrids as promising lead candidates for the development of next-generation antimicrobial and antioxidant agents. This work aligns with the United Nations Sustainable Development Goals (SDG 3: Good Health and Well-being) by contributing to the development of novel therapeutic agents to combat infectious diseases and oxidative stress-related health conditions.