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<p>A series of novel heterocyclic compounds based on 5-methyl-1-(<i>p</i>-tolyl)-1<i>H</i>-1,2,3-triazole-4-carbohydrazide were designed, synthesized, and evaluated for antioxidant activity. The synthesized derivatives included phthalimide (<b>NA-1</b>, <b>NA-2</b>), cyanoacetamide (<b>NA-3</b>), pyridine-based (<b>NA-4</b>), and hydrazonoyl cyanide (<b>NA-5</b> to <b>NA-8</b>) analogs. Structural confirmation was achieved through IR, NMR (<sup>1</sup>H and <sup>13</sup>C), and MS analyses. Antioxidant activity was assessed using the DPPH radical-scavenging assay, with ascorbic acid as a reference. Compounds <b>NA-2</b> (IC<sub>50</sub> = 0.072 ± 0.272&#xa0;mg/mL), <b>NA-5</b> (IC<sub>50</sub> = 0.029 ± 0.135&#xa0;mg/mL), and <b>NA-6</b> (IC<sub>50</sub> = 0.096 ± 0.085&#xa0;mg/mL) showed notable activity. DFT calculations suggested favorable electronic properties and hydrogen-bonding potential, supporting their antioxidant behavior. In silico pharmacokinetic analysis (SwissADME) showed acceptable drug-likeness with limited violations in some analogs with Lipinski’s rule of five, indicating acceptable drug-likeness. Bioavailability scores were generally 0.55, except <b>NA-7</b> (0.11).</p>

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Design, synthesis, and evaluation of novel triazole-based carbohydrazide derivatives with notable antioxidant activity: an integrated experimental and DFT study

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年2月23日

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  • Nagwan M. Rewish,
  • Mohamed R. Elmorsy,
  • Ahmed A. Fadda,
  • Safa A. Badawy

摘要

A series of novel heterocyclic compounds based on 5-methyl-1-(p-tolyl)-1H-1,2,3-triazole-4-carbohydrazide were designed, synthesized, and evaluated for antioxidant activity. The synthesized derivatives included phthalimide (NA-1, NA-2), cyanoacetamide (NA-3), pyridine-based (NA-4), and hydrazonoyl cyanide (NA-5 to NA-8) analogs. Structural confirmation was achieved through IR, NMR (1H and 13C), and MS analyses. Antioxidant activity was assessed using the DPPH radical-scavenging assay, with ascorbic acid as a reference. Compounds NA-2 (IC50 = 0.072 ± 0.272 mg/mL), NA-5 (IC50 = 0.029 ± 0.135 mg/mL), and NA-6 (IC50 = 0.096 ± 0.085 mg/mL) showed notable activity. DFT calculations suggested favorable electronic properties and hydrogen-bonding potential, supporting their antioxidant behavior. In silico pharmacokinetic analysis (SwissADME) showed acceptable drug-likeness with limited violations in some analogs with Lipinski’s rule of five, indicating acceptable drug-likeness. Bioavailability scores were generally 0.55, except NA-7 (0.11).